How to style a dress with sneakers

Fall Goals & Plans

At the moment I only own 1 pair of footwear that requires extra effort to put on. It’s these wedge espadrilles that I have worn so much this summer. The rest of my shoes are slip on or slide on. Well, besides my athletic shoes that I wear to the gym.

I keep my outfits simple and easy, and the same rings true for my footwear.

I love wearing dresses because they are so comfortable…and honestly nothing is more uncomfortable than sticking to a surface while sitting in shorts. I feel free, I can move and still play with my kids in dresses, and my favorite way to style them down is to slide on some sneakers.

I didn’t think I could pull off this trend, and actually mentioned that earlier this summer, but after a trunk club appointment with my stylist Ari, she made me wear this outfit so I could see how it looked put together. And I loved it!

So if you want to give this style a shot, here are a few things to keep in mind.

  1. The easiest way to pull this off without looking like you are trying too hard is with a casual dress and very simple jewelry. Think v-neck cotton t-shirt dress, like I’m wearing in these photos, or a simple tank dress. In the fall, look for a sweatshirt dress and throw on some sneakers. I think it’s easier to style a casual dress with sneakers than a floral dress but that can definitely look great as well (I wouldn’t have put this outfit together on my own but I followed the advice of a pro 🙂 )
  2. Don’t wear the same shoes you wear to the gym. Get some slip on’s, like these (budget option), or keep a pair of sneakers in nice shape for these outfits.
  3. Style your hair! Since the outfit conveys a sort of careless and easy vibe, don’t take that to mean you can skip everything else. I mean, you CAN, but I don’t think you’ll get the look you are going for.

For another look wearing the same dress, I threw on a lightweight green jacket (similar) with some older new balance sneakers (similar) I’ve had for a few years.

As far as socks go, I don’t wear them in any of my slip on sneakers. And when I wear my new balance sneakers, I’ll just wear no show socks.

What do you think? Are you a fan of the sneakers + dress style?

Photos shot by Jordan Maunder at The Stockroom at 230.



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Donna says · 09.04.17

Yes! I just purchased an easy tank top style sporty shift by Champion. I love its stretchy comfort & wear it with my Sketchers Go Walks (super comfy.) I plan on throwing on a vest or jacket over it with the cooler Fall weather here in Wisconsin. Love my dresses too!

Charmaine Ng | Architecture & Lifestyle Blog says · 09.04.17

Such a cute minimal outfit! I personally love wearing dresses with sneakers, much more than more “girly” types of shoes. Instantly ups the casual factor, plus it’s a lot more comfortable!

Charmaine Ng | Architecture & Lifestyle Blog

Christen says · 09.04.17

I really like this trend! I’ve been meaning to get some more casual New Balance sneakers to try this out.

Andrea says · 09.04.17

Silly question! Shorts or no shorts under the dress?? I love this trend and have bought several t-shirt dress but I feel naked and terrified of bending over lol… struggling with this!

Rhonda says · 09.04.17

Not silly! I was wondering the same. I have two young boys (5 & 2) and can’t imagine being able to play with them in a dress and keeping modest.

Melissa says · 09.04.17

Slip-shorts!!!! They’re the best invention ever! They’re usually with the shapewear in the lingerie section in the store. Super lightweight and comfy.

Melissa says · 09.04.17

I think sneakers and dresses/skirts is soooooo cute. I have an issue, though. I have big feet. Size 11. I feel like when I try to wear sneakers with anything but boot-cut jeans my feet just look awkwardly gigantic. Anyone else?

Katie says · 09.04.17

Yep…size 10 here and I feel like Sasquatch! I actually have some slip-ons just like Kate is wearing and WOW it’s even worse lol. But they are super comfy and maybe no one notices but me..? Maybe? 😋

Sophie says · 09.05.17

This combination is always such a winner – it’s so comfortable and when you get it right it looks great too. I love the second outfit with the New Balance – and your hair looks lovely as always! x

Sophie | Sophar So Good

Melissa says · 09.05.17

This is a beautiful, easy weekend look! I definitely agree you need to do your hair to keep it looking intentional instead of sloppy. Love your posts!

Sage Mathers says · 09.05.17

Love all the tips and options you gave us. I love the look of wearing a dress with sneakers. It’s so cute and it’s a style I will always wear, even if it isn’t on ‘trend’!

Laura says · 09.05.17

I’m dying to ask your weight/height, but that’s rude. ;-P Love seeing someone else with the same build I have, and rocking it!!

niki says · 09.07.17

What are your favorite brand of no show socks? I can’t find any I like. They all tend to slip down off my heel and it drives me crazy. Help!

Mandi says · 09.08.17

Hue brand at Belk. $7 a pair but so worth it. I wash by hand in the sink to make sure they keep their shape!

Rachael says · 09.10.17

Hi Kate 🙂

I have a question- In the photo with something tied around you waste, is that a jacket or a long sleeve denim shirt?

Kate says · 09.11.17

long sleeve denim shirt!

Kristy says · 09.16.17

Thank you for helping me make a decision on the runners I will pack to wear with my jumper while travelling abroad. Very cool!

Hailey Flynn says · 10.13.17

I love this! Especially the New Balance — nice look! Thanks for sharing … And I’m thrilled I discovered this blog!


Nancy N says · 03.15.18

I LOVE THIS POST! I am transitioning to wearing shoes for comfort rather than focusing on style. I am reading about the barefoot walking shoe movement and have trouble shoes that can optimize on both style and comfort! Plus I want to be able to wear these in my business casual work environment – where I wear lots of dresses. So this is perfect for me!!!

Kris says · 07.28.19

I have been doing this all this year and love it!!