Whether you’re hopping on a chartered sailboat in Montauk, cruising with friends off the coast of Nantucket, or setting out on a sunrise yacht in Miami, your boat trip outfit should strike a balance between function and effortless style. You’re after a breezy, nautical look—comfortable lightweight linen sets, classic stripes, flowy sundresses that catch the wind just right, and chic cover-ups that double as beach picnic-ready looks are just the ticket to putting it together. Footwear matters, too: Opt for nonslip sandals or boat shoes that are equal parts stylish and practical. The trick is staying warm when the breeze picks up—so pack a soft sweater or oversized button-down to layer over your swimwear. And don’t forget a strong SPF, a wide-brimmed summer hat, and a pair sunglasses to top it all off.
When done right, coastal chic never goes out of style—and with accessories, it’s the kind of look that carries from dock to dinner seamlessly. Whether you lean more timeless or trendy, we’ve rounded up everything you need to wear (and bring) on board to make your next boat day that much more aesthetic—and a whole lot more comfortable.
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Dresses, jumpsuits, and more
Easy, breathable, and perfectly-in-sync with sun, breeze, and ocean views, dresses and jumpsuits make a great base for boat outfits. We’ve compiled a list where fashion meets function—with airy styles that flow with the sea breeze and transition effortlessly from day to sunset drinks. Whether tossed over a bathing suit or styled solo, these picks avoid the cling and friction of denim or tight clothes against damp skin. Chic staples, like Free People’s Eden jumpsuit or Anthropologie’s Elizabeth Gillet dress, actually do feel as good as they look.
Stylish summer sets
Matching sets are everywhere this summer, and they’re perfect for boat days when you want to look put-together with minimal effort. We’ve got you covered with crisp linen button-downs with elastic-waist shorts, gauzy cropped tops with flowy trousers, and terry sets that double as towels post-swim. Whether you go for a fun, bold stripe (see, the yellow block-stripe pick from Marine Layer) or a washed-out, goes-with-anything neutral, these sets are functional enough to wear over a bathing suit and polished enough to take you straight to a dockside dinner. Lightweight and breathable, they move with the breeze and dry fast—ideal when the sea spray hits.
Outerwear and windbreakers
From laid-back boat days to parking somewhere for a swim or setting up a sun-soaked beach picnic, waterproof and cozy outerwear is the way to go, especially when you’re definitely jumping into the water. Think of them as low-effort, high-comfort essentials: A breezy windbreaker or a soft cotton tunic easily slips over any dampness without sticking to wet skin. Lightweight sweaters or light ponchos come in handy when the breeze kicks up or the sun dips earlier than expected. A water-resistant layer is smart to have on hand—especially if you’re out all day or heading back at dusk. These pieces aren’t about being precious—they’re about staying warm, dry, and comfortable while still looking pulled-together.
Cover-ups and sarongs
Cover-ups and sarongs are the ultimate in-between pieces—perfect for that moment when you’re fresh out of the water, still drying off, and it’s too warm (or too soon) to fully change back into your outfit. They pack light, dry fast, and add just enough style without sacrificing comfort. A classic sarong like the Shu-Shi beach sarong ties easily at the waist or over the shoulder for full versatility, while Farm Rio’s Flower Leopards sarong brings a bold print that feels elevated but playful. The Lspace Anna cover-up is effortlessly breezy with a hint of shape, ideal for slipping on and looking chic between swims.
Sandals, flip-flops, and boat shoes
When it comes to boat footwear, nonslip sandals and flip-flops are essential—not just for comfort, but for safety. It’s tempting to go all-in on fashion, but the reality is that wet decks and wobbly footing don’t mix well with unstable shoes (yes, even a platform heel for an onboard dinner can trip you up—I’ve learned this the hard way). The good news: There are plenty of tasteful options that also hold up on slippery surfaces. Look for sandals with rubber soles, adjustable straps, or textured footbeds that offer grip without sacrificing style. Sleek leather slides, minimalist sporty pairs, or modern fisherman sandals check all the boxes. They’re easy to rinse off, comfortable to wear all day, and transition seamlessly from boat to dock to dinner—no outfit compromise required.
Boat day accessories
Accessories can make or break your boat day—a few practical touches go a long way in keeping you comfortable, pulled-together, and ready for wherever the boat takes you. Start with a smaller, water-resistant bag or pouch that keeps essentials close without weighing you down. Beach totes and bucket bags are best to keep your belongings from getting soaked. Wide-brimmed hats and trendy straw hats are a must for shade and style. Other accessories you might not have on your radar: windproof hair cream, to keep flyaways under control, and a strap for your sunglasses. (They’ve made a comeback, and no one wants to watch their favorite pair sink.) Pack a quick-dry towel—Turkish towels are known to be the lightest—and sunglasses that are fitting, flattering, and polarized.
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