5 Editors, 5 Travel Outfits Under $100

Your suitcase might be organized, itemized, and systemized to the max, but if you're still traveling in pajama pants and that high school sweatshirt, we need to have a talk. We know that jet-setting isn't as much of a luxury pastime as it used to be, but there's no reason for your first outfit in a new locale to be something you also wore the last time you battled a stomach flu. Flying, taking a long bus ride, or hopping onto a train might not have the same glamour associated with them as they did in our grandparents' time, but that's no excuse to bust out the fleece onesies.
That said, you also shouldn't be submitting yourself to discomfort. Just say no to pinching pants that cut off circulation, itchy collars that grow pricklier with each hour, and stiff fabrics that won't let you curl up. Flying the cozy and stylish way is totally possible — and you don't have to shell out a million dollars to do it. As proof, we sent five of our editors to five neighborhood mall brands to create a perfect, polished travel outfit for under $100. So, click through to see how (and if!) they pulled it off.
CheapChallenge_AnniePhotographed by Amelia Alpaugh.
Forever21 AC/DC Crop Top, $12.80, available at Forever21; Forever21 Sleek Linen Jacket, $32.80, available at Forever21; Forever21 Modernist Faux Leather Satchel, $24.80, available at Forever21; Forever21 Elephant-Print Pajama Pants, $22.80, available in-store at Forever21.
Annie Georgia Greenberg, style editor
"My search for the ideal travel outfit stopped as soon as I saw these pants at Forever 21. They're everything I seek in something I want to sport on a plane: comfortable, good-looking, and wearable in any climate. I especially love the idea of donning printed pants with a rocker T-shirt. This linen jacket finished off the outfit perfectly because it's lightweight (read: easy to layer) and has pockets for passports. Or, you know, snacks."
CheapChallenge_ConniePhotographed by Amelia Alpaugh.
Uniqlo Women Drape Bottoms, $14.90, available at Uniqlo; Uniqlo Modal Color Stole, $12.90, available at Uniqlo; Uniqlo Women Sleeveless Dress, $19.90, available at Uniqlo; Uniqlo Women Printed Pocketable Parka, $29.90, available at Uniqlo; Uniqlo Jacquard Short Socks, $12.90, available at Uniqlo.
Connie Wang, style director
"My whole MO for travel outfits isn't about comfort; it's about saving space in my suitcase. That's why you'll usually see me at the airport wearing the most space-inefficient things I've brought with me, like giant platform sandals, leather pants, and all my sweaters. However, over the years, I've figured out a mix of packing efficiency and in-seat lounge-ability that works for me, and Uniqlo really helped me achieve both."
"I'm all about stretchy materials when I'm on vacation — but in punched-up styles. So, this patterned tank dress and these silky drawstring sweatpants together make the perfect dressed-up pajama. I always freeze on flights, too, so a lightweight jacket and a scarf are imperative (no matter how hot the destination I'm traveling to is). Uniqlo, unfortunately, wasn't stocking any bags or shoes, so I went with my real-deal go-tos: beat-up Converse so loose I can slip them on in three seconds and zip through security, and a roomy leather tote from Cuyana. (I tie up the handles so nothing slips out when I place it below the seat in front of me.)"
CheapChallenge_MarissaPhotographed by Amelia Alpaugh.
American Eagle Straw & Jelly Tote, $14.99, available at American Eagle; American Eagle Mens Tank Top, $10, available at American Eagle; American Eagle Slip-on Sneaker, $24.95, available at American Eagle; American Eagle Reverse Ribbed Cardigan, $19.99, available at American Eagle; American Eagle Boy Jean Crop, $49.95, available at American Eagle.
Marissa Rosenblum, market director
"I'll cut to the chase and put something out there right away: I found a Cheap Challenge loophole. But, before you cry foul, I must admit that my rule-bending, money-saving ways are actually an excellent shopping tip cloaked in the guise of TOTAL CHEAP CHALLENGE DOMINATION. (Sorry, Connie, Annie, Gina, and Leeann.) After chitchatting with the sweet, helpful team of shopgirls at the Brooklyn Fulton Mall location of American Eagle, I was tipped off to the promo the store was currently running: $30 off when you spend $100 or more if you signed up for the AE Rewards card that day. I am officially the proud owner of one AE Rewards card."
"Now that my money-saving strategy is out, on to the outfit! I knew that I wanted something to cover my legs, because I think we all know the heebie-jeebies one can get when bare skin encounters a weird, scratchy patch of airplane seat. So, I headed straight to the jeans section. I was surprised at how many AE jeans actually fit me. I'm petite but curvy. I have thighs and a butt and hips that don't usually fit into junior-size clothing. But, while some of the jeans were cut way low, there were lots of styles that worked on my curves. A few were labeled as high-waisted, and the new "boy style" pair I purchased were shockingly woman-body friendly. The men's tank was a total score at $10, and its large armholes and loose body make it double as a beach cover-up. Lastly, the slip-on sneakers are just plain rad. The fluoro tropical print makes me feel like I'm already on vacation, and the practicality of a comfy sneaker for airport-security-to-gate sprinting ensures I get to my destination with time to spare for a Starbucks detour."
CheapChallenge_Gina 2Photographed by Amelia Alpaugh.

