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.

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. I also shared sizing details for each and these no-show socks from Madewell are my absolute favorite and have been for years. Let’s get into it!

What Sneakers to Wear with Dresses – my 3 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 Veja sneakers. Vejas are made in Brazil and have a very classic, almost old-school look. They have very 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 run a little wider and have at 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 mens!

Since these sneakers are leather, they are immediately a little dressier than most sneakers on the market, making them ideal to style 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 all day. They look just as great with jeans as well.

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.

These Isabel Marant sneakers have been on my wishlist for a while (and I’d style them like I do the Vejas) but gosh, they are pricey!

Sharing my favorite Veja sneaker finds below:

2. Canvas Sneakers

The next sneaker on my list in terms of dressiness are canvas sneakers like Tretorns, Converse Chuck Taylors or espadrilles. This 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 last year, and I can’t wait to start wearing them again soon!

The pair I bought last year is called the Seaside Oxford Espadrille from Tory Burch (I also got a pair from H&M that I wore once–those are pictured below as well). Unfortunately 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. My espadrille sneakers pick for this year are the Silva Espadrille Sneaker by Linea Paolo. This style is not a platform, but I honestly find my platform pair to be an ankle-rolling hazard anyway, so I’m in full support of non-platforms this year. AND they are much cheaper than the Tory Burch pair I got last year.

Espadrille sneakers are a super fun shoe for spring and summer, and they feel a bit more playful and feminine than the Vejas.

Linking my canvas sneaker picks below:

3. Sportier Sneakers

The third style of “fashion” sneakers I own are sportier. I actually have a few different pairs of sportier sneakers, so I’m going to share my top 3 picks.

New Balance 327

First are the New Balance 327s, and unfortunately they are hard to find in stock. They’re made with nylon and suede uppers that feel casual yet still on-trend. I wear them with tennis dresses or really casual t-shirt dresses. While they’re definitely not true athletic sneakers so you wouldn’t wear them for workouts, they are comfortable for lots of walking, making them great for travel and vacation.

I have a few different styles of New Balance sneakers, but the 327s are my favorites. They’re unique in that 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 which makes them feel very chic. I own these in a white + black colorway, but I’m always looking for other colors in stock. Like Vejas, these can be hard to find in stock, so get whatever you can snag!

I always go up 1/2 size in sneakers (compared to loafers and heels) so I own a 7 in these. I ordered these later last year, so strangely I don’t have many photos in these where I’m wearing a dress, but I’ll update this post once I have some this spring.

Nike Waffle Debut

Next are the Nike Waffle Debut sneakers. These were best sellers last year (like the 327s are this year) and you could hardly find them in stock. They’re also on the sporty side, but I wouldn’t work out in them. I wear them with tennis dresses since they are comfortable enough to walk in for a handful of miles. I love the neutral colors and the classic swoosh. Thankfully it’s much easier to find these sneakers in stock these days. I also went up 1/2 size in these.

New Balance 237

Last are the New Balance 237s, not to be confused with the 327s above. These are a wider, chunkier style sneaker. They’re casual, comfortable, and look great with tennis dresses, rompers, and other sporty outfits. The insole is pretty flat (even though the shoe does have some lift), so I don’t walk a lot of miles in these. They’re cute, just not great for your arch. Since these are under $100, I own them in a few different colors. They’re so fun to wear! I went up 1/2 size in these.

My favorite sportier sneakers linked below:

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!

Shop The Post