The thrill and the stress of a packed summer calendar means you’ll need more than a pair of worn-in jeans to get by. Whether you’re jetting off to Europe for your annual holiday, staying put for a long weekend in the city, or pursuing the nearest body of water on a summer Friday, now is the time to perk up your slumbering wardrobe.
From a train-friendly ensemble to chic wedding guest-ready look and a city outfit perfect for quiet cultural exploration, we’ve curated eight looks for every kind of summer weekend escape, featuring plenty of the season’s It items—capri pants, shield sunglasses, and flip flops. Wherever you’re headed, this is how to do it in style.
Staycation
Long weekends are a great time to rediscover your own city. Explore the typically crowded exhibits and shows, and finally snag that impossible dinner reservation. Black capri pants feel distinctly now, pair yours with a classic white tee, a mini tote, and a colored shirt cinched at the waist.
Beach-Bound
For a minimalist take on beachwear, try a black one-piece swimsuit, breezy linen separates, classic flip flops, and Staud’s wood-beaded bag for a timeless ensemble.
A Nautical Afternoon
When the summer heat calls you to the water, lean into the maritime mood with a striped bathing suit, board shorts, and boat shoes. The ocean spray might add a little chill, so keep a nylon jacket handy for when you’re out in the open.
Americana With a Twist
For a classic Americana look with a fashionable twist, pair a white matching set with red and blue accessories. Think holiday-ready, but not on the rose.
Date Night
Date night in the city is open to endless possibilities. For nights where you don’t know where you will end up, a lace cami, rinse wash jeans, a little pouch bag, and strappy heels is your go-to formula.
Rooftop Barbecue
A boho top and jeans is the ultimate BBQ cheat code. It’s comfy enough for seconds (and thirds), while still looking cute and considered.
Lakeside Escape
For a laid-back weekend by the water, keep things casual but thoughtful. Playing with color is key here: Everybody World’s turquoise shorts are laid-back with a twist and pair perfectly over a bright red bikini for spontaneous swims. A baseball cap serves as sun protection—and defense against bad hair days—while Miu Miu’s flip flops are built for dock-hopping.
Wedding Guest Weekend
For those attending a wedding over the weekend, we suggest investing in items you’ll want to wear again this summer—like Anine Bing’s ’90s slip dress, Jimmy Choo’s classic pumps, and Sophie Buhai’s beaded earrings.