Old Navy Men's Graphic Baseball Caps, $10, available at Old Navy; Old Navy Women's Cross-Front Jersey Dress
$29.94, available at Old Navy; Old Navy Women's Cropped Denim Jacket
$29.94, available at Old Navy; Old Navy Women's Zip-Pocket Tote
$29.94, available at Old Navy.

Gina Marinelli, associate fashion features editor
"When it comes to traveling, I'm usually guilty of over-packing. But, as for what I wear during the trek, that's when I seriously streamline things. It's typically something multifunctional and sneakily comfortable, and it can easily be worn again in a different variation once I arrive at my destination. Thankfully, Old Navy was fully stocked with these cozy maxi-dresses that will double up as a blanket for my legs when I get chilly mid-flight or drive (which I always do). Another plus: They can be styled completely differently for dinner, a day on the beach, or a morning stroll through the local flea markets. I was also able to score a cropped denim jacket — another spring travel essential — and a roomy tote that can hold my wallet, passport, and a few magazines for the road. Finally, I scooped up this baseball hat from the men's department. It adds a sporty touch to the ensemble and also saves me from having to worry about what my hair looks like when I'm trying to remember if I packed my contact lenses and toothbrush. And, I'm proud to report that I stayed within my $100 budget."
CheapChallenge_LeeannPhotographed by Amelia Alpaugh.
Gap Stripe Roll-Sleeve Henley Top, $54.95, available at Gap; Gap 1969 Real Straight Jeans, $69.95, available at Gap.
Leeann Duggan, style features editor
"I had two main learnings from this Cheap Challenge: First, $100 doesn't go quite as far at Gap as I'd hoped. Most shirts and denim start around $50, and the store I shopped had a small sale section that, for me, didn't turn up any gems. Sadly, that meant I had no money left over to play with the colorful striped scarves, pointy flats, and cool camo jackets that caught my eye (and could have doubled as travel pillows)."
"My second finding was that Gap's basics — while a little pricier than, say, F21 or Uniqlo — are so worth investing in again. The easy, tunic-y fit of this henley makes me feel like I'm wearing the world's most chic pajama top, and I haven't found denim this flattering for under $100 in a long time. (Non-stretchy yet still comfy is a BIG find for me.) I blatantly went over budget and had to supplement with my own jacket, hat, and shoes. But, the loose-top-and-skinny-jean combo is a classic that'll serve me well on travel days and beyond. And, after 10 years of flirting with the newer, cheaper brands on the block, I'm really into Gap again."

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