One thing I’ve learned about myself over the years is I love picking out my travel outfit, sometimes even days in advance. The thrill of preparing for the trip is eclipsed only by the trip itself, and I find immense satisfaction in settling into my airplane seat knowing I’m as comfy as possible while still holding onto a sliver of my personal style. If you’re not like me, and tend to leave these preparations until the night before or, even worse, the very last minute, you may wish you had some help in putting together the perfect outfit for any trip — and lucky for you, I’m here to help. 

Whether you’re a casual traveler who's drawn to cozy, oversized fits, or a jetsetter that likes to look polished and sleek while still leaning into comfort, I’ve handpicked five winter-ready outfits you’re sure to love. From slouchy cardigans to fleece-lined leggings, there’s something for everyone, and as an added bonus, every outfit comes out to under $100. Happy shopping!

Look 1

• Fixmatti Women’s Knit 2-piece Sweatsuit, $48 with on-site coupon (originally $53)
• Kidmi Women’s Suede Clogs, $36 with on-site coupon (originally $50)
• Ayieyill Corduroy Tote Bag, $10

This cozy outfit is somehow both effortlessly cool and endlessly comfortable — plus it’s stylish enough that you’re likely to reach for it throughout the duration of your trip, no matter what’s on the agenda. The Fixmatti Women’s Knit 2-piece Sweatsuit is the perfect outfit base since it can be worn together or styled separately, but the relaxed fit of each piece makes them uniquely well-suited for helping you settle into a long flight while still feeling confident that you look great. 

The best-selling Kidmi Women’s Suede Clogs are easy to slip on and off (and on sale for just $36), making them a brilliant asset for rushing through TSA without being encumbered by laces, and it certainly doesn’t hurt that they’re ultra-supportive with deep heel cups and plush cushioning. Add the Ayieyill Corduroy Tote Bag as your personal item, and you’ve created a wearable yet pulled-together airport outfit for just $94.

Look 2

• Baleaf Long-sleeve Workout Top, $20 (originally $26)
• Baleaf Women’s Hiking Pants, $38 (originally $56)
• Adidas Women’s Cloudfoam Pure Sneakers, $40 (originally $75)

If you’re drawn to sweat-wicking fabrics and leaning into the functionality of your outfits, this sport set is sure to pique your interest — and altogether it adds up to $98. The Baleaf Women’s Hiking Pants are a fan-favorite for a reason with a breathable, adjustable elastic waistband and a multitude of handy pockets, so you’ll be happy to have worn them on your flight if you like keeping snacks and other essentials easily accessible without extra baggage.

Meanwhile, the Baleaf Long-sleeve Workout Top will keep you warm all day while the quick-dry fabric is ideal if the airplane cabin isn’t adequately air-conditioned. Top the outfit off with a functional and lightweight pair of Adidas Women’s Cloudfoam Pure Sneakers, and you’ll be ready to run through the airport to make your flight without breaking a sweat (or at least cooling off quickly if you do). 

Look 3

• Copyleaf Women’s Flare Yoga Pants, $20 
• Lillusory Women’s Oversized Turtleneck Sweater, $46 (originally $58)
• Soda Pilot Women’s Lug Sole Chelsea Booties, $31 (originally $40)

Believe it or not, it’s not impossible to build a travel outfit that’s both cute and comfortable, and this combo of yoga pants and a turtleneck sweater is a testament to that fact. The criss-cross waistline of the Copyleaf Women’s Flare Yoga Pants makes them far more flattering than other picks, while the blend of polyester and spandex creates a forgiving finish. While the pants are casual, they pair well with the Lillusory Women’s Oversized Turtleneck Sweater that instantly dresses up the look for $46. And if you’re really trying to level-up your airport style, rather than grabbing a pair of sneakers, instead opt for this versatile pair of Soda Pilot Women’s Lug Sole Chelsea Booties while they’re available for only $31.

Look 4

• Baleaf Women’s Fleece-lined Leggings, $34
• Trendy Queen Women’s Oversized Hoodie, $33 with on-site coupon (originally $53)
• Zizor Women’s Cozy Short Boots, $32

Travelers looking to maximize their comfort while flying likely want to show up to the airport in an outfit that supports this goal, and nothing does that better than an oversized sweatshirt and leggings combo. The Baleaf Women’s Fleece-lined Leggings are one of the best selections for winter thanks to their thermal lining, so if you find yourself getting cold easily, these are a must-have addition to your closet. 

And since a good travel outfit is built by having the right layers on hand, the Trendy Queen Women’s Oversized Hoodie will do just the trick while it’s on sale for $33. The baggy fit is casual and cool, plus, since it comes in neutral colors you’ll be able to style it endlessly throughout your trip. Top of the outfit with the faux fur-lined Zizor Women’s Cozy Short Boots and you’ll be ready to take on any weather that comes your way. 

Look 5

• Ueu Women’s Casual Loose Wide Leg Pants, $25 with on-site coupon (originally $29)
• Urban CoCo Women’s Crewneck Slim Fitted T-shirt, $20 (originally $26)
• Merokeety Women’s Batwing Cardigan, $34 with on-site coupon (originally $52)

Flowy pants are practically made for traveling in, which is exactly why the Ueu Women’s Casual Loose Wide Leg Pants are the perfect base for this versatile airport outfit. If you struggle with finding the ideal temperature while flying, an oversized cardigan is an excellent choice since it’s easy to slip on and off, and the Merokeety Women’s Batwing Cardigan is so beautiful that you’ll even be able to style it numerous ways throughout your vacation. And since you can never go wrong with having a simple white T-shirt on hand, the Urban CoCo Women’s Crewneck Slim Fitted T-shirt is a must-have at $20 that will work as a flattering base layer day after day. 

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