Casual Shoe Basics


Well! The responses to this post about shoe basics made it pretty clear that you lovely folks would like some casual shoe-specific input. Many of you have no need or use for heels, and others pointed out that great-looking casual shoes are FAR more difficult to find than great-looking dressy shoes. So here’s a short list of what I consider to be casual shoe basics, and some brand and style recommendations.

frye vera slouch

Frye Vera Slouch

Ahh, boots. Durable, comfortable, and stylish. Those of you living in hot, humid climes may want to pass on this option, but for anyone dealing with seasons, a great pair of casual boots will serve you well for most of the year. Boots can add polish to just about any casual ensemble in a way that flats or Mary Janes cannot, in my opinion. Opt for a classic, knee-high pair with a walkable (or non-existent) heel in a versatile neutral.



puma flats
Puma Zandy

I believe that ballet flats can transition beautifully from work to weekend, but picking up a casual pair will be beneficial if your non-work looks are quite different from your work looks. In my case, this often means a sporty ballet flat like the Pumas shown above. I don’t dig high-vamp shoe styles like loafers and oxfords, but both can totally work especially if you’re all about jeans for casual wear. And low-vamp moccasins, sporty ballet flats, and flat Mary Janes all get the thumbs up from me.

BRANDS TO EXPLORE: Clarks, Puma, J-41ECCO, Merrell


fashion sneakers
Onitsuka Tiger

For a long time, I believed that sneakers/trainers should be worn in the gym or during exercise ONLY. But times have changed, and sneakers are chic once again. Some folks are wearing actual New Balance or Nike gym shoes with casual outfits, but I prefer the look of what brands have deemed “fashion sneakers.” Non-athletic lace-ups with flat, cushy soles or funky slip-ons work well … just track down something that isn’t meant specifically for running, cross-training, or tennis.

While I would say that the vast majority of women could make good use of casual boots and flats, sneakers are less versatile and may suit a narrower set of tastes.

BRANDS TO EXPLORE: Puma, ConverseSuperga, Steve Madden, Josef Siebel


casual sandals

Born Cammi

Although stylish, comfy sandals made it onto my original list, I’m gonna go ahead and repeat myself. Why? Because sandals are more likely to be uncomfortable than many other shoes styles, and it is ESSENTIAL to find a pair that feel as great as they look. Otherwise, your tootsies will suffer all summer long. And we can’t have that, can we?

BRANDS TO EXPLORE: Born, ECCO, Clarks, Kork-Ease, Naot, Sofft

Again, you won’t find snow boots, athletic shoes, hiking boots, or other activity-specific styles on this list because I’m assuming that if you engage in those activities, those shoes will naturally work their way into your collection. Hope this roundup is helpful!

Top image is a pair of Converse All Stars.

**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 2010-12-20 06:25:30.

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30 Responses to “Casual Shoe Basics”

  1. Diana

    This is a great list, but don’t forget Keens! They are by far one of my favorite brands for casual, sporty flats and sandals.

  2. La Historiadora de Moda

    I would also add Sketchers and Me Too to the list for casual flats. I have worn several pairs of both brands into the ground over the year because they were so comfy and went with everything.

  3. Cynthia

    I like a pair of old-school suede sneakers for casual. I wouldn’t wear my zumba shoes as part of an outfit, but my olive suede Simple sneakers are pretty cool. They’d be cooler if I hadn’t forgotten and worn them to mow the lawn once.

  4. Tiffany

    I like your suggestions for sneaker alternatives. I like comfy shoes that I can skip/jump/run in, even with skirts. My favorite shoe for this is the Converse Light. It is very utilitarian, but doesn’t make my feet look huge (or feel so clunky) when wearing a skirt.

    Of course, my motivation for saying this is that I want them to be more popular so they make more colors, hehe.

  5. Leah

    This list is great for me, as I am someone whose workplace is very casual – I have to wear shoes that I can run and walk in. I can’t wear a nice pair of pumps to work – ever! So this is actually a work week list for me, and then I wear my nice dressy shoes on the weekend.

    I will add Vans and Keds to this list. The humble plimsoll has a lot going for it. I particularly like the Vans low cut slip ons. Comfy, cheap and less clunky than a lace up pair.

  6. Bridget

    Simple Shoes are my favorite. I wear them nearly every day, since I work in a lab and don’t want to put my favorite pretty shoes in danger of bleach/chemical spills.

