Shoe Basics

Shoe styles that (almost!) every woman should consider adding to her wardrobe

When I worked as a stylist, I was always puzzled when I visited a client with a wardrobe full of lovely, current, perfectly-fitting clothing and a tiny mound of outdated, weather-beaten, unloved shoes that in no way align with their owner’s style. To me, appropriate, interesting shoes are an integral part of an overall look and I believe that knowing your preferred shoe types is absolutely essential to building personal style.

But not everyone feels that way. Despite the stereotypes about women and shoes, I think that many of us struggle to track down styles that suit our tastes AND lifestyles. Shoes get worn harder than clothing in most cases, and that makes buying them far trickier. A dress has to work with body shape … but shoes have to be comfortable, affordable, stylish, AND work perfectly with a multitude of outfits under a multitude of circumstances. So cultivating a lasting, useful, beautiful collection of shoes can be quite a project, and some women would rather focus on objects of style that require less versatility and research.

And since I know at least some of you readers are wondering how to get a great shoe wardrobe started, I went against my own grain and assembled a list of shoe types that I believe every woman should own. Or, at least, every woman who works in an office, academic, or similar environment and deals with seasons. If these lists may make your blood boil, I totally understand – but here’s hoping it’s a helpful resource for some!

pumpsCorso Como Del

Pumps: In my opinion, pumps are the most versatile style of shoe. They work for women of nearly all ages, heights, styles, and income brackets. The can be easily dressed up or dressed down. They come in a HUGE variety of styles, from sky-scraping heels to kittens, from snub toes to exaggerated points, and there’s something for every woman. A set of great pumps in your favorite neutral is a must.

ankle boot

Clarks Palma Rena

Ankle boots: This style is relatively new to the classic shoe cannon, but considering how long it’s been “trendy,” I think it’s here to stay. Ankle boots can be tricky to style, so look for a style that hits right at your ankle bone. Higher may throw off your proportions.

tall boots

Frye Parker Tall

Tall boots: Ahhh, I can hear the groans and grumbles already. But the fact is that tall boots are a classic style – again, working across many stylistic boundaries – and there ARE ways of tracking down a pair that fits. Even if you have narrow or wide calves, or can’t take a heel. No client has ever escaped my grasp without investing in a pair of tall boots. Again, go for your favorite neutral to start – black, brown, congac, or gray.


Dr. Scholl’s Really

Comfortable, stylish flats: Owning and wearing a variety of shoe heights is best policy for most women, and flats are a non-negotiable must. If oxfords irk you, try ballet flats or Mary Janes. There is a style of comfortable, flat, walkable shoe out there that will suit your exact style preferences.


Kork-Ease Adelaide

Comfortable, stylish sandals: Because your feet need to breathe in the summer, and having a pair that work equally well at the office and at the outdoor music festival is a fantastic feeling.

dressy sandals

Calvin Klein Loren

Dressy/fancy sandals: In my opinion, fancy sandals should cover two jobs. They should add sass to workweek outfits during the summer, but they should also be dressy enough for special occasion wear. There’s something about a sandal that makes it capable of crossover. Seek a style that has versatility; Metallics are great for this style of shoe. Black-tie-appropriate shoes may not be as versatile, but not everyone needs a pair of those. It’s super handy to have pairs that work for cocktail parties and more casual gatherings.

glitter pumps

Kate Spade New York Licorice

Dressy/fancy closed-toe shoes: Fancy happens when it’s cold and/or wet outside, too. So find a chic pair of dressy shoes that will keep your tootsies warm and dry. Ideally these shoes, too, should be capable of spicing up a workweek ensemble as well as taking you gracefully to an evening event.

red flats

Nine West SpeakUp

Red shoes of some sort: Many women prefer to keep red well away from their faces, but virtually every woman can do red shoes. And, as red is edging its way into neutral territory with every passing season, every woman should at least consider red shoes. You choose the style, heel height, and material. Just make sure that your base collection of neutral shoes includes one pair of bright red ones.

And those are the shoe bases that I believe every stylish woman should cover! You’ll notice that there are no snow boots or gym shoes on this list. That’s because those styles are activity-specific, and I assume that if you engage in those activities, those shoes will naturally work their way into your collection. Also omitted are casual wear-specific shoes. I don’t have weekend-only shoes because I use fun, interesting, slightly dressy shoes as a way to create unity between my work and weekend looks. And I encourage other women to do the same.

All images courtesy

**Disclosure: Actions you take from the hyperlinks within this blog post may yield commissions for See Already Pretty’s disclosure statement for more details. Sustainable options are either used, handmade, made in the U.S., artisan made in non-sweatshop conditions, or made using sustainable/fair trade practices.

Originally posted 2010-10-15 05:15:00.

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75 Responses to “Shoe Basics”

  1. RoseAG

    I change into my work shoes at work.

    Wine-colored pumps and black patent flats work with nearly everything so I stick to those at work.

  2. Frankincensy

    I don't work in a setting that would require smarter shoes, and walking is my default way of getting around, so nearly all my shoes are comfortable flats. I don't feel the need for more than a couple of pairs of heels for smarter occasions. Your list is still interesting, though, and makes me want to try tall boots sometime.

