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4 min readNOT SURE ABOUT you, but I’m due for a vacation like, yesterday. This past winter on the East Coast didn’t do me any favors. And while I’d love a nice Eurotrip, it’s been a long year, and I’m thinking a less labor-intensive form of travel. In other words, I want to spend 12 full hours in a swim-up bar or passed out on a beach. There’s only one real way to do that: an all-inclusive resort. Or any resort, really.
Doing basically nothing for seven days and seven nights (other than working on my tan) is a dream come true. One of the underrated aspects of vacationing at a swanky resort is playing dress-up. If I could wear vacation fits every day, I would. But the occasionality makes it that much sweeter. Otherwise, I’d look like a permanent cast member of The White Lotus, and I don’t want to die.
Pulling off resortwear tastefully isn’t as easy as it sounds. There’s a fine line between “fun” and “tacky.” As Men’s Health resident beach bum, I went through some of the best ways to pull off the vacation look without going full “unc.” Spoiler alert: there are no fanny packs involved.
A Breezy, Fun Shirt
Resortwear has come a long way from the classic “dad” look. Our editors love Todd Snyder’s Capri Shirt. It’s made from a silky-smooth, lightweight fabric that can get you through even the hottest days. For something a little more dinner-appropriate, Brooks Brothers’ Friday Shirt is one of my go-tos, and its Poplin Stripes scream summer. J-Crew makes a similar Poplin shirt for under $100 and available in plenty of styles.
For a slightly more elevated look, we’d suggest Todd Snyder’s Montauk Sweater Polo. It’s made of a refined cotton-linen blend that’s comfortable, stylish, and most importantly, breathable. If you’re looking for a “party” shirt that’s a little more subtle, Tommy Bahama’s silk panel back camp shirt is the perfect middle ground. You’ll appreciate the relaxed fit, too.
Linen Pants or Lightweight Shorts
There really are two primary options for the resort. Well, three if you count swim trunks (more of that later). A pair of drawstring linen-blend beach pants goes a long way, and Uniqlo makes a pair that’s pretty budget-friendly, especially if you catch it on sale. For a more formal look, go with the Italian Linen Sutton Trouser from Todd Snyder. They’re super soft and can be worn with a basic tee, blazer, or the full suit combo. Rock it with the Italian Striped Linen Sutton Jacket for a beach-approved full fit. The Collins Slim Linen-Blend Trousers from Abercrombie & Fitch are a budget-friendly alternative made from a linen-cotton blend that’ll save you a few bucks.
As for shorts, we recommend a simple pair of cotton shorts, such as the Weekender pull-on shorts from Banana Republic. They’re inherently versatile and feature both a functional fly and an elastic waistband for all-day comfort. I’m also a huge fan of Psycho Bunny’s Knit Honeycomb shorts. They’re made to breathe and feel like a pair of sweats.
Beachy Footwear
Footwear might be the easiest part, but there are subtle ways to improve the look. I’m not a huge fan of a thong flip-flop, and athletic slides are out of the question, but Faherty makes a great suede slide that’s the best of both worlds. It’s dressy enough to wear to formal occasions, but comfy enough for everything in between.
On the other hand, I’m a huge fan of boat shoes, and they go with pretty much any of the styles here. SeaVees dropped a limited-edition capsule pair, and they hold up to my favorite pair of Sperrys. And needless to say, you also can’t go wrong with the latter. For dressier nights, loafers are always a safe bet, and you can never go wrong with Florsheim. You’re also going to want a pair of shoes for the airport and/or days you mosey off the island. You can’t go wrong with a classic white tennis sneaker, and Cole Haan has you covered.
Killer Swim Trunks
I’ll be spending most of my time in the water, so I have to look good doing it. Swimwear is a key component of the look, and if you’re anything like me, you’ll bring a few options. Fair Harbor’s Bayberry Trunk is a favorite among our editors, and it comes in a bunch of different styles and colorways. The brand’s Anchor Trunk is a solid alternative (or addition). If you’re looking for something a little fancier for pool parties, beach clubs, or just looking good, Orlebar Brown offers the best luxury swimwear out there. The Bulldog is our go-to.
For something a little more performance-forward, Huckberry’s in-house brand, Proof, makes a great pair of lined swim trunks. They come in sleek, solid colorways as well as some funky patterns. You’ll definitely want these if you booked a few excursions.
Shades to Round out the Fit
Sunglasses tie together the whole look. Don’t sleep on them—you’ll technically be wearing them the most. A classic pair of tortoise shades works great in the summer. The Harris Glasses from Warby Parker are a fantastic budget alternative to Ray-Ban Wayfarers, but you can’t go wrong either way. If you’re more of an aviator guy, we’d suggest anything from Randolph. If you’re itching to splurge before vacation, these rectangular sunglasses from Oliver Peoples are worth shelling out extra for.
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Tim Kohut is the Deals and Trends Editor for Popular Mechanics, Men’s Health, Best Products, and Runner's World. He has extensive product review and gear coverage expertise, particularly in tech, home, auto, and health. Tim was previously the Deputy Commerce Editor of The Drive and a Commerce Editor at BGR. He’s also overseen gear coverage and strategy at Popular Science, Bob Vila, Outdoor Life, and Field and Stream. He has a strong affinity for cats, Batman, and early 90’s Nicolas Cage films, in that order.
Eunice Lucero-Lee is the Deputy Editor, Deals and Trends, for Best Products, Popular Mechanics, Runner’s World, Bicycling, and Biography. Her obsession with beauty and pop culture keeps her on top of the latest trends and viral online finds, which can also be seen in her work spearheading the Hearst Enthusiast Group’s sales and deals content. Her editorials have been featured in publications like Cosmopolitan, Esquire, The Numinous, woman&home, and Sparkling, among many others. A former music editor, she pioneered Asia’s first-ever English-helmed K-Pop magazine and has extensive experience with celebrity profiling and red-carpet reportage. She is based in Manhattan where she watches Scandi-noir crime procedurals with her cat.
