The Best Sneakers to Wear With Dresses & Styling Tips

I’m back today with another styling installment! While this topic might not be for everyone, I’m eager to chat about wearing dresses with sneakers. I briefly touched on this pairing when I shared Adidas Gazelle outfit ideas, but today we are digging deeper! I’m going to chat about my current favorite sneakers to wear with dresses, styling tips and tricks, outfit ideas, and why I love experimenting when it comes to fashion. Who knows, by the end of this post, you might just find yourself tempted to try out this unexpected combination, if you haven’t done so already!

Why I Love This Pairing

Experimenting is one of the things I LOVE about fashion. Do you know what else I love? A unique juxtaposition. For example, wearing a designer dress with a great pair of Amazon fisherman sandals or pairing casual jean shorts with a dressy button-down shirt. This same element of surprise can be accomplished by accessorizing a dress with sneakers. And in my opinion, it just “works”. For me, what it comes down to is fashion is meant to be fun. So, taking risks and trying new things is a great way to find your personal style!

How to Choose the Right Sneakers to Wear with Dresses

As always, when it comes to styling, there is no right or wrong way! However, after playing around with this casual and elevated pairing, I’ve noted what does and doesn’t work for me. Here are three tips for finding the best sneakers to wear with dresses.

1. Think About Proportion

I find a dress and sneaker combo works best when the dress is between mini and midi length. Wearing sneakers with tea length or maxi length dresses can be tough. In my opinion, this pairing feels the most balanced when you are showing a little bit of leg!

2. Don’t Create a Busy Look

I typically love print on print. But, when it comes to wearing sneakers with a dress, I try to keep either the shoe or the dress fairly straightforward. Since I am already blending casual and dressy, adding multiple prints into the mix feels a bit too busy. I tend to reach for a simple, solid-colored pair of sneakers to wear with a dress that is printed or more detailed. On the other hand, when I want to wear a multi-colored or printed shoe, I normally choose a solid-colored dress.

3. Keep the Accessories Casual

Combining sneakers with a dress gives off a casual, everyday feel. Therefore, I think it’s best to keep the accessories casual as well. Elegant earrings or overly fussy bags can add confusion to the whole look. Instead, I recommend reaching for a great crossbody, a casual top handle purse, or a simple tote bag. I’m not opposed to adding statement jewelry to the outfit, but I do try to ensure the pieces aren’t too dressy.

My Favorite Sneakers to Wear With Dresses

Okay, now let’s talk about my favorite sneakers to wear with dresses. I have become a bit of a sneaker lover lately, so I have four great ones to touch on today. In addition to wearing them with dresses, these shoes are also perfect to throw on with jean shorts for a casual summer look!

1. Veja Sneakers

If you’re looking for a simple and versatile pair of sneakers to wear with a dress, these might be the ones for you. I started wearing Veja sneakers way back in 2017, as seen here. I love that they can be worn in so many different ways. Over the years, I’ve dressed them up with dresses and dressed them down with my favorite work out gear.

I find Veja shoes to be very comfortable, high-quality, and fit TTS. I have owned five pairs and all have held up amazingly well. While the pairs I own are minimal, they also have some very cool novelty options such as this rainbow pair and this bright pair!

2. Adidas Gazelle

These shoes are such a workhorse in my closet that I wrote a full post featuring Adidas Gazelle outfit ideas! They are a classic sneaker that looks incredible with so many dress shapes, colors, and prints. I tend to stick to white stripes in my Gazelles, but they do come in a ton of fun color options. These sneakers fit TTS, and you can comfortably wear them all day long!

3. Tretorn Shoes

Tretorn shoes are made of canvas, so they are super pliable and also washable! These feel uber casual, and I love the retro look they add to any outfit. I also love that at $75 or less, they are an amazing quality for the price. Not only are these great sneakers to wear with dresses, but I’ve also been spotted styling them with a favorite pair of denim, a casual terry cloth shorts set, and so many other outfits. Also don’t miss these fun gingham Tretorns!

4. New Balance 754

I really love all New Balance, but the 754 are my favorites! Of all the sneakers on this list, these feel the most “athletic”, making them a bit trickier to style. Personally, I stick to mini dresses and knee-length dresses when wearing these. I also opt to keep the accessories a bit more minimal and casual.

How to Style Sneakers With Dresses

Putting together outfits is something I look forward to each day. It’s just so much fun! Therefore, I couldn’t wrap this up without sharing a few different ways that I’m currently wearing sneakers with a dress. In reality, there are too many great possibilities to name, but these combos are the ones really tickling my fancy right now!

A Printed Mini + Casual Sneakers

Minis are having a moment, and there are so many good options right now. If you love a colorful printed dress as much as I do, this tropical mini dress (from one of my favorite brands) would look great paired with these green sneakers. These shoes would look equally as chic with this retro print mini shift. Both pairings would bring an unexpected, but awesome, mix of casual and dressy. I recommend completing both of these outfits with this fish wicker clutch that I own, love, and always get lots of questions about!

A Striped Midi + Canvas Sneakers

Stripes are so easy to mix and match. Maybe this is why I have so many in my closet! While this smocked striped dress is on the longer side, it would totally show enough ankle to wear it with a sneaker. This dress would look great with these red Tretorn sneakers, these $11 retro sunnies, and this woven red tote from Amazon. Looking for more striped dresses to wear with sneakers? This one, this one, and this one are all beautiful options as well!

An Easy Knit Dress + Classic Sneakers

Sometimes simple is best. A great, form-fitting knit dress and a classic sneaker make for the perfect casual look. To create a bit of interest, you could add a cropped trench coat or cinch the waist with a timeless sweater.

Classic Sneakers to Wear With Dresses

So what do you think? Have I convinced you to test out some dress and sneaker combos? Were you already a fan of this surprising pairing? Or do you plan to stick with wearing dresses with sandals and heels? Either way is okay! I’m always an advocate for “to each their own” when it comes to fashion! For more styling ideas, check out my posts on how to style wide-leg jeans, turtleneck outfit ideas, how to style a midi skirt, and Adidas Gazelle outfit ideas.