    My biggest stumbling block with shoes is that I'm a vegetarian and prefer not to buy leather if I can find a good alternative. (I don't mean to start an ethical debate here – I'm not going to tell anyone else they shouldn't wear leather, it's just a personal preference.) So far, this has left me with really cheap shoes made of synthetic leather that fall apart within months, because specifically vegan shoe brands seem to be really expensive (by my standards, at least). I probably need to search harder, because I'm sure there are attractive, durable and affordable vegan shoes out there.

  3. tracy

    Love this post, and totally agree on the red. I have red sandals, red wedges and red boots and find they are my most versatile shoes and really just complete any outfit.

  4. Cynthia

    Cool list. I have almost everything on there except fancy sandals. Really delicate sandals tend to make me look and feel topheavy.

    I'm most comfortable in a great pair of boots though. They make it possible for me to wear skirts and dresses in the winter and still feel warm. I'm starting to think it would be justifiable to have more pairs than I do (I was working with black, brown, grey, then picked up a pale beige earlier this summer) and to own (gasp) colored boots. I'm definitely feeling the influence of Sal in my boot life.

    Which reminds me, I have a boot purchase to blame you for. 🙂 I'll post a pic later today, after my haircut.

  5. Emma at Daily Clothes Fix

    Ah, shoes. For me they are one of life's loves – they look great, change up your outfit and fit you regardless of weight fluctuations.

    I agree with all the information here, although I certainly don't follow a "one pair" option for any of these.

  6. Sal

    Frankincensy: How do you feel about the synthetic suedes out there? I feel like they're nicer looking and feeling than some of the synthetic "leathers" and breathe better, too … maybe faux suede tall boots for you?

    Cynthia: Oooh, I'm a bad influence!

  7. BiblioMOMia

    A very good starter list! I agree with your first comments – when I see women on the street wearing something that just isn't quiiiiiiite right (close but not exactly great), the problem is ALWAYS with the shoes.

    And I certainly have more than 1 pair of all of these–eek!

    However, I wonder a bit about the omission of "casual" shoes. I'm a heels girl who spends most of her day in pumps or heeled boots, and I even run around after my baby in heels (and a whole assortment of fancy flats). But I'll be honest – I think it's precisely the casual shoe that trips women up. They have no idea what to wear to the playground, or running errands, or to pick the kid up at soccer – and we therefore end up with an entire group of women who wear ugly sneakers and danskos all the time (don't flame me for the danskos – I own a pair – but they have their place, and too many women rely ONLY on them for comfort).

    I'd love to see the addition of a casual flat – something like moccasins, TOMS, or topsiders. When I work on my friends' and sisters' closets, the addition of that type of shoe is exactly what brings them out of their shoe rut!

  8. Anonymous

    Sal- what are your thoughts on peep toe heels? Can they be worn year round?

  9. Samantha

    I don't really do pumps … not a huge fan of heels. It is thanks to you that I have tall boots I am in love with, though, and I have recently obtained a pair of Tsubo Acreas and a really, really cute pair of heeled Oxfords (Nine West) that I call my "librarian shoes". My problem with shoes is that I want to try more fun colors, but I have trouble finding styles I like in colors I like/that will work with stuff in my wardrobe. But I'm trying … you are indeed a bad influence. 🙂

  10. Sal

    Anonymous: In my opinion, yes, peep-toes can be worn year round. I pair them with tights myself, once it gets cold, but if you're in a warmer climate sheer hosiery or bare legs will work, too.

  11. Julia

    I like the list, and although it sounds reasonable, it's a hard one to fill out! I'm lacking a neutral pair of walkable heels and have wide wide feet.

    I'm terribly hard on shoes and wear them out (holes) within a year if I wear them regularly. It's a vicious cycle – I'm sure higher quality shoes would last longer, but since I've been wearing shoes out more often, I buy less expensive shoes more often. At some point I hope to invest in better quality so they last longer.

    Walkers out there: do people where one pair of shoes to walk to work in and then change at work? I've tried it, but then worry about how my walking shoes go with the daily outfit.

    Anyways, I like the list and would like to fulfill it at some point.

  12. Elizabeth

    I think I'm one of the women with ill-chosen falling apart shoes! For me, ballet flats and black Mary Janes are essential. I don't wear sandals cos of ungly feet.

  13. lauren.

    i've just started revamping my shoes in the past year. before i wore the same pair of birkenstocks every day in the fall/winter and flip flops in the summer. it was super hard for me to justify the cost at first of having a multitude of shoes, but now i am hooked! mostly i have flats and flat sandals, because i am both conscientious about my height/lack the coordination to wear heals. i have yet to try boots, outside of uggs, but i'm thinking i may have to. 🙂

  14. Rebecca

    I don't have a huge shoe collection. For several years, I worked in a pretty conservative environment, where I felt it was best to stick to basic pumps. I'm starting to get more pairs now, but decent shoes are expensive. Affordable clothes can be found easily, it seems, but good, affordable shoes are hard to come by.

