My Go-To Sneakers to Pair with Dresses & Jumpsuits


Sneakers with dresses and jumpsuits are always a good idea, and that is a hill I will die on! I’m not talking about the white gym sneakers and pantyhose popular among working women in the 1980s, running to and from the office in their shoulder-padded suits, heels tucked away in their purses. These sneakers ARE the outfit. They’re function and style.

From sleek, lightweight sneakers to chunkier soles and patterns, sneakers with dresses and jumpsuits can look so cool that you might consider breaking up with heels for good (or at least changing your FB status to “it’s complicated.”)

For this post, I picked my favorite sneakers: Madewell Kickoff Trainer Sneakers, adidas Superstars, and Cole Haan Margo Lace-Up Leather Sneakers and paired them with two dresses and one jumpsuit to show a few different ways to make this look work.

1. Patterned Sneakers

Dress | Sneakers | Lipliner | Lipstick

I’m a big fan of the Athleta Winona Midi Support Dress. OK, big fan is an understatement. And apparently, others are as well because the dress is on backorder in some colors. The Athleta Santorini Thera Dress is a shorter version, similar cut without the back opening. Since the dress is a solid color, I decided to make a statement with my Madewell Kickoff Trainer Sneakers that have a fun spotted print on a white/olive canvas. They complement the dusty rose of the dress, plus the cotton lining and rubber outsoles are both made of recycled materials. What’s not to love?

Fit: The Athleta Winona Midi Support Dress is TTS (I’m wearing a large). The suggestion for the Madewell Kickoff Trainer Sneakers is to size up, but I found my regular size 8 fit just right. If you have a wider foot, I would consider sizing up.

Shop More Patterned Sneakers

Here are some other patterned sneakers to jazz up your wardrobe. I also recently discovered Akwaaba2Fashion — a Black-owned company based in Athens, Greece — on Etsy that sells some really incredible sneakers for under $100.

2. Leather Sneakers

Dress | Sneakers | Ring | Necklace | Lipliner | Lipstick

This En Saison Animal Print Midi Dress is the dressiest of the bunch, but it still works with my Cole Haan Margo Lace-Up Leather Sneakers. Since the dress makes such a splash, I didn’t want the sneakers to compete. The black of the sneakers picks up the black in dress, pulling it all together. The Cole Haan sneakers are lightweight but don’t let them deceive you, you can put in some serious steps with these bad boys. I wore them all around Europe a few years ago with no complaints. They are a great shoe. I am all about mixing metals, so for jewelry, I wore my David Yurman Petit Albion Ring with Garnet and Diamonds to pick up the red and my Madewell Paperclip Chain Necklace that goes with just about everything.

Fit: The En Saison dress is TTS (I’m wearing a large). If you have broad shoulders you might want to consider sizing up. The Cole Haan Sneakers are TTS (I’m wearing an 8).

Shop More Lovely Leather Sneakers

3. Classic adidas Superstar Sneakers

Jumpsuit | Sneakers | Lipliner | Lipstick

I’m low-key obsessed with this Everlane Japanese GoWeave Essential Jumpsuit. As previously blogged about, it is the perfect piece to take you from day to night. I decided to go with a black and white look and slipped on my adidas Superstar Sneakers. There’s a reason these are so popular; they are a classic, comfy sneaker that is always in style.

Fit: Based on the measurements, I decided to size up to a 12 in the jumpsuit. I like a looser fit, so for me, the 12 works better than my usual 10. I also have broad shoulders, so I have to account for them. I like to go by the measurements — not sizes. The adidas Superstars are TTS (I’m wearing an 8).

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Do sneakers work with dresses? The answer is yes. Yes they do.

x, Meredith