THE BLOG
07/01/2014 02:27 pm ET | Updated Aug 31, 2014

OTP's Guide to Swagger on the Road

Make like the hippies, beatniks, rastas, and punks and pioneer your own street style.
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Photo by: Angelo GonzÁlez

That popped-collar polo and pre-distressed pair of khaki shorts make you look like you were stamped out from the same douche-shaped cookie cutter as the rest of the uninspired masses. Street style is about taste-making, not trend-following. Think about it, who would you rather approach: the person whose clothes scream "I give a thousand fucks what you think of me" or the one whose outfit shrugs confidently and says "this is me and I look damn gooood"?

Flash Da Cash
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Photo by: Kheel Center

Escape the ever-present, teenager-choked, throwaway-fashion-tragedy-clusterfuck outlets by dipping into the independent designers' studios--every city's got 'em. They're usually the size of a closet and only have a couple of rolling racks of clothes to pick through, but what's there is quality. The prices can be a little balk-inducing, but if you've ever taken the time to design, knit, sew, or fabricate something yourself, you know that shit takes time and money. The only reason you can get a sweater for $14.99 at a megastore is because underpaid workers are being exploited at every stage of their manufacturing. If these workers were properly compensated, the final product would cost what the solitary artist struggling away in his studio is charging. Shell out for the good stuff and remember these pieces are investments--they wear better and longer than the polyester, rash-inducing, chemical-soaked crap that gets shipped in from parts unknown. Plus, you're fueling the creative economy and throwing a bone to a starving local artist. Rack up some good karma while upping your fuckability quotient.

Slumming It
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Photo by: News Oresund

If you're cheap--and we know you are--flea markets, craft fairs, and thrift stores are other caches of street style gold. Finding sartorial treasure in these kinds of places takes a bit of persistence and a measure of bravery in confronting unidentifiable odors. Put aside your squeamishness and think of it this way: poking through vintage clothes to find something that speaks to you echoes a lot of the reasons and rewards behind travel. There's a sense of adventure in plumbing the unknown depths of the discount bin, a thrill in embracing unfamiliar garments that once dangled in foreign closets, an enlightenment and continuity in seizing upon the same vintage Adidas jacket that some Casanova from the 70s used as a chick magnet.

The Devil is in the Details
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Photo by: Edoardo Costa

Proper accessorizing can make the difference between looking busted and looking hawt. Pay attention to your watch, hat, sunglasses, shoes, and belt buckle. Handkerchiefs are the renaissance men of fashion accessories--they do everything. Tie one on your head or neck to protect against the sun and up your swagger factor. Hang one out of a pocket or wrap one around your wrist. Using accessories in ways that go beyond their original intention (using a necktie as a belt, perhaps?) also scores you some fashion maverick points and saves room in your backpack.

Street Style 101
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Photo by: Juanjo Zanabria Masaveu

Now that your closet/backpack is stuffed with cool clothes, how do you assemble them to make a look that would earn David Bowie's nod of approval? Experiment. After all, the essence of street style is individuality and the only difference between an outfit that's hot and an outfit that's a hot mess is the confidence of the wearer. That said, here are some general tips to get you started thinking outside the mainstream box. Go for contrast and layers. Incorporating different kinds of fabric into an outfit lends intrigue and tactility to your look. Rocking contrasting colors also makes you more ogle-worthy. Throw some prints around--dare to make someone seasick just by looking at you.

At the end of the day, street style isn't about being flashy or crossing your fingers hoping to get snapped by a street photog. It's about using the swaths of fabric that decency dictates you must wear to cover your shameful naughty bits to express what you're all about. It's about extending your authenticity to every aspect of the way you inhabit the world--down to the fit of your pants and the swing of the chain around your neck. Traveling affords you the opportunity to switch up your style with every destination you visit until you find your fashion identity.

Written by: Rachel Dunlop