Backpacking in Style: How to Look Less Like a Hobo

Being mistaken for a homeless vagabond is a professional hazard when you’re a broke ass backpacker. Granted: you’re lugging everything that matters on your back, the crowded hostel only has one bathroom, and you’re too cheap for a haircut. But you don’t have to look like a hobo (or worse, an obnoxious American). Check out OTP's tips on how to pack it in style and stretch the shit out of your meager wardrobe.

You’re effortlessly sexy, sure, but no one looks good in zip-off cargos. It doesn’t matter if they’re worn as shorts, capris, or pants—you’re going to look like a Disneyworld tourist if you’re using them for anything but extreme hiking. Instead, pack a pair of lightweight jeans—perfect for exploring the city and blending into the crowd (roll them up or chop off the bottom and you've got shorts). Chinos work if you’re too fancypants for regular pants, and go ahead and keep some quick-dry cargo shorts if you think you’ll end up on a beach. If you absolutely just can’t leave home without some zip-off atrocity, Eddie Bauer makes a good pair if you’re a dude and chicks dig the Prana version.

A T-shirt may be the most basic article of casual clothing, but it doesn’t have to be worn typically. Channel your inner sorority girl and get creative. In the summer months, cut the long off your long-sleeved Ts, and if you’re feeling particularly hot, turn it into a tank. If you’re going risqué, bare that pack-sexy midriff by cutting a few inches off the bottom. (This look is not for everyone.) The extra strips can be used for headbands, scarves, or a tourniquet if you need to amputate a limb. Extra long t-shirts are great for women ‘cause they triple as a belted t-shirt dress, a nightgown, and a swimsuit cover-up sans the belt.

OTP Tip: T-shirts are cool as t-shirts for guys. Please leave the sleeves on your t-shirts fellas; no matter how ripped your biceps are, cut-off tanks make you look like a Village Person.

Since a long backpacking trip usually means different seasons and climates, layer-able clothes are your best bet for tackling weather changes. Giant down coats are impractical, so opt for a windbreaker with solid insulation instead. East Mountain Sports and Land’s End offer a cheaper alternative to super pricey North Face jackets. Layer a few cotton or knit Ts over some inexpensive REI-brand lightweight long underwear. Flannel shirts are great for wearing over t-shirts in cold weather, and for adding that sexy lumberjack edge. For girls, a non-chunky cardigan will keep you warm in cooler climates and make you feel like a girl, even if you haven’t shaved (or bathed) in a while.

OTP Tip: Websites like CampmorREI, and Sierra Trading Post offer discount deals on travel clothes like these. You can also sell and buy clothes at thrift stores while traveling through more developed countries.

Having to shoulder your entire wardrobe long-term means limiting your outfits to just the basics. To keep it interesting, sass up with some simple accessories. Ray-ban Wayfarers (or the much cheaper knockoff Faywarers—found at any Buffalo Exchange or market in Southeast Asia) make any outfit instantly cool and are perfect for hiding your hangover.  Other must-have accessories are hats (like fedoras or newsboy caps) for those bad-hair days. For the ladies, scarves are a snazzy addition which can also be used as headbands, shawls, bracelets, belts or sarongs.

People don’t usually pay much attention to shoes, but when you’ve got some hideous velcroed foamy sandals strapped to your feet (100 extra dorky points if you're wearing socks), it’s all they’ll be staring at. If you’re serious about sandals, upgrade to the sturdier, comfier, and slightly better-looking Chacos instead. Crocs are great for backpacking too and come in a bunch of surprisingly stylish designs—and you CAN wear these with socks without looking like a tool. If you’re a foot-conscious lady with janky un-pedicured backpacker toes, invest in a pair of  Mary Janes.

There’s a reason trendy Europeans and New Yorkers wear black all the time—it looks good on everyone. Not only will you look skinner, but you’ll have an easier time mixing and matching. Since you won’t be doing much laundry and will be eating on the go, it’s a bonus that dark clothes hide dirt and food stains. Throw in some colorful accessories to not look like a blood-sucking vampire. To avoid increased amounts of BO, choose stuff made of cotton, silk or linen instead of synthetics to let some fresh air circulate.

Dressing like the locals is great if you can rock it like they do, but sporting a flamboyant poncho in Peruvian sun or a cone-shaped straw hat at a Vietnamese bar gives you that loser look. There’s a distinction between souvenirs and local styles. You probably don’t want the extra weight anyway. Be a practical fashionista; go for subtler items that won’t be obsolete back home—like non-white linen pants from Greece or a basic leather jacket from Argentina.

With your giant backpack and traveler’s threads, you’re already going to look conspicuous. By dressing like a hobo or typical tourist, you’ll only confirm the theory that most American backpackers are either hipster wannabes or orientalist consumers with a bad sense of style. Follow these fashion guidelines and avoid being mistaken for a smelly expat gutter punk (you'll get more money busking when you look good anyway).