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Resort Wear Buyer's Guide

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man walks in beautiful tropical resort

The holidays are over, and now instead of dreaming about presents under the tree, you’re thinking about how to escape the cold winter weather. While you’re booking your next flight to someplace tropical with white sandy beaches and crystal clear blue water, we’re here to help you plan your days once you reach the resort. 


smiling african american man relaxes on steps on a tropical beach

Day 1: Beach Day

It’s day one. You’ve finally gotten everything unpacked, slept off the flight, and are ready to start enjoying your trip. Spend the day floating around in the infinity pool with a cocktail, or take a dip in the ocean before tanning on the beach. Kick back in your Sandbar Swim Trunks with your toes in the sand and a cold drink in your hand. Don’t forget your sunscreen and flip flops!


Man with back to camera looks out over Caribbean water

Day 2: Sightseeing/Adventure Day

Now that you spent the first day getting a nice tan and catching up on some much-needed R&R, it’s time to explore the area. Go deep sea fishing for pelagic fish, hike to historic ruins, or maybe grab a bus tour of the island, the options are endless! While doing so, make sure you’re sightseeing in style AND comfort with a pair of Buccaneer Cargo Shorts and a Suntek Hoodie for added sun protection.


Man and woman look lovingly at one another on tropical island

Day 3: Fancy Dinner

Tonight, it’s time to indulge in all the culinary offerings your resort has available. From tropically tantalizing cocktails to fine dining experiences you’ll be talking about for the next decade, go all out! Don your favorite Madda Fella linen shirt with a pop of print and linen pants for an evening of fun and delicious foods while showing off a little personality. Roll up the pants before taking a stroll on the beach after dinner.


man and woman stand in front of a bright pink doorway

Day 4: Casual Lunch & Shopping Day

Today’s the day to pick up souvenirs for the family and to help remind you of all the fun memories you made while here. Stroll around the town, checking out local shops and unique places to eat for lunch*. Wear a Bayside Henley and Oxford Cross Dye Roll Up Pant to keep it cool and casual.

*Tip: Ask some of the locals where they like to eat and which tourist traps to avoid for a more cultural experience. 


laughing man enjoying tropical resort


Every Day: Tiki Bar 

If the swim-up bar isn’t available, you’ll be found at the nearest tiki bar enjoying appetizers and delicious cocktails. Relax under a shady thatched roof in a bright and tropical patterned Camp Shirt and a pair of Truman Linen Shorts. Add a fruit-filled drink and you’ll look at ease yet ready to party when the occasion arises.

No matter where you go to escape the everyday, we’ll be there to make sure you’ve got the right apparel for wherever the day takes you.

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