15 Preppy Airport Outfit Ideas for Classic Travel Style

Let’s be real: airport outfits are their own category of dressing. You need to look put-together enough that you don’t feel like a total mess in your travel selfies, but comfortable enough that you’re not adjusting your waistband every five seconds. And if you’re anything like me, you want that effortless preppy vibe that says “I definitely have my life together” even when you’re running on three hours of sleep and airport coffee.

Here’s the thing about preppy airport style: it’s basically foolproof. We’re talking classic pieces, elevated basics, and that polished-but-not-trying-too-hard energy that just works. Whether you’re catching a 6 AM flight or jet-setting somewhere fabulous, these outfit ideas will have you looking like you belong in a J.Crew catalog (in the best way possible). So grab your carry-on and let’s talk about the preppy airport outfit ideas that’ll make TSA your personal runway.

The Cable Knit Sweater and Leggings Combo

This is the outfit I reach for when I want to feel like I’m wearing pajamas but still look socially acceptable. A chunky cable knit sweater in cream or navy paired with black leggings is basically the uniform of chic travelers everywhere. The sweater gives you that cozy, classic prep school vibe while the leggings keep things comfortable for those long security lines.

Style this with white sneakers (because blisters are not the vibe) and a structured tote bag. Throw your hair in a sleek low ponytail and add some gold hoops. The beauty of this look? You can layer a trench coat over it if you’re feeling extra, or just rock the sweater solo. Either way, you’ll look like you know exactly what you’re doing, even if you’re internally panicking about whether you remembered your charger.

Polo Shirt Tucked Into High-Waisted Trousers

Okay, hear me out on this one. I know what you’re thinking: “A polo? At the airport?” But trust me, a fitted polo shirt tucked into high-waisted trousers is giving understated elegance. Go for a classic white or navy polo and pair it with tailored trousers in a neutral shade. This combo screams “I’m professional but also fun” which is exactly the energy you want when traveling.

The high-waisted cut keeps everything comfortable around your waist (no tight waistbands digging in mid-flight), and the polo adds just enough structure to look intentional. Add loafers or ballet flats, and you’ve got yourself a look that transitions perfectly from airport to arrival destination. Pop on some oversized sunglasses and suddenly you’re that person everyone wants to be.

Cashmere Hoodie with Straight Leg Jeans

Is it even a preppy airport outfit without cashmere? This look takes the casual hoodie and elevates it with luxe fabric. A cashmere hoodie in a neutral tone (think camel, grey, or navy) paired with straight leg jeans is the perfect balance of comfort and polish. The cashmere keeps you cozy during those freezing plane rides while still looking incredibly chic.

Roll up the sleeves slightly and add white leather sneakers for that effortlessly cool vibe. Throw a crossbody bag across your chest so your hands are free for coffee and boarding passes. The straight leg jeans are key here because they’re not too tight, not too loose, and they look intentional. Plus, they won’t wrinkle as much as other styles, which is crucial when you’re sitting for hours.

Blazer Over a White Tee and Joggers

Want to look like you mean business but still be able to nap comfortably? This is your outfit. A structured blazer (navy or black works perfectly) thrown over a crisp white tee and matching joggers creates this interesting contrast between polished and relaxed. The blazer instantly elevates what could otherwise look too casual, while the joggers keep you from wanting to change the second you sit down.

Go for sleek joggers in a neutral color, not the super baggy kind. Add white or tan sneakers and minimal gold jewelry. The trick here is keeping everything fitted and intentional so you look put-together rather than like you just rolled out of bed. Bonus points if your blazer has pockets because where else are you supposed to put your lip balm?

Striped Button Down with Chinos

Nothing says preppy quite like stripes. A classic striped button-down (blue and white is iconic) paired with well-fitted chinos is the ultimate airport power move. This look is giving “I summer in the Hamptons” energy, and honestly, who doesn’t want that?

