How to style a dress with sneakers

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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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Comments (17)

  1. Donna says
    Posted September 4, 2017

    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!

  2. Posted September 4, 2017

    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
    http://charmainenyw.com

  3. Posted September 4, 2017

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

  4. Andrea says
    Posted September 4, 2017

    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
      Posted September 4, 2017

      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
      Posted September 4, 2017

      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.

  5. Melissa says
    Posted September 4, 2017

    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
      Posted September 4, 2017

      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? 😋

  6. Sophie says
    Posted September 5, 2017

    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

  7. Melissa says
    Posted September 5, 2017

    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!

  8. Posted September 5, 2017

    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’!

  9. Laura says
    Posted September 5, 2017

    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!!

  10. niki says
    Posted September 7, 2017

    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
      Posted September 8, 2017

      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!

  11. Rachael says
    Posted September 10, 2017

    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
      Posted September 11, 2017

      long sleeve denim shirt!

  12. Kristy says
    Posted September 16, 2017

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