January 24, 2025
How to Style Sneakers with Dresses All Year Long
If there’s one thing we love about current fashion trends, it’s how comfort is finally getting its moment. A few years ago, wearing sneakers with dresses might’ve felt like breaking some unspoken style rule. Now, this style is everywhere — and for good reason.
It’s the perfect mix of laid-back and stylish, giving you an outfit that’s cool, practical and modern. From dressing up for brunch to keeping it casual for errands, sneakers with dresses just work. Let’s talk about how to pull off this combo effortlessly so you can feel confident and comfortable every time you walk out the door.
7 Cute Sneakers To Wear With Dresses
A dress with sneakers is the ultimate duo for looking modern and chic while keeping things comfortable. The trick is finding the right sneakers to match different dress styles.
Here are 7 of our favorite pairings of sneakers and dresses that’ll have you looking effortlessly cool — no matter what your plans are.
1. White Slip-On Sneakers with a Floral Dress
This one had to top our list of spring dresses to wear with tennis shoes. Cute floral dresses that hit just above the knee create a look that balances the clean lines of the sneakers with the softness of the floral print. This pairing is a flawless fit for a relaxed day at the farmer’s market, lunch with friends or soaking up the sun poolside.
Styling Tip: To keep the focus on the dress, consider low-profile sneakers. Toss on a light denim jacket for cooler weather or grab a woven bag to capture those springtime vibes. A few gold accessories, like a small pair of hoops or a cute bracelet, can round out the understated yet elegant look without making it feel overdone.
2. Floral Print Sneakers with an Off-the-Shoulder Dress
Floral doesn’t have to be reserved for the dress! White sneakers have been everyone’s go-to for years, but, in our humble opinion, floral sneakers also deserve their time in the sun. Pairing a cute pair of floral sneakers with an off-the-shoulder dress can be just the thing you need to create a playful look that’s unexpected and fresh. The best part? This combination works just as well for casual daytime plans, like brunch or lunch dates, as it does for more creative style moments.
Styling Tip: To create a more cohesive outfit, choose floral sneakers that match the colors in your dress. Keep the accessories simple — like a small handbag or a lightweight scarf — and let the sneakers add a touch of fun to your style.
3. Leather Lace-Up Sneakers with a Denim Dress
This one is perfect for those cooler, autumn days. When it comes to pairing cute sneakers with dresses, there’s something so effortlessly chic about pairing a denim dress with a pair of leather lace-up kicks. This easy but put-together combination strikes just the right balance between casual and elevated. It’s the kind of outfit that works beautifully for grabbing coffee, meeting up with friends or wandering through your favorite neighborhood spots.
Styling Tip: Go for leather sneakers in neutral shades like cream, white, or tan for that classic vibe. If your dress feels a little loose, consider adding a belt at the waist to give it some shape. A tote bag and a few simple accessories, like chunky earrings or stacked rings, can add just the right finishing touch.
4. Metallic Sneakers with a Black Mini Dress
Who says you can’t wear sneakers with a dress for a night out? A bold pair of metallic tennis shoes paired with a black mini dress is living proof that comfort and style can coexist, even when you’re dressing up. The metallic finish of the shoes adds a bold spark that elevates the overall ensemble without sacrificing simplicity — perfect for hitting the dance floor or heading out to dinner at your favorite place.
Styling Tip: Keep the dress simple to complement the shine of the sneakers. Layer with a cropped jacket or an oversized blazer for extra dimension, and finish with a small clutch and minimalist jewelry to keep the focus on the metallic details.
5. Colorful Sneakers with a Halter Dress
We were all taught the rules about matching colors, but we say embrace the colorful sneaker! If you haven’t rocked colorful sneakers before, a halter dress can be a great place to start. Bold or neon-colored kicks give the clean, flattering lines of the dress a fun and youthful edge. Wear this combo for casual days out, outdoor lunches or when you just want to add a little energy to your everyday style.
Styling Tip: If your dress is multicolored, matching one or two colors in the sneakers to the dress can create a cohesive look. For monochrome dresses, multicolored sneakers will add a pop of energy. Accessories can go either way — keep them simple with a small crossbody bag or delicate jewelry for an understated appearance. Want to go louder? Lean into statement pieces to amplify the outfit!
6. Black Platform Sneakers with a Sequin Dress
We couldn’t make a list of dresses without mentioning sequins! Just be careful, this look can quickly go from bold-chic to loud-clumsy. To keep the look more understated, pair a sequin dress with classic black platform sneakers. This combo balances the sequin’s sparkle with the sneakers' relaxed style. Black sneakers are also great for toning down an otherwise bold accessory, like a statement clutch or oversized blazer.
Styling Tip: When it comes to sneakers that look good with dresses that are meant to take center stage, choose a no-frills design to keep the outfit balanced. Add a structured jacket for extra dimension, and let your accessories — like a cuff bracelet or big earrings — complete your look without overwhelming it.
7. Corduroy Slip-On Sneakers with a Maxi Dress
Tired of wearing maxi dresses with sandals or heels? Swap them out for corduroy sneakers to bring a fresh, unexpected twist to your fit. A maxi dress and sneakers look great together because the distinctive shape and texture of the shoes provide depth, while the silhouette of the maxi dress keeps the outfit balanced and stylish. We love this combo for casual days or outdoor events when you want something different but still effortlessly elegant.
Styling Tip: Neutral-toned corduroy sneakers pair easily with most maxi dresses, but a bold color can add extra personality. Throw on a cropped jacket or a light cardigan, and finish with a crossbody bag and minimal accessories.
Tips for Wearing Dresses With Sneakers
Our advice? Don’t overthink it. Ultimately, styling sneakers with dresses is all about what makes you feel comfortable and confident. The secret is finding the right sneakers that go with dresses and then balancing out the details.
Here are some quick pointers to help you nail the look:
- Sneaker choice: Pick sneakers to wear with dresses that match the feel of your outfit. For example, chunky sneakers are great for dresses with an edgy vibe, while sleeker styles keep things clean and polished.
- Dress length: Short dresses go with pretty much any sneaker style, but for midi or maxi lengths, lighter sneakers ensure your ensemble doesn’t feel too heavy.
- Casual or fancy: Think about the mood you’re going for. Casual vibes? Keep it simple with a short dress with tennis shoes. Dressing up? Choose something clean and minimal.
- Colors and patterns: Stick with neutral sneakers if your dress has a lot going on, or use colorful or patterned sneakers to spice up a simpler dress.
- Adding accessories: Get creative with a jacket, bag, or jewelry to pull everything together. On casual days, go light on accessories. For a night out, add bold pieces to elevate your look.
Wear TOMS. Wear Good.
The sneakers-and-dress trend has officially become the best pairing for those who want comfort without sacrificing style. Whether you’re running errands downtown, enjoying brunch with friends or heading out for a romantic evening, this versatile combo works beautifully for any occasion.
TOMS is on a mission to create high-quality products that look as good as they feel. Not only do we offer premium women’s sneakers designed for all-day comfort, we give 1/3 of our profits to community organizations that drive real change. Now that’s a shoe that feels good!
Shop our women’s shoes today to find the perfect pair.