Keep the chinos in a neutral shade like khaki, navy, or white, and roll them at the ankle for a more casual vibe. Slip-on sneakers or loafers complete the look without adding any hassle at security. The button-down can be worn fully buttoned for a more polished feel or with the top few buttons undone for something more relaxed. Either way, you’ll look like you have impeccable taste and probably own a boat.

Crewneck Sweatshirt and Pleated Midi Skirt

This combination is so unexpectedly chic that people will think you planned your outfit for weeks. A classic crewneck sweatshirt (bonus points if it’s from a university or has a vintage vibe) paired with a pleated midi skirt creates this fun mix of sporty and feminine. The sweatshirt keeps you comfortable while the skirt adds that preppy, polished element.

Choose a skirt in a neutral color or even a fun plaid pattern if you’re feeling bold. White sneakers keep it casual, or you can do low-heeled mules if you want to feel a bit more dressed up. Add a canvas tote bag and you’ve got a look that’s Instagram-worthy without trying too hard. The midi length is perfect for travel because it’s not too short (hello, awkward airplane seats) but still shows off your shoes.

Quarter Zip Pullover with Bike Shorts

I once judged people who wore bike shorts to the airport, and then I tried it. Game changer. A preppy quarter-zip pullover (think Patagonia or a classic rugby style) paired with high-waisted bike shorts is comfortable AF while still looking intentional. The quarter-zip adds that sporty-preppy element that’s having a major moment right now.

Go for black bike shorts to keep things versatile and add white crew socks with sneakers for that athletic aesthetic. The key is making sure your bike shorts are the right length (mid-thigh is ideal) and not too tight. Layer a baseball cap and some gold jewelry to balance the sporty vibe with something a bit more refined. This outfit is basically saying “I work out but also have taste” and I’m here for it.

Cardigan Set with Wide Leg Pants

Matching cardigan sets are having their moment, and airports are the perfect place to show them off. A coordinated cardigan and tank set in a neutral color paired with wide leg pants creates this elevated, cohesive look that requires minimal effort. The matching set does all the work for you, and the wide leg pants add movement and sophistication.

Choose pants in a complementary neutral shade and add loafers or mules. The beauty of this outfit is that you can remove the cardigan if you get warm and still look completely put-together in just the tank and pants. Add a structured handbag and some simple jewelry, and you’ve basically cracked the code on airport chic. Plus, everything’s stretchy and comfortable, which is non-negotiable for travel.

Oxford Shirt Dress with Sneakers

Sometimes the easiest outfit is just one piece, and a classic oxford shirt dress delivers every time. This preppy staple works perfectly for airports because it’s literally one item you have to think about. Go for a white or light blue shirt dress and cinch it at the waist with a belt for definition.

White leather sneakers keep the look casual and travel-friendly, while a crossbody bag keeps your hands free. You can wear the dress fully buttoned with the collar up for a more traditional preppy vibe, or leave a few buttons undone and roll the sleeves for something more relaxed. Add a watch and simple studs, and you’re golden. The shirt dress is also super versatile for wherever you’re headed, which means less packing. Smart and stylish? Yes, please.

Turtleneck Under a Vest with Jeans

Layering is the secret weapon of preppy style, and this combo proves it. A fitted turtleneck (black, cream, or navy) layered under a puffer vest or quilted vest paired with straight leg jeans is peak preppy airport aesthetic. The turtleneck keeps you warm without bulk, while the vest adds dimension and that outdoorsy-chic vibe.

Choose a vest in a neutral color or even a fun pattern like plaid or Fair Isle. Add Chelsea boots or sleek sneakers and a leather tote bag. This outfit works because each layer serves a purpose: the turtleneck is your base layer for the plane, the vest adds warmth in the terminal, and you can easily remove the vest if needed. It’s strategic dressing at its finest, and you’ll look incredibly put-together doing it.

