Cute flip flops to wear with summer dresses are the secret weapon of effortless summer style. The days are longer, the weather is warmer, and your collection of breezy dresses is calling your name. It’s the season where comfort and chic go hand-in-hand. But as you pull out that favorite floral maxi or that easy cotton sundress, one question always pops up: what shoes do I wear?
For years, the answer might have been a delicate sandal or wedge. But I’m here to tell you—the humble flip flop has made a major comeback. Today’s designs are stylish, supportive, and made to complement your summer outfits, not clash with them. Finding the right pair isn’t just about what’s easy to slip on—it’s about elevating your look from casual to coolly intentional. And these flip flops are ready for their moment in the sun.
🩱 Flip Flops That Pair Perfectly with Dresses
Ready to find your perfect match? Below are 21 flip flops that prove you don’t have to choose between comfort and style. From beachy basics to blinged-out beauties, these picks are made to complement your summer dresses—whether you’re strolling through a resort, heading to brunch, or dancing the night away in a breezy maxi. Let’s dive into the cutest, comfiest, and most dress-friendly flip flops of the season.
🩷 1. DREAM PAIRS Women’s Arch Support Flip Flops
Best for: All-day comfort with casual cotton or flowy midi dresses
These cute flip flops to wear with summer dresses strike the perfect balance between laid-back style and real support. With a soft cushioned midsole, deep heel cup, and mild arch support, they’re ideal for walking-filled days or casual brunch dates. The textured insole adds grip—so no slipping at the pool or boardwalk—and the sleek thong design complements everything from floral sundresses to linen skirt sets. Lightweight and durable, they pack well, wear well, and keep your feet happy from morning strolls to sunset cocktails.
🌊 2. OOFOS OOriginal Sport Recovery Sandal
Best for: Post-walk recovery or sporty pairings with tank dresses or rompers
Comfort first—but make it stylish. These OOFOS recovery sandals aren’t your average flip flops. Designed with proprietary OOfoam that absorbs 37% more impact than traditional soles, they’re a game-changer for tired feet. The sleek, modern silhouette pairs surprisingly well with simple cotton dresses or athleisure-inspired outfits, making them a hidden gem in the world of flip flops that go with dresses. Backed by science and approved by podiatrists, they’re ideal if you want that “walking-on-clouds” feel while still looking polished enough for casual outings.
🏝️ 3. OLUKAI Ohana Women’s Flip Flops
Best for: Beachy maxi dresses and tropical resort wear
These beachy-chic flip flops were practically made for summer dresses. With water-resistant straps, a quick-dry lining, and a high-traction rubber outsole, they’re perfect for coastal vacations, poolside lounging, or exploring beach towns. What makes them stand out? The fit. They offer generous arch support and a true-to-size, wide-foot-friendly design. Slip them on with a strappy sundress or printed maxi and head to dinner straight from the beach. If you’re looking for dressy flip flops for casual wear that can keep up with adventure, the Ohana delivers.
🌼 4. Teva Women’s Mush II Flip Flop
Best for: Boho skirts, tiered dresses, and laid-back vibes
Boho meets comfort in the Teva Mush II, a cult-favorite flip flop that forms to your foot and styles effortlessly with flowy dresses and weekend fits. The soft, yoga-mat-inspired footbed cushions every step, while the vibrant, woven straps add a playful pop to your outfit. Ideal for travel days, farmers’ markets, or just lounging in the garden, these flip flops are light, easy, and made to move. They’re a go-to choice for anyone who wants flip flops that pair with summer dresses—and actually feel good after hours of wear.
✨ 5. Crocs Unisex Crocband Flip Flop
Best for: Athleisure dresses, sporty sundresses, and beach days
Don’t sleep on Crocs. This Crocband version brings their signature comfort to a minimalist flip flop style—perfect for casual dresses, swim cover-ups, or tennis-inspired fits. The Croslite foam offers that springy, walkable support Crocs are known for, while the striped sole adds just enough flair to keep things cute. Lightweight, easy to clean, and surprisingly flattering with simpler dress silhouettes, these are some of the most versatile summer flip flops you can pack. Bonus: they’re great for travel and quick changes between pool and patio.
