The Best Sneakers To Wear With Dresses (& Which Bag To Pair)

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I’m such a sneaker girl. It’s hard not to be, when my daily life involves walking kids to school, from school, to the office, to the grocery store, to…well…everywhere, really. One of my friends once had a day that — in addition to the usual craziness — involved several forgotten backpacks/ballet bags/etc., and required multiple extra trips. Her Fitbit, at the end of the day, had registered almost eight miles.

That’s CRAZY. But I can see how it happens.

The problem with sneakers, I find, is that nothing else is ever quite as comfortable. They ruin me for most other shoes. So instead of trying to find shoes as comfortable as sneakers (Linzi — much luck to you on your quest), I typically go the other way: sneakers with EVERYTHING.

One of my fav combos are sneakers & dresses. Sneakers keep a day dress from being overly precious, and dresses literally dress sneakers up into a nonchalantly cool outfit.

The Best Bag To Pair With Sneakers & Dresses

The best bag to rock with sneakers and dresses? Hands down: Straw. Straw bags perfectly bridge between the casual sneaker and feminine dress.

A good straw bag can easily be carried through most of fall. I usually swap out my straw bag for a leather one around November (the same time I stop wearing bare legs with dresses).

Sneakers with dresses. YASSSS. We've found an outfit combo that's comfy, cute & chic, plus perfect for momming. Heart eyes. Happy feet. (& a straw bag).

Sneakers with dresses. YASSSS. We've found an outfit combo that's comfy, cute & chic, plus perfect for momming. Heart eyes. Happy feet. (& a straw bag).

jacket (s) – more sizes here | dress (4) – more sizes here | bag | sneakers

Here are a few straw bags I’d personally recommend…

 

The 2 Best Sneakers To Wear With Dresses

Here we go….

1. Adidas Superstars

I can’t say enough about these sneakers. Adidas Superstars are insanely comfortable (even without socks), and they work with almost any dress (even a fancier, silky one). They’re just chunky enough that they don’t look old fashioned in this era of Dad Sneaks…yet not so chunky that they’re hard to pull off. Classics, truly.

Sneakers with dresses. YASSSS. We've found an outfit combo that's comfy, cute & chic, plus perfect for momming. Heart eyes. Happy feet. (& a straw bag).Sneakers with dresses. YASSSS. We've found an outfit combo that's comfy, cute & chic, plus perfect for momming. Heart eyes. Happy feet. (& a straw bag).Sneakers with dresses. YASSSS. We've found an outfit combo that's comfy, cute & chic, plus perfect for momming. Heart eyes. Happy feet. (& a straw bag).Sneakers with dresses. YASSSS. We've found an outfit combo that's comfy, cute & chic, plus perfect for momming. Heart eyes. Happy feet. (& a straw bag).Sneakers with dresses. YASSSS. We've found an outfit combo that's comfy, cute & chic, plus perfect for momming. Heart eyes. Happy feet. (& a straw bag).Sneakers with dresses. YASSSS. We've found an outfit combo that's comfy, cute & chic, plus perfect for momming. Heart eyes. Happy feet. (& a straw bag).Sneakers with dresses. YASSSS. We've found an outfit combo that's comfy, cute & chic, plus perfect for momming. Heart eyes. Happy feet. (& a straw bag).

navy dress (xs) – take 25% off with code TME25 | black dress (4) – more sizes herejacket (s) – more sizes here  | bag | sneakers

 

2. Classic Vans Slip-Ons

You can’t beat a pair of checkered Vans for some street cred. And they really do seem to be having a resurgence…until I realize that I’ve never stopped wearing mine. I know I’m not alone in this. My point? Whether or not they’re Having A Moment, classic Vans will always look cool.

NOTE: I bought mine a half-size smaller than normal.

Sneakers with dresses. YASSSS. We've found an outfit combo that's comfy, cute & chic, plus perfect for momming. Heart eyes. Happy feet. (& a straw bag).Sneakers with dresses. YASSSS. We've found an outfit combo that's comfy, cute & chic, plus perfect for momming. Heart eyes. Happy feet. (& a straw bag).Sneakers with dresses. YASSSS. We've found an outfit combo that's comfy, cute & chic, plus perfect for momming. Heart eyes. Happy feet. (& a straw bag).Sneakers with dresses. YASSSS. We've found an outfit combo that's comfy, cute & chic, plus perfect for momming. Heart eyes. Happy feet. (& a straw bag).Sneakers with dresses. YASSSS. We've found an outfit combo that's comfy, cute & chic, plus perfect for momming. Heart eyes. Happy feet. (& a straw bag).Sneakers with dresses. YASSSS. We've found an outfit combo that's comfy, cute & chic, plus perfect for momming. Heart eyes. Happy feet. (& a straw bag).Sneakers with dresses. YASSSS. We've found an outfit combo that's comfy, cute & chic, plus perfect for momming. Heart eyes. Happy feet. (& a straw bag).striped dress (xs) – take 25% off with code TME25!! | black dress (4) – more sizes herejacket (s) – more sizes here  | bag | sneakers

What About Golden Goose Sneakers?

Golden Goose sneaks do look amazing with dresses. I’d be remiss if I left them off the list. If you are lucky enough to have a pair of these $500 sneakers, great. But I have trouble recommending these when the my Adidas and Vans are worn just as often…for a fraction of the cost. That said…if you are dying for a pair (and trust me, I GET IT)…here are a few I’d recommend:

 

 

What are your fav sneakers to wear with dresses?  Anyone else with me on the Adidas and Vans train?

All photos featuring The Carina Dress in navy were shot by Marisa of Redfield Photo. All others were shot by Vafa Photography. As always, you guys are seriously the BEST.  

xo,

S

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About Author

Shana founded The Mom Edit in 2008. She lives with the love of her life (his name's Mike) and their two crazy boys in downtown Philadelphia. She loves a good styling challenge (her engineering side shows eventually), appreciates kindness, and usually picks scotch over wine, sneakers over stilettos, and shorts known as denim-underwear, always.

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8 Comments

  1. have to say my jslides slip-ons from
    Athleta totally dominated my summer as did my Gola’s from jcrew – both were on that ridiculous summer sale 2 months ago for like $50 … so perfect🌟

  2. Is it possible to wear sneakers AND SOCKS with dresses, or is it sockless all the way and anything else a lost cause? My feet are really picky about softness and breathability in closed toe shoes and I actually find most sneakers (definitely Vans for example) uncomfortable without socks. Way less comfortable than sandals. I do have a pair of knit-top Nikes that feel amazing without socks, but they’re not the classic street-style look and I haven’t dared them with dresses yet…

  3. Elizabeth Rafter on

    Love this look! That Reformation dress (really, all Reformation dresses) is/are amazing! It looks so great with the sneakers and I can definitely see it worn much dressier. @keilexandra Vans actually make really good no show socks. And Stance no show socks are really the best. I have to wear socks with sneakers (it’s a weird phobia of mine) and these two brands are really good!

  4. Thanks for the inspiration. Yesterday’s ootd New Balance mules and black dress. Sneakers and dresses can be a perfect outfit, spring, summer and fall.

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