The best summer outfits aren't complicated. They're one great dress and one great pair of sandals, and you're out the door.
That's the idea behind this lookbook: four complete, head-to-toe outfits using our Charlee cotton dresses paired with sandals that match the vibe, the occasion, and the comfort level you need. No overthinking. No outfit anxiety. Just grab a dress, step into the right sandal, and your look is done.
Every dress on this list is made from breathable cotton, designed for real bodies, and pairs effortlessly with the sandals we've matched them with. And every sandal is machine washable, bunion-friendly, and comfortable enough to wear from morning to night. Because summer is too short to spend it in uncomfortable clothes.
Look 1: Tropical Getaway
Reece Dress + Hunter Slide Sandal
The dress: The Reece Dress ($188) is the kind of print that makes people ask where you're going on vacation, even if you're just headed to brunch. Available in Bird Paradise Blue and Bird Paradise Orange, it's bold, joyful, and unapologetically tropical. The cotton fabric keeps things breathable, and the relaxed silhouette moves with you whether you're walking the boardwalk or sitting at a patio table.
The sandal: The Hunter Slide Sandal ($147) was made for this dress. The soft linen elastic upper features bold coastal stripes and a statement tortoise buckle that picks up the resort energy of the Reece without competing with the print. The lightweight blown rubber espadrille sole is shock-absorbing and incredibly light, so it feels like walking on a cloud.
Why they work together: Bold print dress + striped slide sandal sounds like it could clash, but the secret is the color palette. The Hunter's linen stripes (available in Navy, Pink, and Orange) are tonal enough to complement the Reece's tropical print without fighting for attention. It's the kind of pattern mixing that looks intentional and effortless at the same time. As Who What Wear's 2026 summer sandal styling guide notes, the strongest summer outfits this season pair textured sandals with printed dresses and keep everything else minimal.
Where to wear it: Resort dinners, vacation days, tropical brunch, summer parties, anywhere you want your outfit to do the talking.
Styling tip: Keep jewelry minimal. Gold hoops or a simple pendant let the dress and sandal do the work. Oversized sunglasses and a woven tote bag complete the look.
Look 2: Polished Coastal Classic
Sophia Dress + Carolina Sandal
The dress: The Sophia Dress (from $169) is what happens when a shirtdress and a beach cover-up have a very stylish baby. It's a 100% cotton shift-style shirtdress with a collar, three-button placket, tab sleeves, and deep side pockets. The above-knee length keeps it breezy, and prints like Navy Fish, Navy Palm, and Blue Stripe bring coastal charm without overdoing it. Machine washable, because of course it is.
The sandal: The Carolina Sandal (from $150) adds a polished, feminine touch with its faux espadrille wedge heel and wrap-around ankle straps. The playful frayed strap detail gives it personality, and the plush cushion insole keeps every step comfortable from morning to night. This is the sandal that takes a casual dress and makes it look like an outfit.
Why they work together: The Sophia is structured enough to feel put-together but relaxed enough for summer. The Carolina's wedge heel adds just the right amount of lift to make the shirtdress silhouette feel intentional rather than thrown-on. Together they hit that "elevated casual" sweet spot that Oui Magazine calls the defining summer 2026 style: light, feminine, and easy to adapt to different moments.
Where to wear it: Work (especially casual offices or creative environments), client lunches, weekend sightseeing, day-to-night transition outfits, travel days when you want to look polished without effort.
Styling tip: The pockets are the Sophia's superpower. Skip the big bag and go with a small crossbody or clutch. A straw belt at the waist adds shape if you want more definition.
Look 3: Easy Everyday
Madi Dress + Peachtree Sandal
The dress: The Madi Dress ($198) in Blue/White Stripe is the summer dress that makes every woman look effortlessly French. Clean lines, classic stripes, and a relaxed fit that flatters without clinging. It's the dress you grab for the farmers market, the school pickup line, and the last-minute dinner invitation all in the same day.
The sandal: The Peachtree Sandal ($138) is our most versatile flat sandal and one of our best sellers. The 1-inch faux espadrille wedge gives you just enough lift to elongate your legs without changing how you walk. Crisscross straps with a heel cup keep your foot secure, the elastic construction is bunion-friendly, and the padded insole cushions every step. Available in 10+ colors.
Why they work together: This is the pairing for women who want to look good without thinking about it. Blue and white stripes are universally flattering, and the Peachtree in Linen, Navy, or Black grounds the look with an easy, goes-with-everything sandal. As Fashion Story Dress's 2026 summer outfit guide recommends, the strongest everyday summer looks keep the dress as the statement and let the shoes stay simple and comfortable.
Where to wear it: Literally everywhere. Errands, brunch, farmers markets, school events, casual dinners, travel days, weekends at the beach house. This is the look you'll wear more than any other this summer.
Styling tip: The Peachtree comes in so many colors that you can change the feel of this outfit just by swapping the sandal. Linen for a neutral look, Pimiento for a pop of color, Navy for a tonal blue-on-blue vibe.
Look 4: Dinner-Ready Showstopper
Kelly Dress + Angela Sandal
The dress: The Kelly Dress ($178) is the one you reach for when the occasion calls for something special. Available in Positano Blue and Hibiscus Floral, it's bold, beautiful, and designed to turn heads. The cotton fabric keeps it breathable for warm summer evenings, and the silhouette is the kind that photographs beautifully.
