Dresses and sneakers are a one-of-a-kind style formula approved by stylists. They combine the effortless design of kicks with the feminine vibe of a frock without losing elegance. Also, they’re easy to pair and ideal for many social activities, including work, brunch with friends, a day at a theme park, traveling and more.
Whether you have a meeting in a boardroom or a birthday party, sneakers help to tone down a fancy ball gown or add a fun flair to a flowy silhouette. “Wearing a pair of sneakers doesn’t change the way a dress looks unless you’re looking for height leverage,” says fashion stylist Sandra Okerulu.
Sneakers allow you to have comfort while looking trendy in a flirty dress. Whether you opt for a sporty, glittery or a muted design, sneakers will give your dress a respite from the common heels and dress combo. Two stylists break down the do's and don’ts of pairing sneakers with dresses, along with a few top picks to shop.
How to style dresses with sneakers?
There are many ways to style dresses with sneakers, but you need to decide which would be the main attraction and build from there.
"Whether you are wearing a clunkier sneaker like the New Balance 740s or a simpler framed sneaker like the Converse All Star Sneaker, you can work your way up," says fashion stylist Talya Bendel.
"Pick either a tulle or nylon sock, scrunch tube sock or your sock of choice (those are just the more popular ones right now). Based on the sock type, you then pick the dress. Sneakers are most commonly worn with sundresses, sheaths, slip dresses, shifts, shirt dresses and dresses like all of the above," adds Bendel.
However, Okerulu says that you want to be careful with the styles you put together. Shirt dresses, T-shirt dresses and flowy dresses are safe choices because they are easy to pair. Below are some recommendations by the stylists, along with editor-approved picks for you to shop.
Best dresses to wear with sneakers
A flowy dress always pairs well with sneakers, especially when it comes with pockets. This design from Ododos features a lightweight fabric that will keep you cool all day long. Plus, it's a great piece to pair with chunky kicks, loafers or sandals. The top area has a tank design with double-layered straps for extra support, while the bottom skirt offers a feminine take on the classic tank dress, offering flexibility and all-day comfort. I have a skort from Ododos which I've been wearing on repeat this summer, and I know this style will offer the same results.
Talya recommends this dress for summer outings for its effortless design and budget-friendly price point. Okerulu emphasizes that a button-down dress with a pair of Adidas works well. “If you do a denim dress, wear a pair of socks that have fun details,” Okerulu says.
While it’s currently on sale for $40, Gap is running an additional sale of 50% off clearance items — making this just $20!
Bendel recommends this short floral find for its effortless and feminine style. You can wear it with high-top sneakers like Converse or pair it with your favorite chunky kicks. The dress comes with pockets and puffy sleeves for a flirty look. Plus, this one is easy to wear thanks to the button-down silhouette.
Associate editor Shannon Garlin loves this casual dress so much that she owns it in two colors. "Not only is it super comfortable, but it also has a built-in bra, which is my favorite thing about Uniqlo clothing. They really know how to do a built-in bra. Since it's so simple with a chic fitted design, you can really pair it with any shoe. It looks great with white sneakers and gives an effortless, elevated look," she says.
Production associate Audrey Ekman recently reviewed this Halara dress, which won a Travel Gear Award for Best Overall Dress. According to Ekman, this dress checks all her boxes for its asymmetric look, unmatched comfort and effortless design. "When I throw this dress on, my outfit instantly looks like I put way more thought and effort into it than I actually did, earning me compliments from friends and strangers alike," she adds.
Associate editor Kamari Stewart loves this easy style because it has pockets. "I always get compliments on this dress. It’s my favorite dress to wear when I don’t know what to wear but still want to look put together. I wear it to work, to run errands and out on casual daytime dates or outings with friends. It’s sporty enough to wear with sneakers but casual enough to wear with sandals which is exactly what I look for in a summertime staple," she says.
Bendel recommends this shirt dress from Everlane for its relaxed design that pairs well with most sneaker styles. However, Okerulu recommends steering away from moto-styled boots. This dress is roomy, lightweight and easy to button up.
Bendel also suggests this dress from Everlane for its comfortable design that offers a casual and textured aesthetic. The rib knit makes it stretchy and cozy for those days you want to look stylish yet relaxed. Pair this one with slim or chunky sneakers.
This maxi dress has become my spring/summer uniform to run errands, walk in the park in or for when I need to get dressed quickly for work. It's made from cotton and features hidden thread chains to snap and hold your bra straps. The slim silhouette pairs well with low-top sneakers and a pair of sheer socks to elevate the look. This dress is similar to one I own from Splendid, which also shows that sleek cut.