  15. veejane

    For me, it's not a worthwhile shoe unless I can walk 3 miles in it. I have 2 pair of shoe-shaped ornaments at work for events, and a couple more at home for things like weddings, and everything else is shoes. Arch support, never a heel more than 2" (and usually flat), and I need strong mid-foot support: laces or straps or a shoe that goes all the way around the foot.

    I am not a fan of the "ornamental sandal" phenomenon, not just because they're impractical ornaments, but also because feet are funnylooking. The more you dress up the casing around your feet, especially open-toed and with significant heel, the more you draw attention to the fact that toes are not more than a stone's throw away from claws.

  16. JennyDC

    It's funny, I have no problem wearing green shoes, purple shoes, silver shoes, a fabulous pair of brown and turquoise Miz Mooz, but red? Can't picture it.

    I agree with BiblioMOmia about the need for decent casual shoes. Chunky athletic sneakers will ruin any look, outside of a gym. I think Privo, Skechers, and Naturalizer have some good casual shoes that still look at least a little stylish.

    Julia – I'm hard on shoes, too, but have found that one way to preserve them is to have lots, so you don't wear any one pair very often! I pay around $50 for most of my shoes, more for boots, and they last just fine. I don't think there's much difference between $50 and $100, quality-wise, for most shoes. More than that, they might be better, but I don't have much experience with more expensive shoes.

    And after reading today's post, I now want gray knee-high boots.

  17. Allison

    I love the look of tall boots, but I seriously battle an issue with extra-wide calves (at least by the boot standards out there, I love my calves!), does anyone know of where I can get a stylish boot that can accomodate?

  18. Rebekah

    I like my shoes non-leather and close to flat— which makes shoe-shopping much, much faster, if less often successful.

    You wrote a post about low heels last September (at my request— I felt so famous!), and your idea of "low" was still "high" to me. Cute shoes, though!

    I love colorful shoes, funky wingtips… I have a pair of Kenneth Cole Reaction mauve velvet low-heeled shoes with a low heel and pointy, jeweled toe. Sometimes our style shifts when we find something too fun NOT to wear.

  19. Scholar Style Guide

    Thank you, Sal, for bringing this up! For me, nothing ruins a great outfit like looking down and seeing the fine lady in a pair of worn-out shoes.

    I think this is a pretty comprehensive list. I also like how these categories allow room for parallel substitutions. For example, I don't own pumps because it's hard to find affordable comfortable ones… but my black wedges are a main staple. Or, I own red shoes, but I think any brightly colored shoe could fill that "box" just as well.

    I own shoes that fit all of these categories, actually. So I suppose I can stop shopping for shoes until one of my pairs needs to be replaced. : )

    (I'll disagree with JennyDC, though: I think you can make a big leap in quality if you're willing to pay $100 for a pair of shoes versus limiting yourself to $50.)


  20. Stefka

    The big limiting factor for me is that I need to wear custom orthotics about 99% of the time. I am in an outdoorsy nonprofit field, so this meant that I defaulted to hiking shoes for 15+ years! But during my style and wardrobe overhaul over the past 2 years, I've realized how many more options there are these days. My current work defaults are mary janes in the warmer months and clogs or boots in the colder months – all of which accommodate my orthotics. (And for special occasions, I've discovered how supportive and fun a 2" heel can be!)

  21. Sal

    CLEARLY I need to cook up a post specific to casual shoes.

    Oh, twist my arm …

  22. V

    Sal, I would dearly love to take your advice, but I have very wide feet. Triple wide for my left, and double wide on my right. I have no local shops that carry either of those widths and my one attempt at on-line ordering failed miserably, so now I have to go through the return by mail hassle.

    Nor do I feel the need to drive two hours just to shop for shoes that I'm pretty sure don't exist. If you can point me to a place that sells women's shoes in my width, I'll love you forever.

    At this point, my shoe-drobe consists of gray sneakers and black mens SAS shoes of the loafer variety. I've worn out my one pair of comfortable flats. Literally. Ditto for my one pair of boots (which never really fit in the first place). I can find no pumps that fit, feel good and that I'd want to be seen wearing in public.

  23. Sal

    V: Where have you tried online, lady? I know that, as someone with very wide feet, ordering shoes sight unseen is a risk … but retailers like Zappos and Endless give you free return shipping. Takes longer, but you're not paying extra for the joy of trying on a pair that don't work.

    Zappos goes up to 4EEEE, is that enough? There aren't any pumps in there, but a few cute boots, clogs, and Mary Janes.

    Anyone else have wide shoe resources to recommend?

  24. Stacy

    One of my friends little girls goes straight for my shoes when they come to our house…if that is any indication of how many shoes I have. 😉

    The only one up there that I don't really have is pumps. They just look too plain for me. Even in neutral colors I like the shoes to have some sort of fun design element.

    With the advent of internet shopping and sites like, and…anyone should be able to find shoes that suit their personal styles, though. Plus many have free shipping.

    Oh, and I have a pair of red boots coming in the mail to me today…yippee!

  25. angie

    Super write-up! I too believe everyone needs a red shoe of sorts 🙂

    My clients OFTEN have fussy feet which causes the mound of dated and beaten up footwear. In that respect it's a blessing that I have fussy feet too – because I totally get it and am very proactive about the challenges.