💫 6. Volcom Forever and Ever Flip Flop Sandal
Best for: Edgy-chic outfits and casual jersey dresses
If you love mixing soft and structured, these cute flip flops for dresses are your vibe. The braided synthetic leather strap gives off a sleek, slightly edgy look—perfect for dressing up a simple tee dress or fitted ribbed tank dress. Molded arch support and a Recliner Comfort Foam footbed make them more than just a pretty pair, though. They’re comfy enough for everyday errands or concerts in the park, and stylish enough to wear with your favorite crossbody bag and oversized sunnies.
🎨 7. ChayChax Women’s Two-Tone Flip Flops
Best for: Colorful summer dresses, bold prints, and travel outfits
These playful, two-tone flip flops are ideal if you love wearing bright sundresses or patterned summer sets. Lightweight with soft EVA cushioning, they offer subtle arch support while keeping things fashion-forward. The contrast straps add a little pop without being too loud, making them a great companion for bold summer dresses that need a neutral but interesting shoe. Whether you’re poolside, shopping local markets, or grabbing iced coffee in a cute shift dress, these flip flops have your back.
☀️ 8. Skechers Women’s On-The-Go 600 Sunny Flip Flop
Best for: All-day walking in cute midi or tank dresses
Comfort queens, this one’s for you. With 5Gen cushioning and a Goga Mat footbed, the Skechers On-The-Go flip flops are made to walk all day while still looking cute. The soft mesh straps add a sporty flair, but the minimalist shape keeps them feminine enough to wear with ribbed knit dresses or T-shirt dresses. They’re machine washable, ultra-breathable, and slip on effortlessly—great for travel days, boardwalk strolls, or exploring new towns in style and comfort.
🌬️ 9. Clarks Women’s Sea Breeze Flip Flop
Best for: Breezy linen dresses, beachy cover-ups, and minimalist outfits
These are the understated flip flops that go with everything. The Sea Breeze sandals from Clarks are soft, lightweight, and built with the brand’s Cloudsteppers comfort tech. With a cushioned EVA footbed and gentle fabric upper, they’re irritation-free and perfect for warm, humid days. Their classic shape makes them easy to style with neutral-toned dresses or beachwear, and they provide a little extra heel lift without losing that relaxed vibe. Think: brunch after the beach, or running errands in your favorite tiered midi.
🌸 10. KuaiLu Women’s Arch Support Flip Flops
Best for: Dressy-casual looks, vacation outfits, and longer walks
These floral-strapped flip flops bring style and serious support. Designed with a cushioned yoga mat footbed and structured arch, the KuaiLu sandals make walking feel effortless—even when you’re in a maxi dress or dressed-up summer romper. The floral print adds just enough elegance to elevate a simple outfit, making them ideal for cruise dinners, sightseeing in sundresses, or summer weddings with beachy dress codes. If you need supportive flip flops that go with dresses, these are a standout choice.
🌺 11. Havaianas Women’s Core Flip Flops
Best for: Minimalist sundresses, retro styles, and casual beachwear
Sometimes simplicity is the ultimate statement. These iconic Brazilian flip flops are made from soft, premium rubber with a rice-pattern sole for grip and a slim silhouette that flatters the foot. They’re super lightweight and keep their shape wear after wear. Pair them with a halter dress, vintage skirt set, or that cute cover-up you always pack for vacation. If you’re looking for cute flip flops to wear with summer dresses that won’t distract from your look, Havaianas are a timeless choice.
🌿 12. Cobian Women’s Braided Bounce Flip Flops
Best for: Flowy maxi dresses and dressier day-to-night outfits
With a braided faux-leather strap and metal detailing, these flip flops bring an elevated feel to any outfit. The extra thick, bouncy foam footbed and built-in arch support keep them comfortable all day, while the neutral tones and slim profile make them easy to dress up or down. They pair beautifully with everything from boho wrap dresses to soft floral maxis. For a flip flop that looks as good as it feels, the Cobian Braided Bounce checks every box.