  7. Diana

    Great list! I usually wear casual (but stylish!) shoes most days as I work in a lab and have a partially on foot commute – i refuse to wear commuting shoes except for rain boots. I do think my shoe and clothing styles align – I would call it smart casual, with an eclectic/artsy flair.
    I’d add clogs to this list – not necessarily just traditional danskos, but clog style mary janes (I have the Dansko sally and it gets a lot of wear) and boots (like your Uggs that you posted yesterday).

  8. Jill

    I heart my Chucks. Chucks and a dress make the cutest and comfiest springtime outfit.

  9. Laila

    I disagree with you about loafers and oxfords being “inelegant and awkward”. I myself own several pairs of each, and I think they pair beautifully with a dress or skirt (if done correctly), as well as jeans. However, I am aware that this is a trend that is intended for younger women.

    But thank you for doing this post. I always appreciate the time and effort you put into your research.

  10. Kyla

    Casual shoes can be difficult to find, so thanks for putting this together! I very much agree with everything on this list, with the exception of the heeled sneakers, which just look silly to me. I have a pair of lovely purple suede converse runners that I love for the ultra-casual look, though. I’m still looking for a pair of comfortable, cute sandals, though. I think that will be my goal for this summer’s shopping!

  11. K-Line

    I wear the same shoes for work and play (with a few exceptions at either end of the spectrum). I really like my new Diesel “runners” – they’re more chic with laces/black leather than runners, but that’s the general style. 9West does a brand called Cloud Nine (or at least they used to). And I really love La Canadienne for boots that span the gamut – heels but also rugged footwear. All of it is excellently well made and the materials are beautiful. Not cheap though… Oh, I have a pair of Franco Sarto flat/ 1 inch boots (not for deep winter, more for transitional seasons) that go with everything from skinnies to wide pants to dresses and skirts. So useful. Not leather. They’re the pull ons which work really well if you have skinny calves. They’re not cheap either (though not crazy expensive) and given the wear they get and their durability, they’re a must have.

  12. Eliza

    I like Keds in the summer. In fact, I ended up wearing the same purple cotton sundress and yellow-green Keds almost every day last summer. I also love flat boots in the winter, particularly ones with laces that I can swap for fun ribbons. I always take more risks with casual shoes, because I’m alright with casual clothing being a bit mismatched, but I want my less casual shoes to go with everything.

  13. Emma at Daily Clothes Fix

    Personally, I’m a converse and boots girl. I did have lots of trainers (“pub shoes”) because I used to live in them but as my style has progressed I wear them less and less. I love a good ballet flat too and I have my eye on a pair of bronze brogues which I am hoping to win on eBay.

    That’s a very long way of saying – great post and I heartily agree.

  14. sarah

    hey, perfect – I just bought a pair of sneaker-style shoes made by Coach yesterday (on major sale, score!), so I am totally in the casual/comfortable shoe mindset. Most of my wardrobe (including shoes) is built around my teaching style – business casual with a goodly dash of eccentricity (bright colours, loud accessories, I’ve even taught in my faux-fur trapper hat before). Most of my shoes are heels. However I’m thirty and I have spinal degeneration from a minor birth defect which was aggravated by years of dance and other sporty activities. So I do need comfortable flat shoes (to me, these = more casual). So, although their cloth exterior means I won’t be able to wear them until spring (well, we do get the occasional run of dry sunny winter days), my coach sneaks are a nice new addition to my wardrobe. I also like brogues and saddle shoes (bonus points for being on-trend these days).

    And I wouldn’t dismiss the loafer just yet. I used to have a pair of hot pink snakeskin-embossed Anne Klein loafers that I wore until the leather finally cracked and broke on the sides. I couldn’t wear those shoes without getting a complement – even guys in my department in Cali noticed and loved those shoes. However, I will add that I am quite tall, so if you’re worried about the height of the vamp shortening legs, I will admit that I know nothing about leg-lengthening or leg-shortening tricks as I’ve never had to consider that issue when dressing. But with the return of the boat shoe and preppy style, I think you’re apt to see a lot more loafers on the horizon; so I wouldn’t rule them out just yet, let’s see if a new interpretation can win you over! =)

    • Leah

      OOh I am with you on the loafer front. I am on the lookout for the perfect penny loafer!

