13 Oversized Airport Outfit Ideas for Trendy Comfort

Okay, real talk: airport outfits are basically an art form at this point. You need to look cute enough for the inevitable airport selfie, but also be ready to survive a six-hour flight without questioning all your life choices. Enter the oversized outfit—your golden ticket to looking effortlessly chic while feeling like you’re basically wearing pajamas. Because honestly, who wants to be that person squirming in skinny jeans at 30,000 feet? Not me, and definitely not you.

The beauty of oversized pieces is that they give you that cool, undone vibe without actually looking undone. Think baggy hoodies, roomy trousers, and sweaters that could double as blankets. These looks are perfect for layering, moving through security like a boss, and still turning heads at baggage claim. Whether you’re jetting off for a weekend getaway or a business trip, these 13 outfit ideas will have you traveling in style without sacrificing an ounce of comfort.

The Classic Oversized Hoodie and Leggings Combo

Let’s start with the holy grail of airport outfits. An oversized hoodie paired with sleek leggings is basically the uniform of every smart traveler who’s figured out this whole flying thing. The hoodie keeps you warm when the airplane AC is doing the absolute most, and the leggings mean you can actually sit comfortably for more than five minutes.

Go for a neutral-colored hoodie in cream, gray, or black, and pair it with high-waisted black leggings. The trick here is making sure your leggings are the good kind—you know, the ones that don’t go see-through when you bend over. Add white sneakers and a crossbody bag, and you’ve got yourself a look that says “I fly so often, I could basically pilot this plane myself.” The best part? You can throw on a baseball cap and sunglasses if you’re not feeling the whole “morning person” vibe.

Oversized Blazer with Biker Shorts

Who says blazers are just for boardrooms? An oversized blazer thrown over biker shorts is that perfect mix of polished and casual that makes people think you’ve got your life together (even if you’re running on two hours of sleep and pure caffeine). This look is chef’s kiss for those shoulder-season travel days when you can’t figure out if you need a jacket or not.

Pick a blazer in a fun color like camel, sage green, or even a subtle plaid. The biker shorts keep things sporty and comfortable, while the blazer elevates the whole vibe. Finish with chunky sneakers or slides, and carry a structured tote bag. I love this outfit because you can literally peel off the blazer mid-flight if you get too warm, and you’re still looking cute underneath. Plus, the pockets in a blazer? Game changer for boarding passes and snacks.

Baggy Jeans and Crop Sweater Situation

Baggy jeans are having a major moment right now, and honestly, it’s about time. Wide-leg or straight-leg jeans paired with a cropped sweater create this relaxed silhouette that’s both trendy and travel-friendly. The crop keeps the proportions balanced so you don’t look like you’re drowning in fabric, while the loose jeans mean you can actually breathe and move freely.

Go for light-wash or vintage-style denim and pair it with a ribbed knit crop in a warm tone like rust, cream, or chocolate brown. Throw on some platform sneakers or loafers, and add a few gold hoops for that “I didn’t try too hard but I definitely did” energy. The beauty of this look is that it works for basically any destination—beach vacation, city break, or visiting family. Super versatile, super comfortable, and super cute.

Oversized Button-Down with Bike Shorts

There’s something so effortlessly cool about an oversized button-down shirt styled as a mini dress with bike shorts underneath. It’s giving relaxed weekend vibes while still looking put-together enough that people might think you’re someone important. Maybe an off-duty model? A cool influencer? Let them wonder.

Choose a crisp white or striped button-down and leave a few buttons undone for that casual feel. The bike shorts underneath mean you’re covered and comfortable, which is crucial when you’re climbing over people to get to your window seat. Add white sneakers, a mini backpack, and some dainty necklaces. Pro tip: roll up the sleeves for an extra touch of “I just threw this on and looked amazing.” This outfit photographs like a dream, so yes, take that airport mirror selfie.

Matching Sweatsuit in a Fun Color

Okay, matching sweatsuits had a whole renaissance and they’re not going anywhere. A coordinated hoodie and sweatpants set in something other than basic gray makes you look intentional and stylish, not like you just rolled out of bed (even if you totally did). The key is choosing the right color to make it feel elevated.

Think dusty pink, sage green, lavender, or even a rich brown. These colors feel fresh and put-together without trying too hard. Keep your sneakers clean and white, throw on some gold jewelry, and carry a sleek bag. The matching aspect makes it look like an actual outfit choice rather than just comfort clothes. Plus, you’ll be cozy for the entire journey, and isn’t that the whole point? This is peak “I’m comfortable but make it fashion” energy ✨.

Oversized Denim Jacket Over a Maxi Dress

For those transitional weather days when you need options, an oversized denim jacket layered over a flowy maxi dress is absolute perfection. The dress keeps you feeling feminine and breezy, while the denim jacket adds structure and warmth when the airport AC is absolutely brutal.

Go for a simple solid-colored maxi in black, olive, or tan, and choose a light-wash or medium-wash denim jacket that hits below your hips. Slip-on sneakers or flat sandals work perfectly here, depending on where you’re headed. Add a tote bag or crossbody, and you’re set. I love this combo because you can easily tie the jacket around your waist once you land somewhere warm, and the dress is comfortable enough to nap in on the plane. The layers give you options, which is always a win when traveling.

Wide-Leg Trousers with a Fitted Tank

If you want to look a little more elevated without sacrificing comfort, wide-leg trousers paired with a simple fitted tank is your answer. This look feels very “I have my life together and I travel first class” even if you’re definitely in economy with the rest of us.