    To answer your question, as a fashion stylist I am somewhat expected to wear fabulous shoes (that’s a stereotype too). It has taken me years and lots of money to build up a collection of fab looking and comfortable shoes that work with my style – and more importantly my very on-foot lifestyle. I will not sacrifice comfort or aesthetics. The clothing is easy, but it’s hard work getting my footwear style sorted!

  26. Jackie

    I have entered severe "boot paralysis." There are so many styles and colors, and they're a big investment–so I just can't decide what to get. I have ten-year-old black boots that are still in okay condition, but have a big un-stylish square toe. I have some great brown boots my mother saved from the 70s–very cute but casual. So, what do I buy? Black, gray? Round toe or pointy? High or low heel? What's my most versatile choice.

    Oddly, when shoe paralysis hits, I just end up buying yet another pair of red shoes, on the theory that a woman can never have too many…

  27. Sheila

    I think this is a great starter wardrobe for shoes – I totally agree with the red shoes!

    However, I love variety in my shoes – I can't have a new pair unless it is totally different than what I already have in my wardrobe, whether in colour, style or some detail. I don't have more than 3 pairs of black pumps and they are all radically different, for example.

  28. Katie, Interrobangs Anonymous

    Lists like this are wonderful, but they also rarely fit into what I need in a shoe because it's so difficult to find the criteria I'm looking for within them.

    There are very few well-made leather-free options for those who don't want to wear animal by-products, there are even fewer narrow foot options (less than 1/3 of all the shoes at Zappos come in a narrow, and most of the time a company will not make both regular and narrow widths, so the majority of brands are off the table from the beginning), and I rarely see lists that aren't comprised of heeled shoes for the majority of the options. There's a growing number of women who have chosen not to wear heels because of the long-term and irreversible damage they do to the bones of the feet, hips and spine, but heels still make up the majority of what we're given as options to buy. Yes, not everyone will have the same considerations as me, but am I really such a minority?

    It's also worth considering the cost of shoes (especially for those of us who have specific needs like narrow feet or wide calves and cannot shop as easily from the regular options that dominate sales). It's often easier (and cheaper) to buy a new blouse or skirt than it is a new pair of shoes, so focusing on an even smaller list of basics and talking about how to care for your shoes once you've invested that much money in them are both additional points of consideration.

  29. LK

    Sal I have some advice for V and rest of us wide footed ladies 🙂 I can only buy about 2 brands of shoe because my feet are a small size (7) but wide. I go for Sofft which is a German shoe. Their regular is so wide I don't have to go up to a wide but they also make Wide Width. Super comfortable shoes, they are basically a sneaker in disguise. Other shoe is Merril. They aren't as pretty but they are great for someone on their feet all day.

    I use Zappos for both, highly recommend it. Shipping is free and overnight! You can't beat that. But I have also had luck with Shoemall. They carry both brands at Macy's stores.

  30. leah

    I'd probably like to add to your fabulous list and say that everyone who lives in a warm climate needs a pair of leather or fabric flip flops to replace the horrid rubber ones that have reached saturation where I grew up.

    Also, for casual shoes – don't overlook the humble low-cut Vans slip on or some nice bright white plimsolls. They can do the opposite of Sal's bridging trick and make something that is quite dressy look more casual (I wear them with vintage frocks on the weekend)

    I wholeheartedly agree with red shoes being included on the list. Black dress + stockings/tights + banging red shoes? Awesome and one of my favourite outfits.

  31. Bethany

    I would love a post on vegan shoe options. I'm trying to move toward that myself and it's really difficult to find cute shoes that aren't leather but are also comfortable and fit into my low level nonprofit worker budget. Especially boots! I bought a pair of nine west boots at an outlet last year, so excited that I was buying a "decent" brand. The fake leather is starting to fray near the zipper. Is that something I can get fixed or is it just due to my calves being robust?

  32. Diana

    This reminds me that I desperately need a new pair of pumps! (Although I hardly ever wear them… just for fancy occasions, really, and never to work. Same reason why the one item on your list I don't own is fancy closed-toe shoes.) I think you need to add short boots to this list!

  33. DaniellaBella

    I totally agree about having some red shoes. I think you just have a bit more sass in your walk. I walk about 10 blocks to work and I usually just wear my high heels. If they are super high or the heel is rather thin I wear a pair of black flat Camper shoes for comfort for the walk.
    I used to have such a hard time finding boots that would fit my shapely legs. For 10 years I was on the such for the perfect boots. I even wrote to Oprah for advice… She didn't answer. I found this website which allows you to order a calf width as well. The boots are expensive but I wear mine nearly everyday in the winter and have not regretted them for one second. I now have awesome tall boots!
    My feet haven't changed since I was 12 years old so I have amasses a collection. But I've learned that it's worth it to spend the money (or cheap on ebay once you know your size in a brand) on well made, interesting shoes!
    Shoes complete the look. I always feel like it's a waste to put effort into your clothes if you won't put equal effort into what is holding you up, causing you to stand proud!

