Travel Style Under $100

Travel Style Under $100

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Travel style is a slippery slope – of course you want to be comfortable during long flights, but where’s the line between athleisure and “just rolled out of bed”? If you don’t have tons of money to drop on all-new brand name clothes, packing can become stressful very quickly.

That’s why I turned to one of my favorite fashion/beauty bloggers and besties since high school, Chloe of Chlo and Tell. Chloe is here as your personal stylist to curate the perfect travel outfits without breaking the bank. Check out her tips for the perfect (and appropriately stylish) travel uniform:

Why I Care About My Airport Outfit (& Travel Style Inspo Under $100!)

Airport style has always been popularized by celebs and influencers, but to some, it makes no sense to put effort into an outfit that’s just going on a dirty plane. I was one of those people who would internally eye roll at anyone standing in the security line dressed for a first date, but it all started to make sense when I got the courage to ask for flight upgrades.

Over the past year or so, I finally decided to grow some boobs and walk up to the counter at my terminal to ask if there were any complimentary upgrades. The first time I ever attempted this, I looked fairly put-together in a blazer and jeans, as I was going straight to a work function. To my astonishment, I got bumped to business class (with extra leg room – holler!). The next time I tried it, it was a late night flight and I was wearing grey joggers (not cute ones) and a sweatshirt. There were no available upgrades – which I thought nothing of at the time – but then I saw the plane wasn’t full, so you tell me if that’s just a coincidence!

I soon got drunk with power and began asking for upgrades every time I flew. It worked probably about half the time, but I noticed I was much more likely to be taken seriously and bumped up when I appeared semi-presentable. Obviously, there will be times when gate agents truly don’t have anything available, and they will turn you down even if you look like a million bucks. But it’s always worth a try, and evidently, worth putting that extra effort into your appearance.

Now this doesn’t mean wearing your job interview suit or the dress you wore to meet your boyfriend’s parents – in fact, I’ve found just as much luck with (intentional) athleisure. Instead of a hoodie and pilling yoga pants, you can still be super comfy in a presentable outfit. My example below, including a cute pullover that covers the booty, camo leggings, sneakers, a hat, and a leather bag certainly doesn’t scream “runway,” but it’s actually inspired by an outfit that I was wearing when I got bumped up last fall #fieldresearch. I made sure to round up smart pieces to bring on a trip (your travel look should always be versatile for the rest of your vacay, if possible!), and I also added in some fun tech accessories. Best part? It’s all under $100. So not only could you get bumped up to first class without paying for it, but the ensemble that got you there won’t even break the bank.

Travel Outfit

Your New Travel Uniform

Grey Pullover, $99: This brand is known for being the softest, coziest fabric you’ll ever put on your body. When it comes to drafty airports and chilly flights, this warm yet chic pullover will be the perfect layering piece. Throw a leather jacket on top for even more of a put-together look.

AirPod Case, $11: After shelling out a small fortune on AirPods, you better bet I’m going to protect them with my life. I love the little pom pom keychain – both for looks and utility (never dig through your purse searching for them again)!

Black Beanie $41: For those early flights, there’s a v slim chance I’m going to do anything with my rat’s nest. I’m always reaching for a beanie or baseball hat, depending on the season, which are ideal for covering up messy hair while seeming totally intentional.

Camo Leggings, $69: The camo trend has been having a moment for a while now, and it seems like it’s here to stay. This is also a great print for traveling in case you spill en route – since your stain will be, ya know, camouflaged. 😉

Faux Leather Backpack, $48: Carry all your essentials without getting flashbacks of the middle school bus stop. I love a shoulder bag as much as the next gal, but on a long travel day with a lot to carry in my *one personal item*, ya girl’s back needs to be spared.

Camel Scarf, $22: For cold movie theaters, road trips, and airports, I love an oversized scarf that can basically become a blanket. Grab one in a neutral color that will go with everything!

Passport Case, $10: Who decided on the drab navy blue color of passports, anyway? Love the pockets, pattern options, and price of this case!

Aviator Sunnies, $65: Another early (or potentially hungover) flight necessity. Occasionally I’ve packed my sunglasses in my checked bag and always kick myself when my seatmate doesn’t put down the window during sunrise.

White Sneakers, $70: Filed under “goes with everything,” white sneakers are a packing list must. Athleisure, dresses, shorts – these are always going to be a smart item to include. I always like to wear the sneakers I’m bringing on a trip because they’re easy to slip on/off and walk in!

Apple Watch Band $15: You already wear your Apple watch on travel days to stay organized, so why not pick up a band that can go with all of your vacay outfits? I love how this rose gold one will look nice at fancy dinners, but isn’t too much for your morning beach run.

Travel Pillow, $11: Although it’s near impossible to remain cute when you fall asleep on a plane, this neck pillow will keep your snooze looking stylish.

Carry On Suitcase, $90: Hard shell to protect your prized precious cargo? Check. Spacious enough to fit everything, but still meet carry on regulations? Check. Trendy plum color? Bonus!

Is the Effort Worth Potential Upgrades?

So what do we think – this doesn’t seem like too much of a pain to throw on before you leave for the airport, does it? If you’re still wondering why your outfit would affect the airlines’ decision to upgrade you, it’s because at the end of the day, they all want to be represented well. Lest we forget #leggingsgate when those girls were told their spandex didn’t meet the dress code policy of the friends and family pass. The same holds true for any airline passengers who are “not properly clothed,” so anyone who thinks that gate agents don’t notice your #ootd is sadly mistaken.

Although I don’t condone judging others by their clothes, we all know how to look like functioning members of society – and if it helps me get upgraded to first class for free, I’m all for it.

For more fashion and beauty advice from the expert, check Chloe out at and follow her on Instagram.

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