Choose flowy trousers in linen or a soft knit fabric in neutral tones like beige, black, or navy. The fitted tank balances out the volume of the pants and shows that yes, you do have a figure under all that fabric. Layer with an oversized cardigan or denim jacket for warmth, and finish with loafers or minimal sneakers. Throw your hair in a slick bun, add some statement earrings, and suddenly you’re that chic airport person everyone lowkey wants to be. The trousers move with you, never feel restrictive, and look polished from takeoff to landing.

Oversized Cardigan as a Jacket

Here’s a little secret: a long, oversized cardigan can completely replace a jacket and give you that cozy-chic vibe that’s perfect for travel. Style it over a simple tee and your favorite comfortable jeans or leggings, and you’ve got instant warmth without the bulk of an actual coat.

Look for cardigans in chunky knits or soft cashmere blends in colors like oatmeal, camel, or charcoal. The length should hit mid-thigh or below for maximum impact. Pair with straight-leg jeans and ankle boots, or go casual with leggings and sneakers. Add a belt bag to keep your hands free, and you’re good to go. The cardigan is easy to take on and off during security and can double as a blanket on the plane. Some would say a scarf works better for warmth, but IMO the cardigan wins because it’s basically wearing a hug.

Graphic Oversized Tee with Joggers

Sometimes you just want to keep it super simple, and that’s where an oversized graphic tee paired with joggers comes in clutch. This look is perfect for early morning flights when you literally cannot be bothered with anything complicated. Zero effort, maximum comfort, still cute.

Pick a vintage-style band tee or a cool graphic that shows your personality, and pair it with tapered joggers in black, gray, or olive. The tapered style keeps things looking intentional rather than sloppy. Throw on your favorite sneakers, add a baseball cap and some hoops, and you’re done. Layer with a bomber jacket or zip-up hoodie if you need extra warmth. This outfit is basically permission to prioritize comfort while still looking like you know what’s up. It’s casual, it’s cool, and it’s perfect for long travel days.

Oversized Sweater Dress with Sneakers

If you’re team “one and done” when it comes to getting dressed, an oversized sweater dress is about to become your new best friend. It’s technically a dress, so you feel put-together, but it’s really just a very long, cozy sweater. Win-win.

Choose a ribbed knit or cable-knit sweater dress in a neutral shade, and style it with white or black chunky sneakers. You can add biker shorts or leggings underneath if you want extra coverage and warmth. Throw on some knee-high socks for a cute touch, or keep it simple with no-show socks. A small shoulder bag or backpack completes the look. The dress is comfortable enough to curl up and nap in, but you’ll still look stylish walking through the airport. Plus, when you arrive at your destination, just swap the sneakers for boots and you’ve got a whole new outfit vibe.

Longline Puffer Vest Over Loungewear

Puffer vests are having a serious moment, and the longline version paired with cozy loungewear is perfect for airport style. The vest adds that trendy, sporty element while keeping your arms free to wrestle with your carry-on or grab your coffee.

Style a longline puffer vest in black, olive, or tan over a matching sweatsuit or a simple tee and joggers combo. The vest provides warmth without making you feel like you’re overheating the second you step inside. Finish with clean sneakers and a baseball cap. I once tried doing a cropped puffer vest with this look and let’s just say it totally threw off the proportions. The longline version is where it’s at. This outfit is practical, comfortable, and has that athletic-chic vibe that somehow makes you look like you work out regularly (even if you definitely don’t).

Oversized Shacket with Jeans

The shacket—that magical shirt-jacket hybrid—is perfect for travel because it’s substantial enough to keep you warm but not as bulky as a real jacket. Style an oversized shacket with your comfiest jeans, and you’ve got an outfit that works from the airport to exploring your destination.

Go for a flannel or corduroy shacket in fall colors like burgundy, forest green, or classic plaid. Pair with straight-leg or mom jeans and a simple white tee or bodysuit underneath. Ankle boots or platform sneakers work great here. The shacket has this cool, outdoorsy vibe that makes you look like you’re about to go on some Instagram-worthy adventure. Plus, the pockets are clutch for storing all your random travel essentials. You can button it up for warmth or leave it open for a more relaxed look. Super versatile and endlessly stylish.

Oversized Hoodie Dress with Thigh-High Boots

For those who want to make a statement while staying comfortable, an oversized hoodie dress paired with thigh-high boots is bold, fun, and surprisingly practical for travel. Yes, I said thigh-high boots for the airport. Hear me out.

Choose a hoodie dress that hits mid-thigh in a solid color like black, gray, or camel. The flat or low-heeled thigh-high boots elongate your legs and add drama without being uncomfortable (skip the stiletto versions, obviously). This look is perfect if you’re heading somewhere you’ll want to look good immediately upon landing. Add a structured bag and some minimal jewelry, and you’ve created this cool, fashion-forward vibe that still allows you to be comfy on the plane. The boots mean you’re not dealing with extra shoes in your luggage, and the hoodie dress is basically socially acceptable pajamas. Is it even an airport outfit if you’re not maximizing both style and comfort?

Your New Travel Wardrobe Awaits

There you have it—13 oversized airport outfit ideas that prove you don’t have to choose between looking good and feeling comfortable. Whether you’re team matching sweatsuit or prefer the elevated vibe of wide-leg trousers and a blazer, there’s something here for every style and every destination. The key is choosing pieces that move with you, keep you comfortable during those long flights, and still make you feel like the stylish traveler you are.

So next time you’re packing for a trip, remember: oversized is the move. Your body will thank you, your Instagram followers will be impressed, and you’ll actually enjoy the journey instead of counting down the minutes until you can change clothes. Now go forth and travel in style, because life’s too short for uncomfortable airport outfits ✨.