10 Essentials to Pack for a Mid-Winter Vacation

Image via Complex Original

Where to: Napa Valley, Calif.

Preparation for your trip to beautiful Napa Valley to whet your whistle and refine your palette on some delicious vino needs to be calculated. It’s not just about the tastings; it’s about bringing home copious bottles. And a roomy bag that can hold your bottle—or five—will be handier than you can even imagine. It will also prevent you from losing them when you’re a little tipsy.

Where to: Panama City, Panama

Sunglasses serve multiple purposes. Sure, they are definitely needed to protect your oculars as you’re soaking up the sun on the beach. But the day after a rough night, even if it’s just a wee bit sunny outside? As Kanye says, “sunglasses and Advil” are one hell of a cure. Oh, and please believe these will also shield you from suspicion as you check out all the fine honey-doo-wops without appearing like you’re actively trying to stare into their souls.

Where to: Through security check

LOL if you’re that guy traveling who needs to untie his shoes. Are you a newbie? No. This isn’t your first rodeo. But you also aren’t willing to sacrifice any style points to look like that guy who wears the neck pillow around the entire airport. Rock a pair of Vans slip-ons or Birkenstock Londons through the security check, ready to slip off and toss into the bin and back on before the TSA agent can ask you, “Is this your bag, sir?”

Where to: Aspen, Colo.

Planning to ski while you’re in Colorado and actually going skiing while you’re in Colorado are two completely different things. It doesn’t mean you can’t prepare for both in one fell swoop, right? A good technical jacket from brands like Isaora, Acronym, or Stone Island offer you the style you need to look the part, but can also act as a protective layer from the elements and the inevitable crash and burn you will be experiencing should you go through with it.

Where to: Stuck in the airport

Oh, that’s cute. You thought you were going to get out of this hellish weather without any incidents. Your naivety is concerning, but it can all be redeemed if you indubiously remembered to bring a nice, warm wool blanket juuuuust in case the plane was too cold or you got stuck in the airport. A Pendleton or Woolrich blanket in the design of your stylish aesthetic is cool figuratively, but toasty warm, literally. Hell, if you had enough dough to pick up Faribault Woolen Mills’ collab with Supreme, you may be able to score some hypebeast, sneaker-wearing chick who wants to snuggle up in Terminal C.

Where to: Europe

You’re taking a couple weeks off to backpack through Europe. It’s not quite the escape from all the cold, but it is truly an escape from the misery. And as you make your way through all of the historic, beautiful cities, you are going to be moving—a lot. So much so that a pair of denim is just not going to cut it. A comfortable, stylish pair of sweats will become your best friend. They’ll allow you to move freely and leave you unrestricted, but a really good pair won’t look too “casual” either. Now we’re not saying you should walk through the Louvre in them, but traveling 200-plus miles to get there? Don’t be cute. Well, be cute in some good sweatpants.

Where to: Anywhere

If you don’t have a decent pair of headphones with you when you travel, you are performing the definition of a brick. Sure, bringing along the headphones you got with your iPhone is fine, but they don’t have quite the same capabilities that some of the better ones on the market might have. Bluetooth so you can go wireless. Noise-cancelling so you can literally drown out every single person who tries to strike up a conversation with you. Or bass-pounding, highly accurate headphones will give you that clear sound those freebies can’t. To be caught traveling without headphones at all though? Not only is it a crime against your style, it’s a crime against your sanity.

Where to: The Bahamas

The escape has finally come. You have been pining to get out and visit the beautiful island paradise of the Bahamas. You obviously planned on packing a pair of swim trunks or two, but it’s time to drop the baggy monstrosities that go way below your knees and have 12 pockets and grab a slim pair that sit right above your knee and make you look like an adult.

Where to: Multiple layovers

You’ve lost clothing items. You’ve had bags completely rip in half. It’s all due to the poor treatment they are given while under your flight to your final destination. Your luggage doesn’t have to sustain such a beating, and you don’t have to either. Invest in proper aluminum luggage that can withstand the tests of time and the inevitable beat-down of multiple layovers. Rimowa makes premium luggage that could survive an A-bomb and still keep all your goodies fresh. Of course, you will likely perish, but your legacy will live on.

Where to: Northern borders of China

It has been a dream to visit the Great Wall of China. And while you don’t get to do it whilst riding on the back of your bodyguard, Bieber-style, you do get to experience it in all its glory with a premium camera to capture every moment. But your style won’t allow you to keep that regular ol’ Canon strap on it. Nope. You vouch for a more stylish accessory, adding a high-quality, fashion-relevant strap to your camera that is catamount to fulfilling your life’s complete synergy. Oh, and I guess the pictures are pretty important too, but whatever.