Resort 2021 Travel Style Out

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2020 was certainly not the year to globetrot. With some countries restricting admission to foreigners, travel was at times virtually impossible.  If you are a savvy traveler who plans ahead, you may have postponed your 2020 trips to 2021. This has given you more time to decide the details of your trip—what sites to see, where to eat, and what outfits to wear.

In the fashion season cycle, “resort season” comes right after the holiday season, and leads into the spring. This is the time when people leave their cold weather residence and vacation in a warmer climate until their hometown climate is suitable for their return. Some travel the world to locales like South America, the Caribbean, or cruising around the Mediterranean. Others use this time to extend their holiday vacation and take a small cross-country trip.

No matter whether you travel across an ocean, across the country, or across the state, you’ll want to look your best while on vacation. We’ve created 6 wonderful looks for trips around the world (or around town) so you remain chic while hitting the streets.

Caftan: MC2 Saint Barth $162
Long Shorts: Wins $95
Slippers: Blue Bird Shoes $175
Sunglasses: Chimi $149
Bracelet: Swarovski $99
Bag: The Jacksons $105

Mediterranean Cruise

Everyone dreams of taking a Mediterranean cruise. Marbella. Nice. Monaco. Venice. Athens. Some of the most luxe ports in the world. Part of the fun of cruising is disembarking and exploring the coastal towns. No one will mistake you for a local in this outfit. But when you’re this chic, you’re never out of place.

Coat: Goldbergh $598
Pants: Peak Performance $429
Gloves: Rossingnol $120
Sunglasses: Italia Independent $201
Bag: Off-White $592
Boots: Moncler $695

Skiing in Breckenridge, Colorado

Not everyone wants warm weather. And not everyone wants to travel to Europe to hit the slopes. Breckenridge, Colorado is one of the most ideal ski towns in the United States. Brave a black diamond run, if you dare. But if you just want to take it easy, pull up to the toboggan slopes in this ensemble, and then relax by the campfire with a hot toddy.

Vest: Philosophy di Lore $391
Turtleneck: Balenciaga $495
Jeans: D2Squared $720
Boots: Chloe $700
Sunglasses: Garrett Leight $336
Bag: Golden Goose $578

Southwestern Dude Ranch

Sometimes a city slicker wants a change of scenery. If the rustic life is for you, head to a dude ranch. But don’t leave all of your big city sensibilities at home. You don’t have to look like a ranch hand while down on the farm. Let your wardrobe say “I’m here to vibe, not to work.”

Bathing suit: Versace $650
Sarong: Amir Slama $476
Shoes: Manolo Blahnik $975
Sunglasses: Sestini $420
Necklace: Monies $1,134
Bag: Valentino $1,116

Destination Trip – Port Antonio, Jamaica

If you want isolation in close proximity to great food, music, and culture, there’s no place like the 5-star resort Trident Villas in Port Antonio, Jamaica. It’s so serene that you may not want to go home. Look your best as you live your best life alongside your private infinity pool or the private beach. If you want to head to town, put on your sarong and go. Simple, yes, but simple can also be sexy.

Jacket: Alexis $682
Shirt: Natori $174
Pants: Sportmax $525
Head scarf: Emilio Pucci $294
Bag: Mansur Gavriel $495
Shoes: Stella McCartney $560

Cultural Trip – Petra, Jordan

Full of history (dating back as far as 7,000 BC), Petra is one of the most reverential cities in Jordan. When visiting, most people respect the Jordanian culture and dress accordingly. The temperature can rise and fall quickly, so it’s smart to wear layers.  This outfit provides a mix of layering and modesty for you to enjoy the sites with the respect that they deserve.

Loungewear set: Rails $89
Robe: Vivis $50
Socks: Marni $51
Slippers: Emporio Armani $70
Necklace: Kurshuni $39
Sleep mask: Morgan Lane $110


Sometimes the best vacation is a staycation. Put your feet up and relax in the confines of your own space.

No packed airplanes. No pricey hotels. No language barriers. The most you have to travel is from your bed to the kitchen to the couch—I doubt you’ll get lost. For an extra assurance of peace, put your phone on do not disturb. Enjoy.

—Carl Ayers

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