Resort Wear for Men: How to Vacation in Style

The cold weather is setting in and the days are getting shorter—literally. If you’re anything like us, a sunny vacation is a much needed escape. Looking for a sign? This is it. Go ahead, click “purchase” on those airline tickets and get ready to pack your suitcase. Wondering what to pack for a warm-weather holiday while you’re currently living in what feels like sub-zero winter temps? A quick online search will lead you to one answer: men’s resort wear

What Is Resort Wear?

Not sure what the niche clothing category of resort wear means, especially when it comes to men’s fashion? It’s okay, we’re here to help. Resort wear, also commonly called cruise wear, refers to clothing worn on vacation, often in warm-weather destinations. Fun fact: It actually began as a trend among the jet-setting elites and socialists. Over the years, this fad has trickled down to anyone looking to vacation in style, no matter the season. This menswear trend is also on our list of top winter 2022 fashion trends. Think shorts, T-shirts and short-sleeve button-down shirts in lightweight fabrics and colorful hues. Cotton and linen are key fabrics for humid locations, as they are cool and comfortable to wear. Bonus points for the durable and breathable elements they provide. Vacation super-fabrics, if you ask us.

Below, we break down all the specifics of resort wear for men to make your shopping list a little easier. Rest assured, we’re talking items that pack well and wash easily. Sit back, relax and read on to find out what pieces are non-negotiables for your suitcase. Our number one packing tip? Don’t forget the SPF.

Cruise Resort Wear

Booked a trip at sea? Lucky you. Long days spent sailing the open waters will surely have you ready to hit the lido deck. Need a little warm-weather wardrobe refresh to get you ready? For poolside resort wear, you can’t go wrong with men’s swim trunks, tank tops and, yes, those non-slip rubber slide sandals. Lean into the nautical theme by trying out navy and white striped trunks or be bold with an on-trend pattern. We love conversation prints like lobsters or anchors.

To make the most of your trip, book a variety of shore excursions at each port. Get ready to get going. Resort wear works for an active lifestyle, too. Got ziplining on your itinerary? Opt for a pair of longer board shorts or lightweight performance joggers for your trip down the wire. Exploring the local town? Keep it casual in lightweight shorts, T-shirts and flip-flops. Always consider the activities you plan to do on and off of the ship so you are ready for every adventure.

There’s never a shortage of nightlife on a cruise. From formal dinners to comedy shows and casino nights, the options are endless. But what type of resort wear is best for these occasions? It depends and can vary greatly. Before you head out of your cabin, make sure to double check the event dress code. Jackets and ties could top the list for a captain’s dinner. For more informal affairs, a seersucker shirt will fit the bill and give off major yacht rock vibes. Tuck your shirt into a pair of slim-fit light colored pants and slip on a pair of boat shoes. You didn’t think we’d let you get off the ship without rocking boat shoes, did you?

Beach Resort Wear

Are sandy beaches, crystal clear waters and all-inclusive experiences more your speed? You’re in luck because men’s beach resort wear is just the thing for, well, resorts. Shocking, we know. No matter your destination, show up in style by incorporating color, texture and print into your wardrobe. Keep reading for a breakdown of our favorite essentials to take along when heading beachside.

What to Wear to a Cancun Resort

A Mexican vacation is all about vibrant and versatile day-to-night resort wear looks. When it comes to answering what to wear to a Cancun resort, it’s all about incorporating bright colors and prints. Check out one of the most coveted men’s 2021 summer fashion trends by adding pink into the mix. Balance out a daring pair of berry pink shorts with a white short-sleeve button-down shirt. Skip the shoes for a casual barefoot dinner in the sand. Want to give a nod to the local culture? Try a climate-friendly guayabera shirt, a lightweight shirt popular in the area. Often made of linen, they feature two vertical rows of closely sewn pleats running the length of the shirt. Pair one with hybrid shorts, and you’ll look the part of a local while chowing down on al pastor street tacos. Top it off with a straw hat to ward off those sunrays.

If you’re vacationing in the winter months, you’ll want to add layers to your packing list. December and January see the coolest temperatures of the year in the Yucatán Peninsula. Thankfully, we’re still talking mid-80s during the day. A lightweight pullover or windbreaker zip-up jacket is a perfect option for visiting ancient ruins and late night fiestas.

What to Wear to a Hawaiian Resort

Got a ticket to paradise in hand? From the killer waves of the North Shore to the lush tropics of Kauai, Hawaii is all about embracing the Aloha Spirit. Much like your Cancun inspiration, think colorful and vivid men’s resort wear. The main difference? You’ll want to welcome floral and botanical prints into your vacation wear rotation.

After you touch down, you’ll quickly find yourself on island time. Your days will be spent leisurely lounging poolside or resting in a hammock on the lanai. Stick to a beach-ready uniform of swim trunks, tank tops and flip-flops to relax in comfort. Be sure to make time for local outdoor activities like hiking to the waterfalls and volcanos. Here, you’ll want to wear your best activewear, such as sport shorts, performance T-shirts and sneakers. Look for technical fabrics that boast quick-dry, moisture-wicking and UPF coverage properties. Now you will be ready from the mauka to the makai (from the mountain to the ocean).

Is a lūʻau on your vacation schedule? Dress the part in a traditional Hawaiian shirt, also called an Aloha shirt. Long-gone is the mentality that this particular shirt is just for older men. This tropical-inspired clothing choice has seen a rebirth in the past years, becoming commonplace in men’s resort wear style. Button one up, and let it hang loose (see what we did there?) over a pair of white linen shorts. This on-point outfit will have you ready for the festivities.

Evening Resort Wear

Now that we’ve got your daytime looks dialed in, let’s talk about evening resort wear. For laid-back events, only a few tweaks take you from daytime to a night out. Swap your T-shirt for a short-sleeve button-down (extra style points for a microprint) and lace up a pair of canvas sneakers. For a casual finishing touch, try a lightweight blazer. Embrace patterns like stripes or windowpane and, as always, reach for one made of cotton or linen.

If you’re heading out to a fancy restaurant or elaborate affair, you’ll want to level up your evening resort wear. Keep it seasonal with a pair of lightweight dress pants in a neutral color like grey or khaki. A solid or subtly printed long-sleeve button-down shirt will keep you looking sharp and polished. Look for an option that boasts a summerweight fabric to offer extra breathability. Trust us, it’ll prove key when that humidity hits. A solid color sport coat and slip-on loafers will tie everything together and have you ready for any dress code. 

Need help filling your suitcase with men’s resort wear looks for your upcoming vacation? Our style experts are here to help. Take your style quiz, order a Fix and don’t forget to ask your stylist for warm-weather threads. Sit back, relax and receive five vacation-ready pieces that you can try in the comfort of your own home. As always, shipping and returns are free.

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