🐚 13. Rocket Dog Women’s Spotlight Flip Flops
Best for: Coastal looks, beach parties, and flowy sundresses
If fun and casual is your summer style, Rocket Dog delivers. The Spotlight flip flops feature wide, soft fabric straps with a trendy edge, set on a cushy foam footbed that makes them easy to wear all day. They’re great with simple tank dresses or spaghetti strap styles, adding a little personality without going over the top. These are the beach flip flops for women who want comfort and flair wrapped into one sunny-day staple.
🌸 14. Floopi Flip Flops for Women
Best for: Romantic prints, travel outfits, and resort wear
From florals to sporty knits, these Floopi flip flops come in styles to match every kind of summer dress. Their yoga-mat-inspired footbed offers arch support and a springy feel underfoot, while the toe post is soft and non-irritating. They’re lightweight, easy to wash, and packable—ideal for beach trips or sightseeing days. If your wardrobe leans into bright colors, soft fabrics, and versatile pieces, these flip flops will fit right in with your summer style lineup.
🧘 15. REEF Spring Woven Women’s Flip Flops
Best for: Eco-conscious style, beach dresses, and effortless layering
Made from recycled materials and designed for all-day wear, these Reef flip flops are as comfortable as they are conscious. The anatomical arch support, wide shape, and soft straps keep your feet feeling fresh, while the woven design adds texture that looks great with boho maxis or tiered sundresses. No break-in needed, no slipping on wet surfaces—just stylish, sustainable comfort. For women who want flip flops that go with dresses and do good for the planet, this pair is a must.
🧘♀️ 16. Sanuk Yoga Joy Flip Flops
Best for: Relaxed travel looks, minimalist outfits, and everyday wear
The Sanuk Yoga Joy lives up to its name—with a yoga mat footbed that molds to your foot and synthetic leather straps that keep things classy. They’re slim, sleek, and pair beautifully with casual knit dresses or beach cover-ups. Plus, they’re made with recycled materials, so you can feel good wearing them on the move. If you’re looking for flip flops to wear with summer dresses that don’t scream “sporty,” this pair is simple, sustainable, and surprisingly stylish.
💖 17. Yellow Box Women’s Feliks Flip Flops
Best for: Flirty sundresses, date nights, and brunch with the girls
These glittery stunners are proof that flip flops can sparkle—literally. The Yellow Box Feliks flip flops feature dazzling straps that instantly dress up your look while the lightweight EVA foam sole keeps things comfy underfoot. Pair them with a bold print mini dress or a romantic maxi, and you’ve got a go-anywhere outfit that feels elevated without trying too hard. If you’re after blingy flip flops to wear with summer dresses, this pair is your secret style weapon.
✨ 18. Flojos Women’s Fiesta Flip Flops
Best for: Flowy boho dresses, resort wear, and everyday glam
These slim, sleek flip flops bring just the right amount of sparkle without going over the top. With a soft faux leather strap, cushy EVA footbed, and subtle arch support, the Flojos Fiesta blends beauty with comfort. Ideal for beach walks, outdoor lunches, or dressing up a simple sundress, they’re lightweight, versatile, and totally chic. Think of them as your go-to glam-meets-casual sandals for summer 2025.
👑 19. Skechers Women’s Vinyasa Lotus Princess Sandals
Best for: Neutral-tone dresses, cruise dinners, and day-to-night looks
A name like Lotus Princess says it all. These Skechers bling flip flops feature yoga foam comfort paired with embellished straps that add an elegant shimmer to any look. The flexible sole moves with you, while the rhinestone details sparkle under sunlight or city lights. They’re perfect for styling with light neutral dresses or even palazzo pants for an upscale casual vibe. Beauty + comfort = royalty-approved.
🌟 20. Yellow Box Women’s Africa Flip Flops
Best for: Flowy maxis, chic resort sets, and tropical nights out
If you love a little lift, the Yellow Box Africa flip flops bring bling and a subtle wedge heel for a more elevated profile. The embellished strap adds just enough glam, while the footbed logo detail gives it a boutique feel. These look amazing with strapless dresses, beachy caftans, or even a solid tank dress when you want the shoes to do the talking. Sparkly and versatile, they’re a summer-night essential.
