Skip to main content

Sailing in Style: What to Wear on a Boat

The date’s set, your bags are (almost) packed, heck, the boat’s at the dock. Don’t head out of town yet, though: You’re going to need to know what to wear on a boat, and as soon as possible, at that. Take a little old-school inspiration in the form of a rugged fisherman’s sweater, throw on some tailored swim shorts, step out in boat shoes that are land and water-ready, then consider yourself geared up to hit the water in style.

After all, this is no time to pull any punches. You might meet relentless or driving winds on the water, and perhaps on the same day — there’s no excuse not to be ready to embrace whatever the high seas (or the lake, or the river!) bring your way. Our stylish picks for what to wear on a boat can help cast off the right way.

Recommended Videos

Pedro and Tailor Tee  

Pedro and Tailor Tee
Image used with permission by copyright holder

A T-shirt becomes more than just a T-shirt if you find the right one, and Pedro & Tailor has carefully crafted this essential tee to work more than stylish no matter where it goes (yes, on and off the boat). Made with soft, American-grown Supima cotton, it’s a tasteful and cool summer tee you can wear to grab a beer back on the mainland.

Buy at Pedro and Tailor

Howler Brothers Aguacero Jacket

Howler Brothers Aguacero Jacket
Image used with permission by copyright holder

Hey, we told you it could get choppy and windy out there. Keep this functional, adventure-ready rain jacket on hand from a brand that knows a few things about the great outdoors.

Buy at Howler Brothers

Huckberry Canvas Snapback

Image used with permission by copyright holder

Every guy needs a well-worn, much-loved hat with some stories to go along with it. For tales of adventure (and relaxing days) on the water, get this durable, cool-as-heck canvas snapback from Huckberry.

Buy at Huckberry

Beau Hayhoe
Beau Hayhoe is a freelance men's style writer, consultant and PR pro based in Brooklyn. Beau's menswear and gear writing has…
Style corner: How to wear men’s shorts in style in 2025
Showing off your legs the right way in 2025
Faherty All Day Short stacks

The summer is here. The spring showers have given way to the hot days, and that means it is time to start wearing clothing that protects you from the sweltering temperatures with a new summer wardrobe. And it also means that great summer vacations are on the horizon, and you need something to pack that will look great and keep you comfortable. For us, that means men's shorts are top of the pile for the next 12-15 weeks. Whether we're looking for something to wear around the house, out and about on errands, or something to keep us comfortable while exploring new places outside the office, a great pair of men's shorts is essential for our summer.

But these are not just any old pair of cut-off pants that we can wear. No, we have to put some thought into the shorts. Since I'm a huge fan of talking to people smarter than me to figure out the best way to do things, I reached out to Mike Faherty, co-founder of Faherty, to get some insight on how to wear shorts in 2025.

Read more
The power suit is back: An expert guide to wearing it in 2025
The men's style classic brings back the authority of the 80s man
Man in power suit

Whether you are a fan of the fictional Gordon Gecko in Wall Street or more of a real-life kind of guy, rewatching Leonardo DiCaprio's Jordan Belfort in The Wolf of Wall Street, one thing that you can't deny is that the men knew how to dress. But it wasn't about fashion. It was never about fashion. These men, and countless other nameless men who wore men's suits in the 1980s, stumbled onto something more. The power suit was, of course, a part of the man's wardrobe throughout the decade, but what started as a style staple quickly evolved into a statement. The power suit projected wealth, status, and authority. When you saw these men on the street, you wanted to follow them, learn from them, and become a Wolf of Wall Street in your own right.

Now, we're seeing a return of the power suit. We are watching as men reclaim their authority, strive for their wealth, and become leaders before they even step out the door. But what is the cause? Why did they show back up? Or an even better question, did they ever truly leave? At the end of the day, this is about men reemerging from a pandemic and a general sense of uncertainty to take charge of their destinies, just as their fathers, grandfathers, and all the men of the past did. But like any men's style arena, there are some guidelines you can follow to help you capture the past without looking outdated. We reached out to Alberto Gil, co-founder of Hockerty, to have him walk us through how to wear the 80s power suit four decades after its heyday.

Read more
Aimé Leon Dore and New Balance remix their sleek slip-on style
Aimé Leon Dore, New Balance release new slip-on shoe
man holding Aimé Leon Dore x new balance neon yellow shoe

When it comes to seasonal releases, no pair works harder than Aimé Leon Dore and New Balance. These partners have constantly offered fans new looks each season; summer 2025 is no exception. Fresh off their first season collection, the duo is once again providing us with a must-have shoe for the summer. With a trio of new designs, Aimé Leon Dore and New Balance are taking to one of the brand’s lesser-known silhouettes for an edgier look. Although chunky sneakers were once the hottest shoe, it’s no secret that slimmed-down footwear has once again gained traction. Models like the Adidas Samba and Puma Speedcat have caught everyone’s eye for their subdued silhouette, and this new offering from Aimé Leon Dore and New Balance follows suit. 

Aimé Leon Dore and New Balance’s MT10T slips into a new look

Read more