  34. Sidewalk Chalk

    Thank you for this. I am one of those people who has fun clothes but worn-down crappy shoes. I was actually thinking this weekend that I need to buy a couple pairs, so thanks for a list of inspiration!

    – JoAnn

    Enter to win a 1960s vintage handbag!
    Sidewalk Chalk

  35. Laura


    I've been struggling to find different shoes, boots especially. All in the past two weeks I've got it in my head that I need to expand beyond my sneakers and flats. I have tall boots, but not something I want to wear everyday.
    I definitely think I'm in the 'neglect dept' when it comes to shoes!

    Any recommendations for ankle boots to wear with skinny jeans/leggings that aren't wide around the ankle or have a super high heel(3in +)??

  36. Sal

    Katie, Interrobangs Anonymous: Although the images used here are almost exclusively of heels, many of these categories of shoe could be substituted for flat or low shoes. Tall boots, comfortable stylish sandals, and red shoes … none of these need be heeled. Both "fancy" options could also be tracked down in low or no-heel options.

    As I've said ad nauseum, any set of suggested classic items or style "rules" of any sort should never be taken as gospel. These are merely guidelines and suggestions, and you can take, ignore, or adjust them as you see fit. You have chosen to avoid all heels, other women love to wear heels. To each her own.

    LK: You rule! Thanks for letting us know about the Sofft widths!

  37. katy

    this list is making me think i need to go shoe shopping….oh no!
    i don't believe i own a single pair of sandals…(other than a pair of chacos for adventuring…and i live in missouri, so we do get rather hot summers) but that's not because i haven't looked for any, none of the recent sandal-trends have caught my eye.
    i don't really agree with the red shoe statement. i have a few pairs of red shoes, which i bought mainly because i thought a good shoe wardrobe should have some, and i can't remember the last time i wore any of them. red (and orange) are my least favorite colors though, so it's understandable. perhaps instead of red, just a brighter/bolder colored shoe that works well within the rest of the wardrobe. for me: yellow and to a lesser degree teal, as my basic neutral is grey (sometimes navy).
    i've been on the lookout for tall boots for two years now! i have good sized calves, but fit into most boots just fine, but my ankles are tinytiny, and i have the look/feel of boots that are so big around my ankle – thick socks won't help, because then the calf bit won't fit. even zip-up boots seem to have swimmy ankles. if you know of any heel-free boots, or just good/comfortable brands of boots that tend to have more fitted ankle areas, i'd love to know. i've been yearning for a nice pair of grey boots, flat (not even the little cowboy heel), that are well fitted and would look good with skirts/dresses, and can be walked in for miles, but haven't found any in two years of looking. i think i just might have to learn how to make shoes in order to get some!

    good list – i'm going to have to double my efforts to hunt down some decent sandals and good boots….

  38. Tina

    V, I get you. I have EEE width feet and I wear a size 5. I have extremely high arches, so arch support is a must. And I also have weak ankle ligaments, which MRIs and x-rays and physical therapy up the wazoo have convinced me to stay away from heels (I am very very prone to ankle turning). Basically, my feet are my problem children. I have no words of advice except that I feel your pain. I HATE shoe shopping, online and in stores, because it gets me very depressed. I have a closet full of cute boots and heels and pumas and ballet flats that I can no longer wear – one day causes a week worth of pain.

    I console myself that I still love my feet and I like to look at them during yoga. And the rest of my body is problem-free clothes-wise, but I do envy the rest of you!

  39. fashion herald

    For those of you looking for inexpensive green and non-leather options, try the Zoe & Zac line at Payless. I don't own a pair so I can't comment on wear and tear, but from trying them on in stores they seem comfortable.

  40. pretty

    This post is a very interesting one for me. I LOVE shoes, but I struggle majorly with them. The thing about shoes, is I can't get them cheap because I need good shoes for my troublesome feet. Last week, I was ordered to buy new shoes by my DOCTOR! xx

  41. Emily

    I want to second LK's recommendation of Sofft and Merrell but I disagree that Merrells can't be cute! I own a pair very similar to their current 'Petunia' style (a leather wedge) and despite wearing all manner of crazy shoes – from 5-inch snakeskin heels to cowboy boots – those Merrells have garnered me more compliments than anything. They feel more casual than they look! An extra bonus too for ladies who have to walk in the ice and snow: the adorable petals on the sole of the 'Petunia' grip like nobody's business. So in the winter they look pretty dressy with a nice wool coat and tights because everyone else is in big ole snow boots!I can't recommend them enough.

  42. Crystal

    I have to know what brand those tall boots are? They look like my faves, Frye Rory, but I'm kinda hoping they are something different and cheaper so I can buy them!

  43. purpleshoes cannot actually find purple shoes.

    So I wear a size 12 narrow, a size in which there exist exactly one pair of ballet flats. And I have never bought a pair of shoes for less than $60; one of the reasons why I keep wearing the same mary janes until the straps fall off is because $150 is about mid-level for casual shoes in my size.

    It's hard, fellow weird-shoe-size people! Zappos is our friend, but even so, I hope no one gets sick of seeing the same loafers over and over.

