Backpacker Chic

We’ve all seen them. Hell, we’ve all been them. Same pair of Columbia or equivalent hiking pants day after day with a t-shirt you washed in the sink. Backpacking sure isn’t glamorous, but who says we have to look like slobs? I’ve found that it is possible to look cute when traveling with the help of cheap stores like Forever 21H&M and Topshop and fabrics that don’t wrinkle or dry quickly. I’ve made some embarrassing fashion choices while traveling, but I think by now I finally have got the hang of it. Note: This post is geared more towards girls (because what do I know about mens clothing) and summer clothing, which is now on sale! Time to make a trip to the Southern Hemisphere for another summer. Potential winter post forthcoming.

Must Have Items

Little Black Dress

Cotton is preferable because you can just throw it in your bag. This one from Forever 21 ($12. 90) is great because it can be dressed up or down with something as simple as a belt. If you needed to you could also wear it with leggings or tights. I have a ton of these, my favorites being a v-neck style from Ann Taylor Loft and a spaghetti strapped one from Gap. I have worn them on airplanes (very little place to hide things, but security searches me anyway) or out to bars.

Skinny Jeans

Jeans may take up a lot of room in your backpack, but you should pack at least one pair. Skinny jeans (Forever 21, $19.80) are the most versatile, even those God awful jeggings things. I prefer dark wash because they look more professional. I didn’t bring any on a trip to Italy in 2006 (it was in May, why would I?) and they had an unexpected cold front. I had to buy a pair in Siena because I was freezing my ass off in my cute little sundresses. I wore them for years afterwards.

Leggings

I’m not going to lie. It took me a really long time to get on the leggings bandwagon. Maybe it was because I saw one too many girls wearing cameltoe style leggings and Uggs with a too-short shirt walking down the streets of Charleston. My grandmother sent me a pair in the mail one day and I can now praise their usefulness if worn correctly. I have worn them under dresses that are a little short, worn them under jeans to keep warm, worn them as pajamas in a conservative country that didn’t want me sleeping in my undies and worn them on an airplane for comfort. You can buy them pretty much everywhere (mine were some random brand so I couldn’t suggest them to you) but Heritage has these Remi Knit Leggings for $12.90. 

Shorts

Always a safe bet for summer travels, I packed one pair of black shorts and one pair of black athletic shorts. Had I planned ahead a little more, I would have either added or substituted a pair of jean shorts since they go with more. I just bought the above pair for $10 at TJ Maxx, another favorite store of mine. Don’t mind the awkward dressing room photo or unflattering top. They’re light wash and have holes in them (a little trashier than my usual taste) but I had an outfit in mind when I bought them. Plus, I can only do so much damaged to cheap pre-ripped shorts on the road. I like these from Heritage ($18.90) because they’re a little classier and are cuffed.

Easy T-Shirts

I try not to wear grubby shirts from high school on trips anymore (mostly because it is more obvious that you are a tourist) but instead wear these adorable shirts from Forever 21 and Heritage that have a more flattering neckline. I also love basic solid colored v-neck tees from Target and Gap. The one I am wearing in the picture (and pretty much every picture from this summer…) is a Forever 21 find ($12.90). Tank tops are also a no-brainer and I like the more funky designs on lightweight racerbacks. The one above is the City to City Love Tank ($8.80).

Black Flats

These are my number one, must have travel nonessential item. I have a rubbery pair from Target for $15.00 that I have worn to work and traveling all over. The toes are pretty scuffed now, but have served their purpose well. Black is the easiest way to go, but there are a lot of good options for simple, durable flats. The woven silver style ($17.99) is another great option because it is more breathable but also stays on your foot better than a sandal.

Cute Sandals
I have to thank my mom for these adorable Miss Trish for Target sandals I borrowed from her. They’re not the most comfortable shoes, but they are cute for going to a restaurant or something. Target has a great selection of cheap sandals like these Sunny Feet for $21.99. 
Toms
 
These were my go-to shoes for the entire trip. I wore them on the airplane (easy through security), on the back of an elephant and traipsing up the City Walls in Dubrovnik. They sustained some major stains, but nothing some good scrubbing couldn’t get out. I chose this pattern because they were funky, but the solid colors could go with any outfit.  Mine were the Blue Tangier ($54.00) and the ones on the left were the Morocco Vegan pattern ($54). 
Scarf

I travel with a scarf no matter the season because it can work as a shawl for a cold restaurant, a sarong at the beach, a balled up pillow on a long flight or even a small blanket if you have to stay the night. My grandmother bought me this scarf in Morocco and I have taken it on every single trip. I have no idea how much it was, but I am sure it was fairly cheap. This Urban Outfitters option is lightweight and could be paired with many outfits ($24.00). 

Headbands

The obsession with these cute flower headbands began a couple of years ago when I got one of the $20+ J Crew ones for Christmas. Since then I have cultured a collection like one from Argentina that my roommate brought me and the one above that I bought in Chiang Mai for less than a dollar. The Forever 21 headband is only $3.80, which is much closer to the prices I’ve seen overseas. It’s an easy way to dress up an outfit or to distract people from your greasy hair (which is why you see me wearing them so often). If you want something more sensible, my grandmother brought me a cool fabric one from Guatemala that I use for running or cleaning or any time I am sweating.

Non-Essentials That Didn’t Make the Cut (or the Backpack)

I know I used a lot of Forever 21 merchandise in this post, but that’s honestly where I buy a lot of clothes. If you’re reading this Forever 21, please start paying me for writing this crap. Or give these clothes to me for free. Thanks.

About Caroline

Caroline Eubanks is the founder of Caroline in the City. She's a freelance writer based in Atlanta, Georgia but also considers Charleston and Sydney home. Her past writing credits include work for Uptake, Matador, the Charleston City Paper and she is a contributor to Her Packing List.
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8 Responses to Backpacker Chic

  1. Andi says:

    Looooooove this post! I agree with everything on the list (minus the headbands, at least for me, as they give me awful headaches).

  2. Emily says:

    I totally agree! I can't do headbands with my crazy curly hair, but I ALWAYS travel with a comfy black dress, cute flats, leggings, and some Tshirts. I know some girls who are hardcore backpackers and won't bring anything cute/girly, but it's nice being able to dress up or dress down. Especially if you want to go out to a nice dinner or play some evening! And you're right–Forever 21 and H&M are perfect for this, so if you lose it or rip it, it's not a big deal.

  3. Candice says:

    Hahah, when I saw this post, "black flats" immediately popped into my head. They're like my go-to fashion piece for EVERYTHING. This is a cool niche, ya know? Being a "Backpacker Fashion Expert." lol

  4. ramblinbess says:

    I guess I am very typical then b/c I too agree with everything on this list. I love headbands but they give me a headache too.

  5. Connie says:

    I loved this post! Backpacking's a hard life and of course you want to be comfortable on those long bus/train/plane journeys, but man, let me tell you, sometimes I'm sick of seeing myself dressed as a hobo. I'm inspired by this post and I'm going to make a better effort to make myself look like a normal human being again, even as I continue to travel Asia!And, PS. I ADORE your Toms!

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