Tried and tested: The best resort wear for men in 2025

We all need a break sometimes. Whether you are a summer traveler, finding places to escape your everyday life to and enjoy what most would consider paradise, or you are a person who enjoys the road less traveled and opts for the shoulder season, vacation is a yearly must. For me, I tend to enjoy travel at a very specific time: Every chance I get. Sometimes I want to jet off to Iceland for an adventure following the steps of Vikings. Sometimes I want to face fears in Bonaire. And sometimes, I just need to unplug. Recently, I got a chance to accomplish the latter when I disappeared to South Caicos and holed up at the Sailrock South Caicos. It was the perfect opportunity to hit the reset button and plan the next few years of my life in a literal paradise. Because I have an obsession with men’s style, hence my career choice, it was also an opportunity for me to test out the best resort brands for men. I have narrowed it down to the five brands that served me the best, and span everything from lounging around the pool, hitting the beach, having upscale dinners, or going on excursions.

How I chose these brands

This is one of the hardest parts of my job. I had to find a place to test the brands in the field. That meant jetting off to a resort in paradise so I could put each one to the test. I know, it is a tough job, but someone has to do it. I chose Sail Rock because it offered the perfect combination of luxury in great food, pristine beaches, and great service, adventure with water sports, and serenity with private villas and a spa.

There is only one true way to test whether or not a brand is up to the task, and that is to wear it. I picked up outfits from ten of my favorite brands to give them a shot during a trip to Sailrock South Caicos and narrowed it down to five. Here are the five brands that stood above the rest.

Dandy Del Mar

Not all of the brands on this list are exclusively resort wear, but Dandy Del Mar has set the standard for leisure. They have redefined what the term means and are so dedicated to the concept that their newsletter revolves around it. For me, they own the versatility you need when you go to a resort by offering swim sets and complimentary swim shorts, and the Brisa Suit separates for when you want to elevate your look for dinner.

I wore this set when I picked up drinks at The Cove restaurant at the beach while I waited for Benjamin, a fascinating man who serves as the activities director, to take me out on the sea in a Hobie Cat sailboat. It served me perfectly on and off the beach, making it the best overall choice.

Orlebar Brown

When you think of resort wear, one of the first brands to come to mind for anyone in the industry is Orlebar Brown. If you start to plan your trip and do a simple internet search, they are near the top. There is a good reason for that as they established themselves as one of the most luxurious brands on the market, and their connection to James Bond only deepens that sentiment. With thier recreation of the famous blue swimsuit cover-up Sean Connery wore in Goldfinger, they landed on the scene and stayed near the top ever since.

I elected this white linen button-up and paired it with a pair of swim shorts in a glenn plaid pattern created to honor the famous suit worn by 007 later in the movie. It was the perfect combination for a day on a boat that allowed me to explore the sandbar for starfish, visit Iguana Island for some of the greatest views I’ve ever had of the Atlantic Ocean, and snorkel the reef. It is the most luxurious brand you will find, and it makes it worth the money.

Lululemon

Lululemon is one of the most well-known brand names all over the world for a reason. They offer some of the most comfortable clothing on the market, and that is perfect for when you are looking to take advantage of the reset button when you head to your resort. Whether you are doing yoga, hitting up the spa, or lounging by the pool, you will be in some of the most comfortable clothes in your bag.

For me, I took a day to read a book, lie by the pool, and get a massage in an outbuilding on the peninsula sporting views of both the Atlantic on one side and the Caicos Bank on the other. Before and after the massage, you wouldn’t have been able to find me as I disappeared into my private villa and listened to the ocean while finishing a novel. Light, breathable, and comfortable, not doing anything was easy.

Alex Crane

I didn’t know much about Alex Crane when I packed them in my suitcase before the trip. I hadn’t had any experience with them, so I was curious to see what they had to offer. In my research, I discovered they are dedicated to being environmentally responsible by making their clothing out of natural materials like linen and cotton, and even coconut or banana leaves.

My Alex Crane garment was a matching linen set colored gray with natural dyes and white stripes. Paired with a henley kept it casual enough for lunch and afternoon drinks (it was paradise after all, and Sailrock offers a drink called a Blue Ocean that kept me busy most afternoons), and swapping the henley for a collared button-down made it my most complimented ensemble. If you are an environmentally conscious person looking to look great at your resort, this is the clear choice for you.

VRST

Finally, the fifth and most economical choice on the list goes to VRST. This is a brand sold exclusively in Dick’s Sporting Goods, and this year they released their Resort Wear Collection, which consisted of lightweight and breathable pants and shirts, with a matching beach set. Each piece is under $100 and in the store so it is the perfect selection for the guy who has had it with his daily grind and is making a last-minute getaway.

For my little “work trip” to Sailrock South Caicos, I wore the VRST lightweight pants in a cream color with a tan stripe and a tan tee as I explored the property. An old Coast Guard station, a launching point for fishing boats, and magnificent vistas. Not to mention a breakfast sunrise and multiple old fashionds while watching the sunset. It was the perfect day that would be worth the last-minute purchase and spur-of-the-moment weekend at Sail Rock.

There were a few other workhorses that got some mileage on my trip. I, of course, took my Buck Mason Carry-On Suit for the perfect travel companion and elevated dinner jacket. I sported some Tecovas Mateo slip-ons ons which elevated every one of the outfits with some class and sophisticated resort style. And a white short-sleeve henley from HNLY that looked amazing and felt even better. And, finally, there was a need for a durable and versatile watch to take with me on excursions or finish my looks and Luminox took their legendary Navy Seal 3500 Series and created a stealth-inspired blackout timepiece that was my constant companion through the entire trip.

Everyone needs a getaway. There are none better than the kind you can make your own by either feeding the adventurous part of your soul or taking a much deserved recharging vacation. Sailrock South Caicos is the perfect place to do either, and these five brands will help you make it stylish and comfortable.