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How to Pack for a Long Weekend in Paradise

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Here are 5 must-haves you’ll want to take with you (plus some proper sunscreen, of course), before you jet off to your next sunny destination.

The hardest part of a vacation is crafting your out-of-office message. The second hardest part is figuring out what to pack. You could develop a foolproof, but monotonous, system. You could toss tons of clothes in a bag and hope they add up to enough functional outfits. You could waste hours crafting them upfront. Or you could just commit to GQ’s Three Simple Rules of Packing Simply:

  1. Limit yourself to a bag that only allows the essentials.
  2. Pack for the trip you’re going on, not the one in your head.
  3. Favor pieces that pull double duty

With this patented system in mind, here are eight getaway staples you should pack no matter what warm weather locale you’re headed to this summer. (And don’t forget the duffel bag to toss everything into.)

1. A Vacation Shirt (that You Didn’t Buy on Vacation)

You know those cheesy floral button-ups your dad, goofy uncle, and summer camp director wore when you were growing up? They’re cool again. But unlike the actual souvenir shirts those guys threw on in the warmer months, 2017’s best versions are cut slim, and the patterns are less hula girl, more hella cool.

2. A Pair of All-Day Chinos

Jeans are too damn sweaty; they make everyone else sweat on your behalf. Trousers feel as stuffy as the word itself. And while linen pants are easy-breezy when it comes to vacation life, it’s hard to find a pair that aren’t cut extra-dumpy. But somehow your favorite khakis—whether you wear ’em five days a week at the office or just for kickin’ back on Saturdays—make the transition from mainland to island. They can handle a few days of wear without a wash (maybe steer clear of sauces, though) and sharpen up your polo-shirted night-out look.

3. The One Slip-On Sneaker to Replace Them All

The slip-on sneaker is the patron saint of perfect tropical wear. It’s functional (nothing goes off-and-on faster at a TSA line or a shoreline). It’s comfortable (whether you’re walking to see some sights or just strolling to the beach). And, when slip-on sneakers come in a bold pattern like Van’s extra-classic surf’s up checkerboard, they make even a khakis-and-tee look stand out in the right way.

4. The Anti-Swim-Trunks Swim Trunks

Why pack shorts to lounge in the pool and shorts to wear around to the pool-adjacent bar when you can get you a pair that does both. Not only will they save you room in your bag, but they’ll save you time. There’s no need to go back to the room and change before lunch if the only person who knows you’re actually wearing swim trunks is you. You’re looking for swim shorts in solid natural colors and cut like your best dress pants—just a lot shorter.

5. The Best Polo Shirt You Own

Yeah, this whole vacation deal is about escaping your 9-to-5 dress code, but trust us when we say that being the best-dressed guy at the tiki bar has its advantage. A knit polo looks luxe and laid-back all at once, especially when you opt for one with a punchy graphic detail like a striped collar and cuffs.

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