Let’s talk about Reef—the brand that’s nailed the art of making shoes you actually want to wear every day. Whether you’re chasing kids, running errands, or sneaking in a beach weekend, Reef has that perfect mix of comfort, style, and durability that just works for real life.

You probably know them for their classic sandals (and yes, they’re still amazing), but Reef’s lineup goes way beyond that. They’ve got slides, sneakers, and cozy slip-ons that feel like walking on clouds. The secret? Their cushioned footbeds and arch support provide the kind of comfort that makes you wonder why every shoe isn’t made this way. Top-notch quality. Reef shoes are designed to last through busy days, spontaneous adventures, and however many playground trips or grocery runs you can throw at them. Plus, they’re made with eco-friendly materials, which is a win if you’re trying to shop more consciously without sacrificing style.

Style-wise, they keep things effortlessly cool—think laid-back coastal vibes that pair perfectly with jeans, dresses, or your go-to leggings. It’s giving “I’ve got my life together” energy, even when you’re running five minutes late.

Reef has you—and your whole family—covered with footwear this fall. Because comfort and style shouldn’t be a trade-off—they should come standard.

When it comes to dealing with summer heatwaves and jam-packed schedules, the last thing you want to worry about is a high-maintenance look. Luckily, there are tons of comfy summer dresses on the market to create a comfy and polished outfit that’s put together in seconds. The best part? They can also be styled with your comfiest kicks.

Below, we rounded up 17 comfy summer dresses that seamlessly pair with your favorite sneakers. From flowy and forgiving maxis that hide insecurities to printed mini styles that keep sweat at bay, these dresses will be the ones you wear on repeat. With styles all under $30, you can pick up an extra dress (or two) for all kinds of occasions, including errand runs, park picnics and lounging at home. Scroll below to find our Amazon favorites.

17 Casual Dresses That Were Made to Wear With Sneakers

Easy, Everyday Staples

1. Our Favorite: From Trader Joe’s runs to coffee dates, this loose maxi dress will be a comfy go-to for all kinds of errand runs.

2. Loose and Slimming: This floral tank dress has a loose, flared silhouette that skims right over the belly.

3. Soft and Stretchy: With a light-as-air fabric, this sleeveless crewneck sundress feels as comfy as your favorite loungewear.

4. Secret Pockets: This relaxed T-shirt dress checks all the boxes— it’s comfy, stylish and has side pockets.

5. New and Notable: Though it’s new on Amazon, this V-neck mini dress is skyrocketing in popularity. The new release was actually bought  over 2,000 times last month!

Brunch, but Make It Casual

6. Our Favorite: With its eye-catching print, we think this boho-style sundress makes the perfect casual brunch staple.

7. Easy Layers: From denim jackets to breezy button-ups, this multicolor floral sundress can be easily layered over when we hit fall.

8. Flowy and Fabulous: This flowy maxi dress is perfect for when you need to be out of the house in minutes.

9. Boutique-Worthy: Not only does this boutique-style dress have cute ruffle details, it’s also majorly discount right now — up to 54% off.

10. Darling Denim: Go from brunch to an country concert with this adorable denim dress that can easily pair with supportive white sneakers.

Vacation-Mode Activated

11. Our Favorite: Perfect for highlighting your summer tan, this colorful floral maxi can make a golden glow pop.

12. Easy, Breezy: Made for beach vacations, this tropical-inspired dress is both lightweight and breathable.

13. Strapless Perfection: Avoid tan lines with this smocked strapless sundress that also doubles as a swimsuit cover up.

14. European-Looking: Channel Mediterranean vibes with this Euro-style mini dress that looks straight out of a quaint boutique in Greece.

Cool, Casual Office Looks

15. Our Favorite: Perfect for laid-back days at the office, this tiered midi dress combines office-appropriate style and all-day comfort.

16. Must-Have Maxi: This elevated maxi dress can be styled with sneakers for an in-office commute and swapped to heels for a meeting.

17. Pleated Perfection: The A-line skirt on this pleated midi dress makes the figure appear slimmer by drawing the eye downward.

Summer dressing has always been my wild card season. While I stick to a pretty predictable uniform of jeans and neutral tops the rest of the year, something about warm weather makes me reach for bright colors and experimental silhouettes. My 13-year-old daughter has definitely noticed this pattern. “Mom, why do you dress so much weirder in the summer?” she asked recently, eyeing my latest purchase with skepticism.

The latest addition to my admittedly wacky summer wardrobe? Gap’s Mid Rise Easy Horseshoe Jeans in Neon Pink Denim, currently on sale for just $35. But here’s the thing—even my brutally honest teenager gave them the stamp of approval. (This is the same child who wears Nike ankle socks and Birkenstocks like every other 8th grader I haul home from lacrosse practice, but I digress. Somehow her opinion still matters.)

Last weekend I wore them to an outdoor concert, and I’m not even kidding, at least five people stopped me to say they liked my pants or ask where I got them. One friend interrogated me immediately, “Are those Gap Horseshoe jeans?! I’ve had them in my cart all week.” And, in a move that really made my day, a very fashionable woman at a Japanese street fair went out of her way to compliment them while I was traipsing around Montreal. I’m now convinced there’s something about pink pants that just makes people want to be your friend—it’s like wearing a billboard that says “I’m fun and approachable.”

Why the Gap Horseshoe jeans work when others don’t

The magic is in the details. These aren’t your typical baggy jeans that make you look like you’re drowning in fabric. The horizontal darts at the knees and vertical seam up the shin give the wide leg actual shape instead of looking like you’re wearing a denim potato sack. The exaggerated curve creates this effortlessly cool silhouette that somehow works whether you’re 5’10” or, like me, barely scraping 5’2″.

The fit is what Gap calls a “horseshoe jean”—fitted at the waist with that dramatic curved leg that tapers at the ankle. The pull-on pant style means no muffin top struggles or having to lie down to zip them up. They’re comfortable enough to wear from morning coffee runs to late-night dinners without that “I need to change into sweatpants immediately” feeling.

At ankle length, they hit at exactly the right spot for us shorter folks. I’m wearing the XXS regular, and they’re not quite as cropped as they look on the 6-foot models, but they also don’t puddle around my ankles like most “regular” length jeans do. The best part? They come in regular, tall, and petite lengths in sizes from XXS to XXL, so you can actually find your perfect fit.

The fabric situation is on point–and eco-friendly

Made from Gap’s “softest denim ever”—a Tencel blend that feels more like elevated loungewear than traditional denim—they’re light enough for warm summer days but substantial enough that you don’t feel underdressed. They’re part of Gap’s water-saving Washwell program and made with recycled cotton, so you can feel good about the environmental impact too.

Styling is easier than expected

I initially planned to pair them with fitted crop tops to balance the volume, but on a whim I threw on my favorite flowy Free People cropped tee and discovered the perfect artist-chic combination. The relaxed-on-relaxed styling shouldn’t work in theory, but somehow creates this effortlessly cool vibe that looks intentional rather than sloppy.

Honestly, I’m already eyeing the brown cow print version because it’s the summer of Cowboy Carter, and if pink pants make you likeable, cow print might just make you legendary. (Unfortunately those are still $88, but since I know how much I love the fit, I’m tempted to splurge.) They also come in bunch of other colors and patterns which currently range in price from $35-$88.

Sometimes the best pieces aren’t the ones you agonize over—they’re the ones that make getting dressed feel effortless and every day a little more fun.