What Sneakers to Wear with Dresses (my 3 go-to pairs and how to style)

One of the biggest fashion trends we’ve seen take over our world in the last few years has been sneakers. They are everywhere. And people are wearing them with everything! Think about how we dressed ten years ago. Sneakers with jeans or dresses were typically seen as frumpy, unfashionable, or just deemed as “practical”, not cute. Now, sneakers seem to be the #1 shoe people are wearing. And I’m all for it (see all of my favorite trendy sneakers in this post).

Since sneakers have made such a comeback, retailers are making lots of cute options that look great with dresses, skirts, and jeans. (Although I still veto running shoes with anything other than workout clothes.) However, I know it can be a little confusing to know which sneakers to wear with which dresses, so that’s what I’m breaking down today.

I have a handful of sneakers that I wear with cute outfits, and I’m going to share which ones I wear with each type of outfit. Sneakers are also my go-to for football games. I also shared sizing details for each, and you should go ahead and order these no-show socks from Amazon since they’re what I wear with every pair of sneakers below. Let’s get into it!

What Sneakers to Wear with Dresses – my three go-to pairs

1. White Leather Sneakers

Since wearing sneakers with dresses can feel a little strange at first, opting for a dressier sneaker makes all the difference. My favorite pair of dressy sneakers are leather Vejas. Vejas are made in Brazil and have a very classic, almost “old-school” look. They have simple coloring and are comfortable right out of the box. The only con with Veja is that they can be hard to find fully stocked, so you have to be flexible in terms of colorway. I have ordered a handful of random color combinations over the years because it’s all they’ve had in stock, and that’s just how it goes.

I have tried a few different styles from Veja over the last few years and have found that the Veja Esplar and Recife are my favorites. The Campo style is very similar to the Esplar but runs a little wider and has a thicker sole. For this reason, I prefer the Esplar for the slightly thinner cut and more feminine look. It’s very difficult to tell the difference, though, so if the Campo is all that’s available, get those! And be sure to look at the women’s styles since they can be easily confused with men’s! They come in European sizes and I’d say to size up if you’re on the fence. I’m a size 6.5 in US sizing and wear a 37 in Vejas.

Since these leather sneakers are immediately a little dressier than most sneakers on the market, they’re ideal for styling with dresses. I love the chic street-style look they provide. And it doesn’t hurt that I’m comfortable walking and chasing a toddler and 1-year-old all day. They look just as great with jeans as well.

If you’ve tried Vejas and they don’t work well on your foot (my assistant has this problem), you may prefer this pair of Steve Madden Momentum sneakers (velcro is in this year), or 100% Leather Everyday Sneakers from Quince for a lace-up option (read my thoughts on Quince in this post).

2. Canvas Sneakers

The next sneaker style on my list are canvas sneakers like Tretorns, Converse Chuck Taylors or espadrilles. Last year I discovered Tretorn sneakers which have been such a great shoe in my closet. They’re affordable, lightweight, and super simple which makes them easy to style. They run true-to-size.

In terms of espadrilles, I found the cutest pair of platform espadrille sneakers a few years ago, and I can’t wait to start wearing them again soon! The pair I bought two years ago is called the Seaside Oxford Espadrille from Tory Burch, but they are mostly sold out this year (and they were a bit pricey, too). So, I’ve been scouring the internet for a good alternative, and I think I hit the jackpot. I just found this pair of Azalia Sneakers from Dolce Vita, and I love the raffia and floral combination. Sure, they may not technically be actual canvas sneakers, but they have the same casual, summery feel. Espadrille sneakers look best with flowy, summery dresses.

3. Sportier Sneakers

The third style of “fashion” sneakers I own is sportier. It’s important to know these sneakers are not actual workout sneakers! You could go on a walk in them, but they’re designed for everyday wear– not fitness. They’re usually made with some blend of nylon, and I find that they’re the most comfortable of all the sneaker styles in this post.

The pair I like the most for this purpose is the New Balance 327. These came out two years ago and getting your hands on them was hard for the first year. Thankfully, they’re easier to find now, and they’ve released some fun color options. I have two pairs – a white and black pair and an all-white pair. They’re unique because they have a flared midsole, which hugs your foot right at the arch to give the shoe a more narrow look. They also have a fun, high-traction lugged bottom, making them feel chic. I always go up 1/2 size in sneakers (compared to loafers and heels), so I own a 7 in these.

When styling dresses with sporty sneakers, I always go for the most casual style of dress in my closet. This often means tennis dresses, cotton t-shirt dresses, or casual shirt dresses. The shoes immediately make the outfit feel laid back, so just make sure that’s what you’re going for when you wear these! I also love them with jeans, skirts, and shorts.

Funny enough, I don’t have any updated photos wearing my New Balance 327s with dresses! I’ll update this post in the spring with some pictures.

Tips for styling sneakers with dresses

Wear the right sneakers.

Skip the running shoes. I mentioned this above, but running shoes are a no-go for anything other than workout clothes in my book. They can work well with a tennis dress or skort, but in general, you’ll want a pair of fashion sneakers for wearing with dresses. I’ll share the best kind of sneakers to wear below.

Balance the proportions.

If your sneakers are chunky and bulky, your dress should be more simple. I always like to have one piece of my outfit “do the talking,” so if it’s the shoes, I opt for a dress with a straightforward silhouette or solid color. If my sneakers are minimalistic and simple (both in shape and color), I pick a dress with more interest. I also consider proportions when choosing the dress length. I often wear mini or midi dresses with sneakers rather than maxi dresses (however, I’m 5’1″, so some midi dresses hit longer on me). I think it looks best when a little bit of the leg or ankle shows.

Tone down the accessories.

Since sneakers automatically make your outfit more casual, opt for casual accessories to finish the look. I don’t wear my dressy purses when I have sneakers on– instead, I go for a practical crossbody or tote bag. I also stick to simple gold jewelry (see my favorite jewelry in this post) and makeup.

Final Thoughts

I think we can all agree that this sneakers trend is a gift to the world. I’m SO grateful that it’s “cool” to wear comfortable shoes with my dresses these days, and I’m going to be doing so until further notice. I’m not a fan of Golden Goose sneakers, but if you have other sneakers you love, please share!

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