  44. Carmen

    I love the suggestions however I can only wear flat shoes. I mean it. I have turned an ankle every 2 years since I was in the fifth grade. I have broken a bone on both feet. I man flat-footed and I pronate my ankles. This has been a stylistic annoyance ever since I started caring about fashion. Many of the turned ankles have been from shoes with heels so I just don't do it anymore. Kitten heels are weirdly the worst b/c they tend to have such a tiny little heel. I can sometimes get away with a platform-type shoe IF they have a wide base. Platforms with narrow bases just ask for trouble.

    It's sad. Imagine what NEVER wearing heels would do to your wardrobe. 🙁

    But I haven't broken any bones in awhile, 🙂

    All that being said I LOVE my tall black boots even though they are flat and I just recently bought some red flats that I have gotten a ton of mileage out of b/c they really do give pop to so many things. And I don't own a single red shirt!

  45. Julia

    I've had luck with

    They have detailed instructions on measuring calves and what to do if you're between sizes, etc. Each boot listed also has calf measurements specific to each size.(more details than other websites)

    Unfortunately, there is a flat shipping rate of $14.95 and you pay for return shipping as well. However, the measurements are pretty good to prevent returns. Also, you can check out the boot and sizes on that website and order them on zappos or somewhere else.

    They have a wide variety of boots (some are pricey).

    A problem with widewidth calf boots is that shoemakers often assume that large calves = large ankles. Then the boots fit up on the calf bulb, but are baggy everywhere else. This is something that is hard to tell without trying on.

  46. Ann V

    Munroe shoes makes tall boots with stretch leather uppers that are awesome for people with hard to fit calves. They're super comfy, too.

    I am another one of those people with difficult feet. Shoes that work for me are hard to find, and when I do find them they're very expensive. I try my best, but I probably have a smaller and more casual shoe collection than average. (But I do have a red pair!) I'm okay with that, because I need to keep my feet healthy. I'm very conscientious of it – I look for other ways to dress up my outfits and I always consider my shoes when selecting clothes.

  47. Sal

    You gals with hard-to-fit feet and calves, I hear you! I've already got a post in the queue about specialty sizes. And some of your fellow readers have left great tips right here in the comments.

    I know you're so frustrated, and ugh, it just makes me want to kick things that you can't find stylish shoes you love that fit and don't hurt.

    One of my dear friends shattered the bones in BOTH her feet on separate occasions, and has such a horrible time finding shoes that don't make her cry in pain. She can't do flat flats, but definitely can't do heels. It's a constant battle for her.

    I'll always keep my eyes peeled for more resources.

  48. Megan Mae

    I totally agree with this post. I have no need for a dressy sandal in my life. I'm sure that's different for a lot of people.

    I rarely wear sandals even in the summer months of Southern US because everywhere pumps air conditioner and I spend very little time outside. And special occasions taking place in the summer months is even rarer.

  49. Katie, Interrobangs Anonymous

    Sal: Any frustration you heard in my comment wasn't directed towards you or what you suggested, but towards the shoe industry as a whole – an industry that (for understandable reasons) tends to cater to common factors.

    For example, I'm not upset that you used images of heeled shoes, I'm upset at how few un-heeled options there are compared to heeled shoes, especially when you factor in difficult to fit sizes and widths, alternative materials, cost (as soon you as have less-common criteria, price goes way up) and the desire to not have your shoes look like the ones your grandma wears. These lists become frustrating for many people because our response is, "Yes! Those are just the sort of things I want to wear. But I can't find them."

  50. CompassRose

    I agree with the red shoes need – but really, it is HARD to find a pair of really nice red shoes or boots that are well-made, and the "right colour" of red.

    Far too many red shoes are (for me): too slutty, too shiny, too pointy, or, in the other direction, too whimsical, cute or adorned with stupid flowers or bows; made of weird non-leathers and lined with gross polyester padding; or otherwise Just Plain Wrong.

    Not to mention, in my conservative little corner, the red shoe rarely appears in the first place.

    I'm desperate for a red boot right now (well, to be specific, I'm desperate for the Fiorentini & Baker Eli in red, but that is – uh, probably not happening, since they'd cost more than my rent). But really I've been looking for Mr. Right Red Shoe (Boot) for at least three years now.

  51. tinyjunco

    i can't comment on this list – i've never approached my wardrobe that way….but i do loooooove me some shoes! and i don't have problem feet, it's more like 'problem big toe up to somewhere around the waist'.

    one approach is to stick with whatever type of shoe works with your body and your style, and get multiple variations on that shoe. i had a friend, KJJ, who wore ankle boots with ~2" heels exclusively. black, brown, grey, suede, patent, ostrich, chunky heel, curvy heel – she had about a dozen pair. she looked great and it was so fun to see how much variety there was within such set boundaries. she made it her trademark and it made a big impact on her personal style.

    some people branch out a lot in their style, while others tend to 'specialize'. it's so frustrating to be limited by your body. but from the style point of view, you can really turn it to your advantage.

    and big hugs to everybody posting sources!! steph

  52. Frances Joy

    Love this post and love shoes more than I should. I agree with BiblioMOMia – the casual shoe thing stumps me. I hate wearing sneakers for anything but working out and that means I wear my heels a lot for occasions when everyone else is wearing sneaks and ballet flats (I still haven't found a comfortable pair of those, either). My mom recently gave me her boat shoes, but besides those, I have pretty much zilch when it comes to casual shoes and I just don't know what to do.

