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How to wear a dress with sneakers

Jul 8, 2019

Dress: Madewell (available at Nordstrom and Madewell but is on sale at Madewell!) Runs TTS! This print also comes in a Midi dress version as well as a top and midi skirt! Sneakers: Tretorn (run TTS) Purse: Amazon! Best find ever! Not the best quality but duh, it’s $15 ?White Jean Jacket: old, but love this Topshop version

Happy Monday!

We have a BU-SY week ahead of us coming off the long holiday weekend. It was so much fun to unwind at the lake and spend a lot of time in the sun with family! Hitting the ground running this week though, are you ready for this agenda? (Pray for me.) 

Tomorrow is my 31st birthday, and also the huge launch of Beautycounter’s Countertime “Retinatural” collection–AKA their clean version of retinol! I’ve been testing it out over the past few weeks and I think you guys are going to LOVE IT. If you’ve been looking for a clean anti-aging line, this is it!

Tomorrow night we’re going to early dinner and then Les Miserables opening night! I’m SO EXCITED! It’s my favorite musical and I’ve never seen it on Broadway!

Wednesday at 6am we leave for California for my BFF Kai’s wedding! (Remember her? She’s the one that owns the awesome catering company, Littlevent!) 

Amidst the wedding festivities, the Nordstrom Sale launches on Fridayso I’m hoping to get to a nearby Nordstrom in San Diego to test drive some favorites to share with you guys, so I will be working around the clock with that in between bridesmaid duties!

I’m honestly exhausted just writing this–but busy is a good thing! All amazing things coming up! ?

Anyway–let’s jump into today’s blog post!

Today’s topic: styling dresses with sneakers! 

Wearing sneakers with dresses is something I once thought “wasn’t for me”–it was a combination that felt “too tomboyish” or “too trendy” and often times “too frumpy”–what was I doing wrong? Why couldn’t I make it look good? 

Then I discovered the staple that is the classic, white sneaker, and I realized that I had just been pairing the WRONG dresses with the WRONG sneakers all along. Turns out, it’s an adorable combination that ANYONE can pull off! Today, I’m sharing a few tips if you’re also needing a bit of sneaker + dress inspo as well! 

How To Wear A Dress With Sneakers

My biggest piece of advice: Remember the Juxtaposition Rule. 

How To Wear A Dress With Sneakers

If you haven’t read this blog post on the Juxtaposition Rule, it basically breaks down the #1 most important style rule that exists, at least in my book. Once you figure this out–putting outfits together will come FAR more natural to you. 

Essentially, it’s the idea of mixing together differing styles to result in a visually interesting outfit. The kind of outfit that you can’t quite put your finger on why you like it so much–it’s by no means loud or over the top (granted, you’re welcome to make it that way, if that’s your thing) but when I do this–it’s classic, but with a twist.

Think of it this way–to make a great cocktail, you need contrasting ingredients, right? To create the ideal balance, you need the right amount of sweet to sour–too much of one thing, and it’s either boring, or downright undrinkable! The same goes with clothes. 

So, let’s relate the Juxtapositon rule back to the task at hand: styling sneakers with dresses. Here are some tips that will help: 

How To Wear A Dress With Sneakers by Jess Keys

Show some leg:

This is the easiest rule to follow. One of the biggest complaints I get from my ladies who try and fail at styling sneakers with dresses is, “I just feel frumpy!” To that my first answer is, “you’re probably wearing the wrong sneakers” and the second is–go with shorter hemline–like the one on this dress! 

Let’s go back to the cocktail reference again. If your outfit is a margarita, your hemline is JUST the right amount of tequila. The amount of skin you’re showing is the tequila–a little leg creates the perfect balance. Too much leg and your drink is too strong (and your Grandma will tell you that you look like a lady of the night). You feel me? 

Feminine details:

Little details like ruffles or tiny, feminine floral print contrast nicely with more tomboyish sneakers for the perfect happy medium between the two. Cocktail, remember? Feminine vs. Boyish creates the right amount of balance!

The dress I’m wearing here: 

Love this little Madewell number (available at Nordstrom and Madewell but is on sale at Madewell!) As you’ll notice, it happens to hit on both of the “leg” and “feminine” rules at play here–but can you just go with one or the other? Absolutely! A feminine midi dress (this one comes in midi version!) would also look just as lovely as a dress with a shorter hemline. 

I love this dress for so many reasons–the wrap silhouette is always one of the most flattering necklines around. It pulls the eye downward and nips in at the waist–emphasizing your figure! I also love the sweet print and button details! All in all, it’s a dress that’ll look just as cute with sneakers as it will with flats, sneakers, heels, and even booties when the weather starts changing! 

white jacket and red dress outfit

The perfect sneaker to pair with dresses: 

OKAY–here is where people often get into trouble–pairing the wrong dresses with the wrong sneakers. What you want to look for is a classic, crisp, white sneaker. The right sneaker is a blank canvas and chameleon–they can be preppy, feminine, edgy, fashion-forward, and classic all at once. Here are my two favorite pairs: 

Tretorn Sneakers: You’ve likely seen me wear these shoes A LOT unless this is your first visit here (in that case, WELCOME!) but I basically haven’t shut up about the canvas Tretorn sneakers since I bought them earlier this winter. They are so comfortable, require ZERO break-in, and they go with everything. They’re a little preppy, a little retro, but 100% classic. 

Jack Purcells: These are what my Tretorns replaced–I had worn them into the ground, on multiple European adventures, and they were my white sneaker of choice for many years. I love them as well! I will say if you’re debating between the two, I think they’re both fantastic style-wise, but Jack Purcells do require some break-in, just as a heads up. 

red floral dress

But Jess–what about..? 

Allbirds: I get this question a lot, and I LOVE my Allbirds. (I have two pairs!) Can you wear your Allbirds with dresses? YES–but–it’s very hard to find the right dress to wear with Allbirds. The dresses that go with Allbirds are going to be your very basic cotton t-shirt dresses, like this one from Everlane! I don’t think they will ever look good with a feminine dress. 

Everlane Tread sneakers: I also get asked which white sneakers are my favorite between my Tretorns and my Everlane Tread sneakers–and I can’t choose a favorite! I love them both SO much and I wear them with different things. Like Allbirds, they are too sporty/chunky looking to go with feminine dresses for me–I say this because they definitely WOULD but that’s one of those ugly fashiony things that isn’t my style. Cool for some people, not for me personally. That being said, I still wear my Tread sneakers ALL the time and I cannot sing their praises enough! But if you do want to style them with a dress, again, like the Allbirds, go with something very minimal and casual–otherwise it looks a little “try hard” in my opinion. 

red dress with white sneakers

Hope you have a wonderful start to your week! 

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