Travel Hacking Your Wardrobe

Packing light and looking good isn't as simple when you're prepping for a long-term trip. But with a little help from some friends -- and the latest men's fashion trends -- we'll show you how to do both with plenty of room to spare.

Take the 'lug' out of your luggage without sacrificing style.

Packing for long trips can be a nightmare. You lay out all of your favorite clothes, open your bag, and after 10 min. of meticulously ‘Tetris-ing’ everything in, you arrive at a harsh reality: you're severely overpacked.

If I were writing this article in 2010, I might implore you to conduct a personal intervention and re-think that nightlife-appropriate swag you snuck in for an outdoors trip to Machu Picchu. Sure, you may not look AS good for those nights out in Lima or Cusco, but is the extra outfit literally worth the weight on your back?

“The most important rule to follow when packing clothes for multiple weeks of travel is to ensure each article of clothing can be worn for multiple purposes, in multiple settings, multiple times before washing..."

But fortunately for you, it's 2021, and you have the ultimate hack on your hands: “athleisure.” Before becoming the benchmark for satisfactory work-at-home attire, athleisure used to be your buddy’s lazy excuse to avoid changing between working out and going out. But more broadly, it’s the style revolution that’s dominating every major clothing brand in fashion.

After Lululemon transformed athletic wear (check out founder Chip Wilson’s fascinating story on one of our favorite podcasts, “How I Built This”), brands like FILA and Adidas have made huge comebacks predicated on composite fabrics, stylish joggers, chic sneakers, and in Adidas’s case, controversial rappers-gone-designers selling shoes not named Jordan to people, like us, who can’t afford them. (update: Kanye, "86'd")

But how does this fashion trend impact men’s travel? As the most important rule of long-term travel packing is to ensure each article of clothing can be worn for multiple purposes, in multiple settings, multiple times before washing, athleisure offers a comfortable, practical, hyper-efficient solution. And because athleisure products are both functional and stylish, your clothing will allow for more options and less concerns, no matter the occasion.

If you haven’t already invested in some of these items, be sure to pick them up prior to take-off. That way you can knock out every kind of wild experience on your bucket list and, more importantly, look damn good doing it:

Composite-Fabric Boxers

Comfort begins here. Although polyester clothing can save you a ton of room when packing and make you look 'uber svelte from zeh vaist down' it can be a HUGE source of stink, so you’ll only be able to wear something once before washing. Cotton, on the other hand, is better at battling the stench, making it an ideal, go-to fabric for boxers and underwear. For the best of both worlds, we’d recommend a composite material (like micro-modal), as 100% cotton doesn’t pack as well and takes way more time to dry. And for those of you embarking on food tours of India and Southeast Asia: always buy dark colors (we’re just going to leave it at that).

Dan does stairs... in athletic shorts with built-in compression and shoes that'll collapse conveniently in his travel bag.

Athletic Shorts (w/ compression):

A great hack I swear by to reduce the number of boxers you'll need is to snag athletic shorts with a built in compression layer. I have 2-3 pairs from Patagonia that have lasted me years and can also be used for swimming, which comes in clutch for any trek to a waterfall or along a body of water. Not only will they dry quick the added layer will mercifully reduce chaffing on the long hike back.

Kicks:

Shoes are one of the most important articles of clothing to keep in mind when you’re preparing for a trip. While having three or so pairs of shoes will certainly give you options for every activity and night out, your bag will weigh a ton, and they simply take up too much room, especially if you need hiking boots (tie them to the outside of your bag, btw).

Fortunately, fashionable, athleisure-inspired kicks have rendered this dilemma obsolete. I have a friend over at Adidas that will usually hook me up with a pair of discounted prime knits, but once those were discontinued, I found these knit runners from No Bull. They're made for workouts and light hikes, but won’t keep you out of most clubs when you hit the town. Best of all, they collapse for packing and wash easily. Also check out all-wool Allbirds. Hardly the wool of ugly sweaters' past, their products are made to last, are washer safe, and compact nicely.