    Please, please do a post on casual shoes! I'm moving to the rainforest – not even joking – and my assortment of pumps and heeled sandals just isn't going to cut it.

  53. orchidsinbuttonholes

    Such a great starter list, Sal. I most love how you emphasize versatility – that fancy shoes can sass up an every day outfit as well as work for a swankier night out.

  54. lisa

    Loved reading this list and the comments that followed! Like a couple of the commenters, I think a casual sneaker alternative that doesn't look like a running shoe should also be on the list. It makes SUCH a difference to wear a sleek-looking, fun sneaker when you're taking the dog for a walk or going to the grocery store instead of a pair of Nikes or something. I'm partial to canvas slip-ons and lace-up Keds myself.

  55. Stephanie

    Fun to read and look at the pictures but for me casual shoes are a must. I like the red idea though as my favorite shoes are rasberry colored jambu mary jane like things. I think so much depends on lifestyle though just like I invest more in my jeans then my dress clothes I invest more in my go to casual shoes and don't even own a pair of pumps.

  56. ycleped

    Frankincensy, check out Fluevog and Clockwork Couture. They both have non-leather options that are gorgeous, and I can vouch for the quality of Fluevogs. They will last forever!

  57. Katrin

    Well, first the shoes have to fit. I suppose I should count myself lucky to wear the very largest size most stores sell (US10/UK8), and not any bigger. Still many styles run small, especially the dressier ones.

    Then I have to consider whether they'll still fit after I put the arch supports in them for my plantar fasciitis – not even thinking yet about whether the supports will show (and how much I can afford to care if they do). Then…what if I want to wear socks?

    Assuming the shoes actually fit on my feet after all that, I have to think carefully every day, no matter what shoes I'm wearing, about how much walking I'm likely to do and where. Sturdy boots can end up feeling like a prison or flimsy little flats can get painfully unsupportive at the end of the day, no matter how comfortable and appropriate they started out.

    All this and we haven't even touched on whether the shoes are a style I like.

    I have a decent if minimal collection of shoes that serve well for most occasions. I try to maintain them in good condition and repair them when needed, because I don't relish having to try to replace them.

    Just looking at some of the shoes you feature makes my feet hurt.

  58. Inder-ific

    Your basic principles could easily be adapted for someone who never or rarely wears heels. Flat boots are really cute, as are flat pumps, flat sandals, etc. I wear low heels or flats most days (just because), and I've never seen this as a major obstacle in shoe-shopping. (I admit it's harder to find special occasion flats.)

    Whatever shoes you wear, it's nice if it looks like you thought about your selection before you put them on! That's more important than actual heel height in my opinion.

  59. Anonymous

    Sal, I'm a long-time admirer of your blog, and this posting was particularly compelling b/c I'm a shoe-lover too.
    I have another suggestion for those with wide calves – there's a company called Duo Boots in the UK that specializes in custom fittings for tall boots. I ordered a pair for my birthday several years ago and the quality was excellent.

  60. Jessoca

    I agree with your list, though I hardly do sandals at all for some reason. I just bought a pair of red patent leather pumps this week, Alfani brand from Macys with only a 2.5" heel – I had been wanting a pair for fall!

    I like the interesting shoes you wear – it has introduced me to several brands that I had never heard of locally!

  61. Mindixy

    Great post! I bought a pair of red peep-toe slingbacks a couple of years ago thinking that I would probably only wear them with one outfit. But they were a steal so I grabbed them. I was shocked to find out just how much I wore that pair of shoes! They're completely worn out now and I am looking for a replacement pair.

  62. Ivy

    I'm working on my list–so far, my list is tall boots in my neutral(s), shorter boots for transitional seasons, high heeled Mary Janes or T-straps, and flat/low-heeled Mary Janes or T-straps. And eventually a few pairs of cute colored shoes in the colors I wear a lot.

    I don't include pumps because I can't wear them–I have orthotics and they raise my foot high enough that I walk right out of the shoe. Alas.

    The biggest thing for me is the cost. I know good shoes will last and I do stalk sales but it's still hard for me to bring myself to spend so much money at once.

  63. rb

    I'm definitely a Person of Shoe, so of course I have all these styles. I would add flat sandals and flat boots for summer and winter casual wear, respectively. I don't really think red shoes are for everyone – my favorite shot of color on the foot is purple. (but of course I have red, too.)

    I wonder, don't you also run into people with great shoe wardrobes but ho-hum clothing wardrobes?

  64. melina bee

    may I ask the brands of the second pair of shoes pictured? green with wooden colored heels? those are very fabulous.
    I love your list. I have waaay too many shoes b/c it's so easy to thrift a fun pair. Sadly I am working on the versatility aspect of the shoe wardrobe.

  65. Sal

    Hey friends, I'm so sorry – this is not like me – but I didn't keep any of the shoe style names from this post. They're all from Zappos, but I can't recall brands or styles. Apologies!

