Reader Request: How to Find Your Perfect Boots

How to shop for and buy your perfect pair of boots

Reader Kimbra sent me this request:

I was hoping you could point me in the right direction for a pair or two of fiscally conservative multi-purpose boots. The type that can be worn with a pair of jeans or a skirt as well as either keep my feet warm or have room for thick socks. For example, at work I am on my feet most of the day as well as inside/outside so a versatile pair of boots appropriate for indoors and outdoors that can be worn with jeans or something more professional would rock my world.

Now, Kimbra’s needs are fairly specific and probably don’t apply to each and every one of you fabulous readers. But as I was responding to her request, I realized that I had concocted a set of questions that could be used by ANY woman to locate her ideal pair of boots.

So, if you’re questing for a new pair this season, ask yourself:

  1. What’s my preferred style? To me, the shape of the boots shown above represents the tall-boot baseline. Those beauties are the Calvin Klein Selma boots, and they’re a far cry from “fiscally conservative,” but you can find similarly-shaped boots just about everywhere: Tall shaft, medium heel, solid color including the heel and sole, absolutely no detailing. Even if those boots look far too dull for your taste, it’s best to begin with a very plain, sleek, pared-down design and THEN start adding embellishments like buckles, slouching, exposed zippers, etc. Build your perfect boot in your mind, then see if you can find something similar in the shops or online.
  2. Which neutral will I wear most? For most women, it’s black. But cognac brown goes with EVERYTHING and generally looks more expensive.
  3. Is a heel practical? If you are on your feet all day then super-tall heels are right out, but can you deal with 1″ or 2″? Are you better off with a flat/riding boot style? Or will these be boots that never walk more than five blocks at a time?
  4. Are your feet fussy? High or fallen arches? Bunions or corns? Need loads of support or flexible soles? Read customer reviews, check construction, ask questions, do everything you can to make sure that your potential new boots will caress and love your fussy feet.  (Check Barking Dog Shoes’ boot recommendations for some ideas.)
  5. Do I have fitting concerns? If you have wide or narrow calves, small or large feet, or any other traits that make boots tough to fit, you may prefer to shop in person. But if not, I highly recommend going online. I’d try scouring Zappos and Amazon. The first two will allow you to refine your search and hunt down styles that you really love. Amazon makes the hunting harder, but has KILLER deals. If you find a style on Endless or Zappos, check Amazon to see if you can get a better deal.
  6. What’s my budget? Multi-purpose boots can be bought cheap, but real leather and quality construction will last longer and be kinder to your feet. Still, never, ever spend more than you can truly afford.

If you run through these questions before clicking “buy,” you’ll have a much better shot at finding a pretty-darned-close-to-ideal pair of boots for yourself!

**Disclosure: Actions you take from the hyperlinks within this blog post may yield commissions for See Already Pretty’s disclosure statement for more details.

Originally posted 2010-11-29 06:00:00.

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26 Responses to “Reader Request: How to Find Your Perfect Boots”

  1. Jess

    First-ever comment to plug Duo Boots ( – a British company but they say they ship internationally, with a massive range of boots in a variety of calf measurements, to fit those with wider or narrower calves! I have had a couple of pairs of their boots and they were genuinely excellent. They're not cheap but they have pretty decent sales.

  2. ashe mischief

    I love your tip about finding the pair you want and then scouring Amazon for them– Amazon is my great secret when it comes to buying shoes. You can ALWAYS get them cheaper (especially Fluevogs!)

  3. Caroline

    Oh Sal, I'm so glad you did this. At some point can you do one focusing on short boots too? I'm just like your reader, would love to find some really workhorse – wear with everything boots … but probably shorter as they could transition to spring as well.

  4. Anonymous

    For me, the neutral color boot I seek is white or cream with a low to mid heel — nearly impossible to find. Finally found a vintage pair of cream boots that worked. I have no idea why this color would be so difficult to find, especially when they make plenty of cream/bone colored shoes/booties all year round. Yes, I live in California, where the weather is mild but there are 30 million other people California residents that might like a light-colored boot, too!