Socks: A Generational Debate

It feels like every 5-10 years there is a public reckoning on mens socks. When this article was first written, no show socks had finally become accepted as a practical and stylish way to maintain the interior of your favorite shoes without looking, in shorts, as if you just arrived from the gym. Otherwise, you risk looking like a schlub from the shin down, and your unmitigated feet could be a potential Chernobyl disaster, especially in cultures, like Japan, where shoes come off.

Now a days, however, the kids can't get enough of old school, white, calf-length socks. And I'm no stranger to a fashion cycle, when it comes to packing for travel, standard white gym socks simply don't make sense. My advice: stick to the dark colors technique, and pack more no-shows than ankle-ups. If you're headed to Europe in the Spring or Summer, for example, ankles are forever in style, while white socks always look tacky and out of place.

Unless you’re planning on doing significant hiking/trekking, I wouldn’t recommend packing more than 1-2 pair of wool socks (although, in cold climates, they're nice to sleep in), and no matter the climate or purpose, I always end up wearing no-show socks with a pair of athletic shoes. Invest in some durable, low-cut socks, and you’ll be good to go. If you're reading this article having already embarked, you can always find cheap socks that’ll do the trick in areas of Asia or South America, saving you a few bucks for better things on the road.

Joggers:

There was a time where men might feel less manly for coughing up $100+ on a pair of Lululemon pants. Regrettably, I was one of those men.

Why are they worth it? Well, not only do I still have the same pair of joggers three years later, I also wear them about 50% of my time when I’m traveling. In a pre-COVID trip to Bangkok, I wore them on my flight, kept them on as I explored the city for the day, and after a quick shower, I rocked them again when we went out to a few clubs and rooftops that night. Gross? Nay. Confident AND economical? Absolutely. I always recommend getting a pair with zipper pockets as it’ll reduce the chance of losing something important or getting pickpocketed in certain areas of the globe.

Light Outer Layer:

No matter what climate you’re headed to, having a light outer layer is going to come in handy. In cold weather, use it as a layer. In warmer weather, you’ll find it handy for airplanes, airport lounges, or when you finally find a gloriously air-conditioned hostel. Also keep in mind that in cities at high-altitude, like Quito or Mexico City, you’ll experience serious temperature swings after nightfall. Having something that's light, long-sleeved, looks clean, and fits in a day bag is just about as clutch as a clothing item gets.

Colors:

Expanding upon the boxer segment, when you’re picking out what products you’re going to buy, I almost always stick to darker colors. This in no way is a reflection of my dark, tortured soul, but more so an intentional strategy towards practicality and flexibility. If you’re headed to the Mediterranean, by all means pack a white linen shirt and bright, fitted slacks. And if there’s an article of clothing you know you’ll wear all the time, pack that too. However, darker colors will almost always make a casual outfit look nicer in the evenings, and stains, though inevitable, won't show as much as they do on lighter hues. I’m sure you’d love to pack that neon green or robin’s-egg blue jacket that kills it on the weekends back at home, but you don’t need it, and it’ll be wrinkled and creased when you actually want to wear it.

Formal:

If I absolutely must pack a sport coat or suit for a particular trip, rather than meticulously folding it to reduce wrinkles and creases, I’ll typically wear it during travel and lay it on top of my luggage in an overhead compartment. Ignore anyone who ever says you shouldn’t look good in transit: there was a time when travel was a luxury, and after the year we've all had, travel should be savored and celebrated with style and flare.

So, look the part. I've met plenty of fascinating people in transit, and nothing says “I’m the kind of person who knows what they’re doing, where we're going, and what we should drink when we get there,” more than a man in uniform.

Conclusion:

Look -- there's no universal way to pack, and your destination is always going to be the ultimate dictator of what should live in your backpack or suitcase. However, if you embrace the athleisure wave, predict what you'll be buying when you get there (check the tag, buddy, it's probably from Southeast Asia), reduce your shoe count, and focus on items that can be worn both in a city and layered during a trek, you'll be traveling light and looking good for every kind of stop on the itinerary.