  66. CompassRose

    For those who are skinny of ankle and looking for low boots you can walk in, you might consider that the flat lace-up Victorian schoolkid/work boot (like this Jeffrey Campbell: ) is coming right back in, and there are quite a few nice ones making their way into stores. Or you could probably thrift a nice pair from the late 80s, if you were so inclined.

  67. The Waves

    Your list seems pretty comprehensive. I am not a huge fan of pumps myself, but certainly see their usefulness. My must-haves would have included flat boots and "tough" ankle boots – but I fully understand that it is a personal style preference and that they might not suite all. I love that you put red shoes on the list – they are indeed an absolute must!

  68. Anonymous

    As a woman who holds a job where she cannot wear heels (or open-toe shoes of any kind), I have to say that as much as I'd like to be able to invest in so many fun shoes, I'd have almost no chance to wear them.

    I'd very much like to see an article featuring "casual" shoes, preferably ones that can stand up to long workdays in all weather occasions.

  69. DoBatsEatCats

    I agree with Frankincensy — with the added twist that I have screwed-up feet from wearing pointy shoes when I was young. Vegetarian + car-free (therefore walk everywhere) + screwed-up feet = it's nearly impossible for me to find decent shoes that don't cause pain. Heels are pretty much entirely out unless I'm headed to a night out in our neighborhood so I don't have far to walk. I pretty much live in sneakers or, in summer, the one pair of really comfy sandals I was lucky enough to find. (and yes, I bought multiples!)

    In other areas of my wardrobe I am making an effort to get out of my (literal) comfort zone and put forth a little more effort, but with shoes, I just can't push through the pain. I wish I could!

  70. Katie

    Do you happen to remember the brand and/or name of the tall boots you featured in your post? I’ve been looking around for a pair and I love these!

    Also, normally I hate lists like these, but I actually agree with everything you have listed!

    • Sal

      Oooh, Katie, I don’t remember the model name but they’re Frye boots for sure and I know they’re still for sale on Amazon and the like!

  71. Laura (dusty_rose)

    I just found this post through one of your more recent posts, and while it doesn’t exactly make my blood boil, it does bother me–because of the statement that *all* women who work in certain fields should have these shoes, regardless of personal style or circumstance.

    Personally, I have extra-wide, flat feet. I’ve gone into specialty stores and tried on literally dozens of pairs of shoes before finding one that fits. Sure, I could buy online from a place like Zappos that has free returns–but lugging dozens of shoe boxes to the post office doesn’t sound like fun. I just did that with bras, and it was the hugest hassle. Enough to make me give up on bra shopping for a long, long time.

    Flats don’t have enough support for me, and they never fit right anyway–even if they’re extra-wide, there’s always a blister-inducing gap in the back. It’s just the way my feet are shaped. Heels? I just can’t wear them, period, unless it’s for an hour at a party. So I stick with my one pair of sneakers, one pair of Naot Mary Janes (which are super-comfy except when my plantar fasciitis is acting up), and two pairs of sandals, plus a few less comfy but cuter shoes to wear on rare occasions.

    My Naots were about $100. I’ve been lucky that my parents buy me a new pair when the old ones wear out, but I can’t exactly ask them to fund a major footwear habit, nor can I afford to buy multiple pairs of $100+ shoes myself. Cheap shoes, for me, are a thing of the past. I used to love all my cheap, ill-fitting shoes in high school: platform Mary Jane sneakers with rainbow soles! Black platform sneakers with pink and silver flames! Leopard creepers! Strappy sandals with star-shaped studs!

    But as much as I miss wearing awesome shoes, I’ve come to accept that being good to my feet is more important. Especially since I live in a city without a car, so going anywhere involves at the very least a 10-min. walk to the subway (and I carry enough stuff that lugging shoes around is a hassle I’d like to avoid). Especially now that I’ve started getting plantar fasciitis. I’ve seen how much feet can hurt, and I would do anything to prevent that, style be damned.

    As for stuff like red shoes, or tall boots–sure, I’d like to have them, if I could find ones that fit. But they’re not everyone’s style. And I am really, really not ok with saying everyone should own one particular type of shoe, no matter how awesome that shoe is. I mean, some people just don’t like red! Why force them to wear a color they don’t like?

    I think this list itself isn’t inherently bad–it just would have been much better framed as “Here are a few common types of shoes that can be useful to have if you work in XYZ environments” rather than “You MUST have these shoes, regardless of whether you like them and whether you have the time/energy/money to put into finding them, and whether it’s even possible for them to be comfortable on your particular feet.”

  72. Laura (dusty_rose)

    Also, I have a problem with statements like, “To me, appropriate, interesting shoes are an integral part of an overall look and I believe that knowing your preferred shoe types is absolutely essential to building personal style.”

    For some people–especially those without foot problems or hard-to-find-sizes–shoes are an integral part of their overall look. For others, the time/energy/money/pain just isn’t worth it. If someone wants to look at me and think I look insufficiently put-together, or even that my outfit is “ruined” by my sneakers, as one commenter said above, fine. They have a right to judge, and I have a right to think they’re being jerks (or at the least, inconsiderate).