During last month’s Great American Hipster project, I opted to put away my flip-flops and casual clothes in place for a bit more style. I’ve always packed skinny ties in my bag (yes, even on my round-the-world trip), but there was a need for a bit more style during this vacation. My itinerary had me jumping between climates and attending a variety of events—all which would require a bit of clever packing. Here’s how I managed to maintain my hipster fashion and style while traveling North America.

I love you so much (Austin graffiti)
Sporting my Hound of the Baskervilles @OutofPrintTees t-shirt (buy it online)

Trendy t-shirts

I started my trip in Texas in August where it was a consistent 100°F or higher. I ended my trip in Boston in October where temperatures were substantially lower. That meant layering was a key part of my travel fashion. And what’s better for a bottom layer than a trendy t-shirt?

OUT OF PRINT TEES— Far and away these were the best t-shirts I had in my bag. Every day I wore my Gatsby t-shirt, I’d end up being chased down by sexy people wanting to throw their compliments at me. No joke. I spotted these t-shirts in just about every indie bookstore I visited across the USA (and I visited a lot of ’em!). Out of Print Clothing sells some of the coolest t-shirts I’ve found—especially for a book nerd like myself—but they’ve also got e-reader sleeves, hipster tote bags and phone cases.

via Kneadle

KNEADLE T-SHIRT — Okay, I was going a bit obvious with this choice but this httpster t-shirt was just so obviously cool, I knew I had to have one! It’s been a big hit with my friends who are not only internet nerds, but dorky hipsters, toos.

CHEAP, CASUAL BRANDS — It doesn’t matter how many times I seek out the most unusual and unheard of t-shirt brands, I always end up buying clothing at some of the biggest hipster fashion chains. They’re convenient and reliable, and often cheaper than indie designers. Whenever I run out of cool tees to wear on a trip, I’ll head for the nearest H&M to pick up something I know I’ll like. It might not last much longer than the trip, but at under 20€, it usually can’t be beat in a timecrunch. Other cheap, casual and cool brands I graviate toward include Jack & Jones, Primark, Zara and Topman.

sneakers trash
Disposable sneakers — via Primark

Throwaway sneakers

Most of your basic consumer, Gen-Y clothing shops sell affordable sneakers as well. They’re not going to be high quality nor will they have any support, but if you need a good-looking shoe that folds up nicely to fit into a bag, they’re hard to beat. I’ll typically buy a pair of sneakers at Primark for less than 10€ and it’ll last about a month of hardcore urban travel. The pair above lasted almost the entirety of my USA trip—serving its purpose well enough to get me into the persnickety Boston nightclubs.

Quick but formal attire

Sometimes all you need to jazz up an outfit is a few easy-to-find accessories. I’ll usually pack the following (one of each) to help turn a boring outfit into something that’ll get me into one of those obnoxiously discriminate nightclubs.

KEFFIYEH AND/OR SCARVES — Wrap a scarf or keffiyeh around your neck in the summertime, and you’re instantly “stylish.” Sure, it might be a bit of a douchey style, but if you can pull it off, why not? Keep things quirky and wear it with confidence.

SKINNY TIES — A longtime favorite of mine, skinny ties have been on my packing lists for as long as I can remember. Personally, I find them to be a rather resilient clothing option. They’re casual but trendy enough to make you stand out—an easy way to catch someone’s eye. And they take up so little luggage space, what’s the point if you don’t end up wearing them? You could always, uh, use it to tie something up if the situation arises.

VEST AND/OR SUSPENDERS — Another quick but elegant way to spruce up an outfit is to throw a pair of suspenders or a simple vest over your shirt. They won’t take up much luggage space and it’s a really simple way to add a bit of unexpected style as a tourist.

knomo laptop messenger bag (photo)
This sleek messenger bag served as the perfect travel bag to add a bit of style to my travels

Snazzy luggage

While I still have my North Face backpack with me for backpacking adventures, when I’m visiting cities or doing some urban exploration, I’d much rather have a rolling suitcase. Different luggage for different situations.

KNOMO — When looking online for some modern, cosmopolitan luggage, I stumbled across the Knomo brand. Their bags and luggage are some of the sleekest and stylish I’ve seen. The Bungo men’s messenger bag which I traveled with on my most recent trip was both sleek and stylish. It’s made from full-grain leather which I was hesitant about at first, but the bag’s canvas is made from recycled plastic bottles—so that balances out the eco-friendliness, right? My 15″ Macbook Pro fits perfectly into the laptop pouch and I don’t even need an extra sleeve for protection because of the bag’s design. One less thing to pack.

HIPSTER TOTES —  Another bag worth packing for urban trips are the hipster totes you see hanging casually off many-a-hipster’s shoulders. They’re the ones that you get for free at events and film festivals—things like the Hipster Olympics in Berlin last summer. It’s a quick and easy way to carry things around without lugging some backpack around. Or you could always go the route of the fanny pack—which I hear is hip again.

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