  5. nestra

    I have a comment about the 'fiscally conservative' portion of the request. I do not buy expensive clothing, for a variety of reasons. Shoes, are another story. I feel like shoes are worth investing in. It is worth paying for a pair of classic shoes that will be comfortable all day, go with a range of outfits, and last for years. I don't own many pairs of shoes, but those I have will last.

    I often have to save for a while to buy a pair that I am interested in, but I find that when I buy cheap shoes they are ususally not worth the small price I pay for them.

    Just my 2 cents.

  6. Denise

    First of all, I'm fascinated by Anonymous's comment: cream boots! I've never even thought of them! And of course they would be fabulous in a place like California.

    I've had good luck at Generally I'm not a fan of online shopping (I know you and I part ways here, Sally) but as a big girl with very big calves, they are the only place I found knee-high boots that fit. I bought a pair five years ago, and they still look great.

    My new brown pair is on the way to me now; I hope they fit as well as the first pair did!

  7. Katie

    I bought these boots a month or so ago. I was randomly in DSW and saw them alongside all the other boots, but they stuck out to me. The shaft was tall, the heel was moderate, the sole was flexible (hey, it's Born's little sister brand, comfy!) and I usually cannot find boots because I'm tall, with most of my height in my legs (the majority of knee high boots look like they are mid-calf boots) and I have very thin legs so most boots make me look like I'm standing in buckets. I gave it the go and tried these on, hoping against hope that the shaft would be tall enough and slender enough.

    They were perfect! I wear them a fair amount of time with jeans, skirts, to formal occasions, casual days out, etc. All around a classic shape with a bit of personality, just what you need in an all purpose boot.

  8. Anonymous

    Thanks for the tips on boots. I'm hunting for a perfect pair now. I will definitely start checking Amazon to see if I can find what I want cheaper. Another tip: Try checking They often have some great deals!

  9. Lisa Q

    Duo for tall boots, yes. They wear like iron. Check the sales after Christmas if you can wait. They don't have to cost two hundred quid apiece. I got navy Ravennas (a very basic flat tall boot) for ninety pounds in the January sales two years ago. They are dead comfortable and absolute staples — I wear them several times a week, fall to spring, and my husband just polished them for me and they're like new boots.

    I can also recommend Dansko's short ankle boot with a stacked high heel, Reegan, unreservedly. It's like 3" of height absolutely free — they're as walkable as regular Danskos, I can wear them through long airport connections, to the zoo, whatever. They work with jeans, they make my legs presentable with a shorter hemline. And they'll accommodate tights, socks, or, if you find yourself in a warm place, bare feet. I don't absolutely love the buckle shape on the detail but I'm not inclined to cavil because they're just so dead useful.

    (Also, WRT the Danskos, they're current. If you try them on and you know they work for you, you can always set an ebay search for them. I don't approve of wasting the shoe store people's time, but I also don't approve of not being able to afford decent boots.)

  10. rachelshoots

    Boot related question for all you stylish ladies: would brown boots look good with colored tights and a casual, black jersey dress? I'm leaning towards brown b/c I like the way it looks with denim, but already own the black dress.

    Also, thanks for the tip about Duo Boots. My calves are 16 inches around.

  11. Anonymous

    I also have an indoor/outdoor job, where jeans are required sometimes, and sometimes nicer gear. Bought a great pair of Timberland boots-flat/riding style. Had them for about a year, and they are terrific! They're on the casual side, but for my botanical gardens job, they dress up pretty well.

  12. spacegeek

    OMG Scarpasa is having a 65% off site wide sale!!! MONDAY2010 is the code. Just tried it on a Chie Mihara pair of shoes I've been stalking, and they went from $340 to $119 with free ship and returns! (No association with Scarpasa, btw, just a devoted shoe-aholoic!)

  13. La Belette Rouge

    I have owned lots of boots( Cole Haan used to be my favorites). Now I am totally sold on Fryes. Best boots ever. Now that I have one pair I need another!

  14. withacapitalz

    i wouldn't necessarily say shopping in person is a must for those who are hard-to-fit. so many online shoe stores offer free shipping AND free return shipping – yes, it can be a bit of a hassle still, but i found my perfect pair of boots online after months of scouring shoe stores – try having small feet AND wide calves, ugh.