      I love the MJ by Repetto but it’s too spendy. Veering towards a pair that Topshop is offering at the moment – it has a cute bow đŸ™‚

  15. lisa

    Good starter list, Sal! I agree with the commenter who endorsed Keds–I jumped back on the Keds bandwagon last summer and wondered why I’d fallen off it in the first place lol. They’re that comfortable. 9/10 times I’ll spend more money on a flat than a heel, or if I had to choose between two pairs of shoes, I’ll go for the flats. They just get a lot more wear than my heels and it’s nice to have some interesting ones to choose from. Matiko, Pour La Victoire, and Kelsi Dagger are worth checking out for interesting flat sandals and boots.

  16. Kyrstin

    I agree with most of this list, but I think you could have branched out a bit more in the flats category. Maybe it’s just because I consider different things casual, but ballet flats work perfectly with casual jeans and a t-shirt looks. They don’t just need to be sporty to be casual

  17. Leslie M-B

    I’m a huge fan of the Rieker brand–most of my sandals and flats are Rieker, and I find the brand to be both stylish and comfortable. Plus, Rieker shoes last for years, even with frequent wear.

  18. Anne

    I have those red Puma flats, and I LOVE them! I’d also add in Privo (by Clarks) for brands to explore for casual flats. I have a pair of their mary janes and a pair of sandals, and both get a ton of wear. And for sneaker alternatives, I’d also throw in New Balance and Saucony – both make cute sneakers that aren’t meant for working out.

  19. Cynthia Brown

    This is a great list. I will confess to wearing my New Balance (those grey ones that everyone seems to have) with loose fitting jeans on a regular basis. I don’t know if this evolved out of my time living in New York, but I kind of like the look of a sweater/jacket, scarf, and slick sneaks. And boots! Your fantastic array of boot/outfit combinations inspired me, so, while Christmas shopping tonight I bought myself a pair of slightly distressed moto lovelies. Cute and on sale, nothing wrong with that. Now I just need to pair them up with some equally cute ensembles.

  20. Sigi

    I’m sorry, sweetie, but there is NEVER any excuse for wearing a wedge/stacked sneaker! Eww!

  21. Katharine

    @Sigi – Have you seen pictures of Nubby Twiglet wearing her Y3 wedge sneakers? I’d argue they’re working for her.

  22. Amy

    I had back surgery this year, so my days of wearing heels are over. And Cole Haan saved my life! By and large, I’ve found that you get what you pay for when it comes to flats. I have to stand up a lot at work now post-surgery, and Cole Haan’s flats have been great for me. Well worth the high price tag. I also live in my Clarks Privos and a couple different pairs of flat Clarks boots. Boots are tricky for me because alot of the time they have a lug sole and are too heavy for walking (when you have a back injury; any drag on the leg is a problem). Clarks are the only ones I’ve found that are comfortable and not heavy.

    Also, I can’t rave enough about Cushe sneakers. They really are cushy! And much more stylish than the average run-around-town sneaker. The toe box is just wide enough to not cause squishy toes, but they don’t look like elephant feet at all. I bought these a couple months ago, and I wear them all the time. And the vinyl design on the sole is extra-cool!

    These are absolutely worth the $94 when you combine a medical issue with still wanting to be cute!

  23. Elizabeth Anderson

    Hello! I’m a daily fan now… How many shoes/boots/sandals do you own? Do you ever post photos of your closet? I have a lot of shoes (not nearly as many as you I bet) and I am at a loss as to where to put them all and in fact sometimes forget I have certain pairs because they are buried (most stay in their boxes b/c I have cats who love love love to chew leather.)

  24. Hadley

    I am sorry I just don’t believe that sneakers with a heel of any kind are ever acceptable in any situation. They make me cry on the inside.

    • Sal

      Don’t be sorry. You’re entitled to your opinion, just as I’m entitled to mine.

      The advantage to wedge sneakers is that you can wear them with jeans, get a bit of a lift from the wedge, keep your jean hem from dragging on the ground, and the shoes themselves look just like regular sneakers. I’m not overly fond of them on their own, but they have their uses as I pointed out in the body of this post.

  25. Alex

    anyone looking for a comfy pair of sandals that can transition from jeans to skirts to shorts should invest in a pair of Birkenstocks.
    they come in so many different styles, colours, and patterns!
    I have two pair of sandals and one pair of clogs…I pretty much live in them.
    I’ve gotten one blister from them, and that was because they were brand spanking new and I wore them exclusively for a week.