🪩 21. Crocs Women’s Platform Flip Flop Sandal
Best for: Street style with flair, sporty dresses, and festival fits
Crocs goes glam with this 1.6-inch platform flip flop that brings both height and comfort. If your summer vibe is edgy-chic, these are the statement flip flops you didn’t know you needed. The platform sole makes your legs look longer under a mini dress, while the clean design works great with crop tops and skirts. Bonus: they’re lightweight, customizable with Jibbitz charms, and festival-friendly.
📊 At A Glance Table: Flip Flops to Pair with Dresses
| Flip Flop | Best For | Comfort Features | Style Match | Price |
|---|---|---|---|---|
DREAM PAIRS | All-day wear | Deep heel cup, cushioned sole | Flowy midi dresses | $25 – $35 |
OOFOS | Recovery & errands | OOfoam tech, podiatrist-backed | Cotton dresses & rompers | $65 – $75 |
Olukai | Water activities | Quick-dry lining, arch support | Beachy maxis | $73 – $124 |
KuaiLu | Long walks | Yoga mat footbed, floral strap | Casual sundresses | $15 – $20 |
Yellow Box Feliks | Glam dress-up | Glitter strap, EVA sole | Maxi dresses, night looks | $34 – $45 |
Skechers | Cruise evenings | Rhinestone strap, yoga foam | Neutral midis & palazzos | $33 – $40 |
Flojos Fiesta | Resort glam | Faux leather strap, arch support | Printed dresses | $20 – $35 |
REEF | Eco-conscious style | Recycled materials, arch support | Boho sundresses | $22 – $50 |
Cobian | Day-to-night looks | Thick foam sole, arch support | Wrap dresses & florals | $33 – $40 |
Crocs Platform | Street style & festivals | Croslite platform, customizable | Mini dresses & crop sets | $30 – $40 |
🌞 Style Tips: How to Pair Flip Flops with Dresses
Not all flip flops are created equal—and neither are dresses. The key to nailing a summer-ready look is knowing how to mix and match the right silhouette with the right sandal. Whether you’re dressing up a maxi or keeping it casual in a tank dress, here’s how to style your flip flops for maximum impact (and minimal effort).
- Maxi Dresses: Choose flip flops with a clean, elevated sole like the Olukai Ohana for balance.
- Midi Dresses: Look for supportive arch sandals like DREAM PAIRS or KuaiLu to give your look a put-together edge.
- Mini Dresses: Go playful with printed straps or textured footbeds—try REEF or Rocket Dog.
- Solid Dresses: Add contrast with braided straps, metallic accents, or bold colors.
Final Thoughts
The perfect summer flip flop isn’t just about comfort—it’s about completing your look with intention. Whether you’re chasing sunsets in a flowy maxi or grabbing brunch in your favorite sundress, these cute flip flops prove you don’t need heels to turn heads. From sparkle to support, minimalist to bold, there’s a pair for every mood and dress in your closet. So slip into something easy, chic, and summer-ready—your dresses deserve it.
❓ FAQs About Wearing Flip Flops with Dresses
Q: Can flip flops really look good with dresses?
Absolutely! Choose styles with sleek silhouettes, metallic or braided straps, or soft neutrals that enhance your outfit instead of clashing with it.
Q: What are the most supportive flip flops for walking?
Look for footbeds with arch support or cushioning, like OOFOS, DREAM PAIRS, or KuaiLu. These give you the freedom of a flip flop without sacrificing comfort.
Q: What’s the best flip flop color for matching dresses?
Neutrals like black, tan, or white are versatile, while metallics (gold, silver, rose gold) add polish and can double as a dressier option.
Q: Can I wear flip flops for dinner or out at night?
Yes—choose a pair with a wedge, embellishments, or sparkle (like Yellow Box or Skechers Vinyasa) to level up your look for evening.
More From TheTravelYard
Summer Dresses On Amazon On Sale Now
Affordable Beach Cover Ups for Travel (2025)
18 Summer Tops for Women on Sale Now
Best Matching Shorts Sets for Women (2025)
Knee Length Dresses for Travel: Style, Comfort & Packability
Wide Leg Linen Pants For Women: Flowy Breathable & Perfect For Travel