Collared Knit Polo Dress

A knit polo dress is like the sophisticated cousin of your favorite t-shirt dress. This one-piece wonder combines the structure of a polo with the ease of a dress, creating the perfect airport outfit that requires zero coordination. Go for a neutral color like navy, forest green, or camel for maximum versatility.

The collar adds that preppy detail that elevates the whole look, while the knit fabric keeps you comfortable for hours. Pair with white sneakers and a canvas tote for a more casual vibe, or dress it up with loafers and a structured handbag. Add a baseball cap if you’re having a bad hair day (we’ve all been there), and you’re set. This dress is basically the uniform of people who travel often and have figured out the formula.

Henley Top with Paper Bag Waist Pants

Henley tops are criminally underrated in the preppy wardrobe. A long-sleeve henley in a neutral color paired with paper bag waist pants creates this effortlessly chic look that’s comfortable enough for travel but polished enough to look intentional. The henley has that casual-cool vibe while the paper bag waist adds structure and style.

Choose pants in a complementary neutral and add loafers or mules. The elastic waistband hidden under that cute tie detail means you can breathe and eat airport snacks without restriction (crucial). Roll the henley sleeves to three-quarter length for a more relaxed feel, and add a crossbody bag plus some minimal jewelry. This outfit hits that sweet spot between trying and not trying at all.

Crewneck and Trousers with Loafers

Sometimes the simplest combinations are the chicest. A classic crewneck sweater in a solid color paired with tailored trousers and leather loafers is preppy perfection. This outfit looks like you put thought into your look without being too dressy for travel. The crewneck keeps you cozy while the trousers add polish.

Go for a neutral color palette to keep everything cohesive and add a structured tote or weekender bag. The loafers are key here because they’re easy to slip on and off at security (those velcro sneakers who?) while still looking incredibly polished. Tuck in the sweater slightly in the front for a more modern silhouette, and add a watch or simple bracelet. This is the outfit that makes people think you have your life together, even if you definitely don’t.

Rugby Shirt with Denim Shorts

For warmer destinations or those weird transitional weather days, a classic rugby shirt paired with denim shorts is the move. The rugby shirt gives major preppy-sporty vibes with its stripes and collar, while the denim shorts keep things casual and comfortable. Go for a fitted rugby style rather than oversized to keep the proportions balanced.

Choose denim shorts that hit mid-thigh (nothing too short for airplane seats) and add white sneakers or canvas slip-ons. A baseball cap and sunglasses complete the look, giving you that “I’m headed somewhere fun” energy. The rugby shirt also works as a layering piece if you get cold, so it’s functional and stylish. Plus, the collar means you still look put-together even in shorts, which is the whole point of preppy style.

Knit Polo and Midi Skirt

There’s something about a knit polo that just screams elevated basics. Pairing one with a midi skirt creates this feminine yet structured look that’s perfect for airports. Go for a fitted knit polo in a solid color and match it with a pleated or A-line midi skirt in a complementary shade. The knit keeps you comfortable while the midi skirt adds sophistication.

Tuck the polo in completely to define your waist and add either sneakers for casual or loafers for slightly more dressed up. A structured handbag and simple jewelry complete the look. This outfit works because it’s comfortable enough for travel but polished enough that you could go straight to dinner from the airport. Strategic dressing at its finest, and you’ll look amazing in your travel photos.

Your Preppy Airport Style Sorted

There you have it: 17 preppy airport outfit ideas that prove you don’t have to sacrifice style for comfort when traveling. The beauty of preppy style is that it’s built on classic pieces that work together effortlessly, which is exactly what you need when you’re trying to look cute at 5 AM. Whether you’re reaching for a cable knit sweater, a striped button-down, or a matching cardigan set, these looks have got you covered.

The key to nailing airport style is choosing pieces that make you feel confident and comfortable while still looking intentional. So next time you’re packing for a trip, skip the ratty sweatpants and reach for one of these preppy combinations instead. Your future self (and your Instagram feed) will thank you ✨