Deals editor Rebecca Brown says this dress is long and it falls 53” from the shoulder, "making it the perfect length for a slim sneaker, like a Samba or Nike LD-1000. I plan to wear this in red with my dusty rose Sambas. I think the color combo of red and a neutral pink is so lovely for summer."
The best sneakers to wear with dresses
I love a classic pair like the retro design from Reebok. This one is a favorite among fashion stylists and editors for its timeless aesthetic, cushioned interior and tread pattern. Aside from delivering all-day comfort, Reebok's classic sneaker maintains a plush interior after miles. You can pair it with most dresses thanks to its versatility. Opt for a white pair of sneakers if you need to create multiple outfit combinations and wear it with colorful dresses.
Rothy's Slip On Sneakers are a Travel Gear Awards winner for Best Shoes For Work. Writer Allie Wise tested these shoes around New York City and claims that they are easy to slip on and off, lightweight and ideal for errands.
“For me, it’s all about efficiency in New York City. Finding shoes that are easy to slip on/off with my busy NYC life is a game changer,” she adds. They are great for walking and add a casual look to a flowy maxi dress.
Bendel and Okerulu recommend the iconic silhouette of the Adidas Samba for everyday wear. But if you want to elevate your style, Okerulu advises opting for a bold hue like these silver kicks.
"These are the perfect pair to wear if you are looking to add a spark to your everyday dresses. Specifically, looking to wear a sneaker that goes well with your evening dress or gown," shares Okerulu.
Both Bendel and Okerulu suggest adding this pair to your footwear arsenal for a casual fit. This one goes well with a tennis dress or exercise dress since the design combines old-school vibes. It has a low profile with a lightweight build that pairs well with a maxi or short dress. The design pays homage to a nostalgic era when crop tops, baby dolls and low-rise jeans reigned supreme.
Stewart has been a fan of these travel-friendly kicks for their comfortable, convenient and stylish design — "a three-peat that’s not easy to achieve with sneakers most of the time."
"They truly are hands-free and I love just being able to slip them on and off at a moment’s notice. I also love that the Monarch style is a little dressier, so I can wear it with actual dresses, to the office or just casually with jeans or shorts. They’re comfortable enough to wear all day, so I like to wear them when I know I have to dress up a bit more, but know that I’ll be on my feet for a while. I even wore them to my own engagement!" she quips!
I have this pair in the light gold hue, and it has become my go-to shoe for traveling and everyday wear. They're easy to put on and match with casual looks. The footbed is comfortable, the construction flexible and the design is elegant. The first time I washed them, it took me about three days to dry, but the final results looked great. They were easily cleaned and remained soft afterwards. It comes with two types of laces that you can mix and match as well. But I left them with the satin laces in because they're more comfortable and prettier.
Frequently Asked Questions
According to Bendel, you want to avoid clunky jewelry and opt for simplicity. "Unless you like a necklace stack of thin chains with delicate pendants or even a thin ribbon choker. I would also avoid belts. They aren’t really necessary with the dresses listed and the juxtaposition of sneaker to belt is rarely a smooth combo," says Bendel.
Another thing to keep in mind is the dress length. If you are going to wear a long dress, "don’t wear a sneaker with gems or beads or things the dress can snag on. On that same note, you don’t want the dress to hide the sneaker if it has beautiful details," shares Bendel.
"You can wear a formal dress with a sneaker though it’s not common. A good example of where you may see this is at a wedding where the bride gets into her last look of the night, usually the party look and can sometimes opt for glitzy sneakers," says Bendel.
As for Okerulu, she doesn't shy away from a ball gown and a pair of sneakers. "It allows the dress to be seen while still wearing a pair of sneakers. But, you want to wear something slim and sleek like Adidas, Nike or New Balance," shares Okerulu.
While Bendel is not big on do's and dont's, she suggests leaning more toward complimentary tones as a style rule. "For example, neutrals with neutrals, gem tones with gem tones even neon with neon. If you are going to mix prints, don’t wear abstract for both sneaker and dress; do one or the other and definitely don’t do busy print on busy print," she adds.
How we chose
We selected these products based on insights and recommendations from two fashion stylists and approved picks from Shop TODAY editors and staffers.
Jannely Espinal has been with the Shop TODAY team for over three years and has covered a variety of topics with a focus on fashion and footwear.
Meet the experts
- Talya Bendel is a New Jersey and New York City-based fashion stylist and 3-times New York Times best-dressed. She is also a film stylist, bridal and costume designer whose work has been featured on Netflix, Women’s Wear Daily and Warner Brothers.
- Sandra Okerulu is an accomplished celebrity style expert who has styled some of the biggest names across the world.
