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.
Solid & Striped
Felice dress
Hill House Home
The Fleur mini dress
Abercrombie & Fitch
The A&F Scarlett skort
Ekouaer
Henley beach dress
Celandine
Linen-blend Lace T-shirt dress
Halara
Breezeful backless dress
FP Movement
Hot Shot mini dress
Free People
Angel maxi dress
Banana Republic
Linen maxi dress
Abercrombie & Fitch
Beaded flowy midi dress
Abercrombie & Fitch
The A&F Julia maxi dress
Elizabeth Gillett
Ric Rac cover-up
Maeve
Tie-Neck mini kaftan
Free People
Khai one-piece
Free People
Essentially The Best mini dress
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.
Prettygarden
Vest waistcoat and pocket shorts
Solid & Striped
Avril button-down set
Aritzia
Wilfred CruiseLinen Pacino vest & Lodge pant
Petal & Pup
Geneva tie top & midi skirt
Marine Layer
Kiara baby tee & flare pant
Frank & Eileen
Tuscany Getaway set
Saodimallsu
Summer Beach set
Free People
Sailor tube set
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.
Yellow the Label
No crying windbreaker
Alo Yoga Rain or Shine coat
Coalatree Whistler windbreaker
J.Crew
1988 Rollneck sweater
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.
Anrabess crochet cover-up
Monday Swimwear
Montego mini dress
Jenni Kayne
Linen Logo shirt
Show Me Your Mumu
Paula pullover cover-up
Old Navy
Crinkle Gauze pants
Monday Swimwear
St. Barth’s skirt
Monday Swimwear
Jamaica sarong
Farm Rio
Flower Leapards sarong
Farm Rio
Farm Rio x Anthropologie midi slip skirt
Land’s End
Maxi swim cover-up
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.
Todd Snyder
Todd Snyder x Sperry Top-sider Suede boat shoe
Tkees
Lily Nudes flip-flop
Free People
Miko rope slide sandals
Kindred Label Hannah Thong foldable sandal
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.
Lack of Color
The Desert Cowboy straw hat
Secret Charm
Le Playa trucker hat
Madewell
Lantern straw hat
Banana Republic
Straw clutch
Loewe
Loewe x Paula’s Ibiza raffia bucket bag
Mark & Graham
Hat Carrier beach bag
Sea Bags
Cure Pink Lobster tote
Ray-Ban
Frank Legend Gold sunglasses
Brooklinen
Cabana Stripe towel
Huckberry
Mediterranean Turkish towel
R+Co
Cool wind PH Perfect air dry creme
Chums
Neoprene Classics sunglasses strap
Oragift
Multilayer belly chain
Anthropologie
Aimee Claw hair clip set
Free People