The sandal: The Angela Platform Wedge Sandal ($152) gives you the height and drama of a heel without any of the instability. The platform under the forefoot offsets the wedge, so it feels much lower than it measures. Two unique toe straps (one fully elastic for bunion-friendly flexibility, one lined for structure) keep your foot secure through hours of standing, dancing, and walking. Machine washable.
Why they work together: The Kelly is a statement dress, so it needs a sandal that can hold its own without competing. The Angela's platform wedge provides the height to give the dress the silhouette it deserves, while the clean, minimal strap design lets the print do the talking. This is the dress-and-sandal combination for summer weddings, rooftop dinners, rehearsal events, and any night when you want to feel like the best-dressed person in the room.
As Who What Wear's summer 2026 dress trend report notes, this season's boldest dresses are styled with statement-making sandals rather than basic heels, and a platform wedge is the ideal partner for a floral print.
Where to wear it: Summer weddings, rehearsal dinners, date nights, rooftop events, vacation dinners, any occasion where you want to feel special.
Styling tip: Let the Kelly and Angela do the heavy lifting. Simple gold jewelry, a clutch in a color pulled from the dress print, and you're done. The wedge gives you height for dancing without the regret of wearing heels.
How to Pick the Right Sandal for Your Summer Dress
Not sure which sandal style works with which dress? Here's a quick framework:
Printed or bold dress → Keep the sandal simple. A neutral slide like the Hunter or a low wedge like the Peachtree lets the dress be the star. Don't compete with the print.
Solid or stripe dress → Go bolder with the sandal. This is where a wrap-strap sandal like the Carolina or a platform wedge like the Angela adds personality to a simpler dress.
Casual daytime plans → Flat or low wedge. The Peachtree (1-inch wedge) or the Hunter (flat slide) keep things relaxed and comfortable for all-day wear.
Dinner or events → Wedge or platform. The Carolina (espadrille wedge) or the Angela (platform wedge) give you the height and polish that evening occasions call for.
Day-to-night versatility → Mid-height wedge. The Carolina hits the sweet spot. Comfortable enough for a full day of plans, elevated enough for dinner afterward.
Why Cotton Dresses and Machine Washable Sandals Are the Ultimate Summer Combination
Summer is messy. Sunscreen, sand, sweat, popsicle drips, restaurant patios, grass stains. Your clothes take a beating, and replacing them every few weeks isn't the answer.
Every Charlee dress on this list is made from 100% cotton, which means it's breathable, soft against your skin, and gets better with every wash. Every sandal is machine washable (or easy to clean), so a weekend of summer chaos doesn't end your favorite pair's life.
That's the Charleston Shoe Co. difference. Our dresses are designed by Neely Powell and Alexis McHarg using artisan block printing techniques in India, and our sandals are handmade by artisan cobblers in Mexico and Spain. Head-to-toe pieces that are made to be lived in, not just looked at.
Shop all Charlee dresses and browse the full sandal collection to build your own summer looks.
Frequently Asked Questions
What sandals look best with summer dresses?
The best sandals for summer dresses depend on the dress style and the occasion. For casual cotton dresses, flat slides and low wedges (1 inch) keep things relaxed and easy. For polished shirtdresses, an espadrille wedge with ankle straps adds structure and femininity. For bold printed dresses and evening occasions, platform wedges provide height and drama without instability. The key is matching the sandal's formality to the dress.
Can you wear flat sandals with dresses?
Yes. Flat sandals and low wedge sandals are one of the easiest, most comfortable ways to style a summer dress. They create a relaxed, effortless look that works for everyday outfits, casual events, and travel. For a slightly more polished appearance, choose a flat sandal with a small wedge (half an inch to one inch) rather than a completely flat sole, as it adds a subtle lift that elongates the legs.
What are the best comfortable dress sandals?
The most comfortable dress sandals have cushioned insoles, elastic or stretch straps that flex with your foot, and a low wedge or platform that distributes weight evenly. Espadrille wedges with padded footbeds are especially good because they combine the look of a heeled sandal with the comfort of a flat. Machine washable construction is a practical bonus for sandals you'll wear frequently.
How do you go from day to night in the same outfit?
The easiest day-to-night transition is a versatile dress paired with a mid-height wedge sandal (1.5 to 2.5 inches). The wedge is comfortable enough for daytime errands and walking but polished enough for dinner and evening plans. Swap accessories to elevate the look: add gold jewelry, switch to a clutch, or layer on a lightweight jacket. The outfit stays the same, but the energy shifts.
Are wedge sandals good for summer weddings?
Wedge sandals are one of the best options for summer weddings, especially outdoor events. The wider sole won't sink into grass or sand, and the continuous heel provides stability for standing and dancing. Platform wedges are particularly good for weddings because the platform offsets the heel height, giving you dramatic elevation that still feels comfortable after several hours.
What is resort wear?
Resort wear refers to clothing and accessories designed for warm-weather travel, vacations, and leisure. It typically includes breezy dresses, linen separates, sandals, and accessories in tropical prints, bold colors, or relaxed neutrals. The key quality of resort wear is versatility: pieces that transition from the beach or pool to dinner without a full outfit change. Cotton dresses paired with espadrille wedges or slide sandals are a classic resort wear combination.