    (found them at piperlime, btw)

  15. Limette

    I'm currently trying to find the perfect pair of boots. Just started farming and there's a lot of walking around in dirt. I like my rubber boots but they are hardly attractive. I'm thinking leather riding boots. I can't wear high heels but I'm afraid flat boots will make me look shorter and squatter than I currently am.

  16. Kelly

    My first pair of perfect boots took a lot of searching. I have skinny calves and, I discovered, I am apparently quite picky about the silhouette. I felt that most boots made my foot look like a weird shape, or had details I disliked.

    Anyway, I finally found Franco Sarto and now THIS year, my boot shopping went much easier. Last year I wanted some versatile heeled boots – this year I wanted to find nice flat "riding" boots. I still window shopped around for other brands, but I ended up getting a pair of Franco Sartos again. They are just as perfect as the first pair. I guess the designer's taste and silhouette just mesh really well with mine. Next time I want another pair of boots, I don't know if I'll even bother looking at other brands.

    (P.S. As far as boots go, I've had a lot of luck at Nordstrom Rack, for anyone who is looking to save some cash.)

  17. K.Line

    That's a tall order, once you add fiscal conservatism into the mix. La Canadienne boots are great on all the accounts, but they cost about 300 bucks unless they are on sale. I totally agree with you about cognac being a great, and rich, neutral.

  18. Alterations Needed

    Right on about the cognac brown color! It's fab and does indeed go with everything! I've been on the hunt for the perfect pair of cognac brown boots for what feels like forever.

  19. lisa

    I have four pairs of black leather boots with a flat or very low chunky heel, all with slightly different details: moto-style harness, buckle and stud details, brass antique-style buttons up the back of the calves, and a pair of fleece-lined heavy duty snow boots with good treads. It was one of those cases where once I fell in love with one pair of tall black flat boots and knew that they worked for me, I didn't want to wear out the pair I had and I started looking for variations on the same theme. 😛

  20. Rubiatonta

    I just got my second pair of Duo boots delivered here in the States — these are riding boots, and I'm planning on wearing the heck out of them. (The first pair are more of a "Mrs. Peel from the Avengers" style, with a pointed toe and a bit of a heel. Pretty, but not for wearing all day.)

    Just be sure to read the specific style information and reviews, as there can be a lot of variation in fit from one style to another. And if you've got a question, give them a call. It's well worth the cost of long-distance to talk to someone, and since returns from the US to the UK are a pain, it'll save you lots of trouble in the long run.

  21. Erin

    To hit two things in one post – I just got some Franco Sarto cognac brown booties from Nordstrom's and they are fantastic.

  22. Eliza

    I've never tried Franco Sarto boots, but the booties and sandals I have from them were great. They are surprisingly comfortable, and have lasted 3-4 years of pretty constant wear. I'm particularly happy that this brand seems to minimize my big feet.

    For just looking at boots, I like the Endless site, though they are definitely pretty pricey to actually purchase. I generally like their selection the best though, so it saves trawling through hundreds of ugly boots from other sites.

    Rachelshoots: I wear brown boots with black jersey dresses and colored tights all the time! I like to bring the boot and tights colors back up toward my face with a scarf (either around my neck, or a using a silk scarf tied into a headband) or with a necklace. It pulls the whole look together.

  23. Marie

    Two years ago I spent $100 on a pair of Walking Cradles, and it was worth every penny. They're not necessarily the most stylish, but they're EXTREMELY comfortable – one time I wore them for 36 hours straight, no problem. They're wearing out now because I wear them everywhere. Unfortunately it seems all the nice-looking ankle/knee boots either have high heels, or they're not designed to go under jeans.

  24. Chelsea

    I'm hunting for some flat (or chunky, solid, sturdy heels..I like charging around when I go places or running haha. I bounce over sidewalks!) plain old black boots for a good price! I saw a few on AMIClubwear but the suede over the knee boots always make me think of big uggs, and I'm wary of buying them and shipping back.

    Do you ever feel "too sexy" in boots Sal? I find myself a little self conscious wearing boots, and like I'm drawing quite a bit of attention, negative and positive from both males and females.

  25. Anonymous

    I just discovered Eject boots while I was shopping on Amazon last night. They are amaaaaaazing! And way out of my price range, of course. They kind of remind me of Cydwoq boots, but a little more cyberpunk. I'm starting a fund for them now…