Sunset Cruise Outfits: What to Wear on the Water

For a sunset cruise, wear a relaxed, casual outfit, flat shoes with rubber soles, and bring a warm, wind-blocking layer: a hoodie, crewneck or light shell. In summer that layer can live in your bag. In spring and fall, when Rhode Island evenings on the water turn cool fast, plan to wear it for most of the ride and add a hat and warm socks.

The ride back after the sun goes down is the part most people dress for wrong. If you need that outer layer, start with our Block Island sweatshirts and hoodies, and keep a cap that will stay put in the wind from our Block Island hats.

Quick answer

• Casual or smart-casual is right for nearly every public sunset sail or harbor cruise. Skip swimwear and gym clothes.
• Bring one more layer than the dock temperature suggests. In shoulder season, bring two.
• Choose flat, closed-toe shoes with non-slip rubber soles. Heels, smooth soles and flip-flops are the real hazards on a wet deck.
• Keep your hands free: a small zip bag, sunglasses with a strap, a hat that will not blow away.
• Follow the crew's life jacket instructions. Pick layers that fit comfortably under one.

Why the water feels colder than the dock

A sunset cruise puts you in three conditions in one trip. You board in still, sheltered dock air. Out on open water, wind and spray make it feel cooler. Then the sun drops and the air temperature follows it. The dock is usually the warmest place you will be all evening.

That gap grows in late spring and fall. A mild afternoon on land can become a cold evening on the water once the breeze comes off Block Island Sound or Narragansett Bay. Check the forecast for the hour you will be coming back, not the afternoon high, and dress for that.

Start with the base outfit

Your base layer is what shows in the photos. Keep it comfortable and easy to move in.

• Summer: a sundress or romper with a hem that will not whip around, linen pants or chino shorts with a polo, or a tee under an overshirt.
• Spring and fall: jeans or chinos, a long-sleeve tee or button-down, and leave the shorts at home. Long sleeves under a sweatshirt are warmer than a sweatshirt alone.
• Fabrics: cotton and light knits layer well. Heavy denim stays damp if spray hits it, so keep a dry layer on top.
• Colors: soft neutrals, blues and sage photograph well against a sunset sky. Bright white shows every splash.

Shoes: the choice that decides your evening

This is the one place to put function ahead of looks. Smooth leather or plastic soles give you almost no grip on a wet deck.

1. Best: boat shoes, clean rubber-soled sneakers, or flat sandals with a heel strap and a gripping sole in warm weather.
2. Acceptable: soft-soled flats on a large, steady boat with a dry deck.
3. Leave at home: stilettos, platforms, wedges, smooth-soled loafers and flip-flops.

In cool weather, closed shoes matter twice: for grip and for warmth. Cold toes on deck are what make people head inside early, so pair your sneakers with a real pair of crew socks. Our nautical socks are $12.99 a pair, or any 2 pairs for $20.

The layer you will be glad you packed

Treat the outer layer as part of the outfit, not an emergency item. In order of wind protection:

• A light windbreaker or shell. Wind is what makes a boat feel cold, and a thin shell blocks it better than a thick knit.
• A zip hoodie. The hood works as a wind guard, and the zip lets you adjust as the temperature drops without pulling anything over your hair.
• A crewneck sweatshirt. Warm and simple for calm harbors. On a breezy night, wear it under a shell.

Not sure whether you need a sweatshirt, a jacket or both? Our guide to choosing between a sweatshirt and a jacket walks through it.

What to wear by season

For a private dinner charter, dress one step up (a collared shirt or a midi dress) and ask the operator about any dress code when you book.

Safety first: layers and life jackets

The U.S. Coast Guard's guidance is simple: a life jacket can only help if you are wearing it. On any commercial cruise, the crew will tell you where jackets are and when to put them on. Follow those instructions, and make sure children wear a properly fitted jacket before the boat leaves the dock. Put your warm layer on first and the life jacket over it. Keep young children off your shoulders near the rail, where a sudden roll can throw you off balance.

Block Island layers for the ride back

If you want a layer that fits a sunset on Rhode Island water, these are the pieces we would point you to:

• The Technically New Shoreham Full-Zip Hoodie ($54.99) has a full zip, lined hood and split pouch pocket, in Black, Navy or Dark Heather, sizes S–3XL.
• The Last Boat Club Hoodie ($44.99) carries a ferry-and-sunset print on the back.
• The Ferry Standard Time Crewneck (from $44.99) is printed on a garment-dyed Comfort Colors crewneck with a relaxed unisex fit.
• The Block Island Retro Sunset Rope Cap ($34.99) has an embroidered retro sunset over waves, a braided rope trim and an adjustable snapback.

Building a full coastal look beyond the boat? See our guide to New England coastal style.

A packing list for the evening

1. A hoodie, crewneck or windbreaker (both, from September on).
2. Flat, non-slip shoes and warm crew socks.
3. Sunglasses with a strap.
4. A cap with an adjustable back, or a knit hat for the ride back.
5. A phone in a zip pouch, and hair ties for long hair.
6. A small bag with a zipper or a flap. An open tote is easy to lose to a gust.

Common mistakes

• Dressing for the dock. It is the warmest spot of the evening.
• Trusting the afternoon high in fall. Check the temperature for your return time.
• Wearing heels for the photo. Everything else in this guide is flexible. This is not.
• Bringing a wrap you cannot secure. If it can blow away, it will.

FAQ

What should I wear on a sunset cruise?

A casual outfit such as a sundress, polo with chinos, or jeans with a long-sleeve tee in cooler months. Wear flat, non-slip shoes and bring a hoodie, sweatshirt or windbreaker for the ride back.

Is it cold on a boat at sunset?

Usually colder than the dock. Wind on open water and the setting sun both lower the temperature, and the ride back is often the coldest part. In spring and fall, plan to wear your warm layer most of the trip.

What should I wear on a fall sunset cruise in Rhode Island?

Jeans or chinos, a long-sleeve base, a sweatshirt or zip hoodie, and a wind shell if it is breezy. Add closed rubber-soled shoes, warm socks and a hat.

What shoes are safe on a boat deck?

Flat shoes with rubber, non-slip soles. Avoid heels, smooth leather soles and flip-flops, which grip poorly on a wet deck.

Ready for the ride back?

Pick your layer from our Block Island sweatshirts and hoodies, add a Block Island hat and a pair of nautical socks. Every piece is made to order by our print partners. Shipping is $5.95 on orders under $50 and free on US orders of $50 or more after discounts, and Bundle & Save takes 20% off 3 or more items from our Bundle & Save collection. Returns are accepted within 30 days.