Instagram/@varley
Picture this: LaGuardia security, 5:47 AM. I'm standing there barefoot like an idiot, boots in one hand, trying not to drop my phone with the other. My hair's doing... something. And yet I'm still desperately attempting to channel some kind of "I fly private" energy. This ridiculous contradiction—being simultaneously at your most vulnerable and trying to look sophisticated—pretty much sums up what airport style actually means.
Look, between the endless security lines and delayed connections (not to mention that special airplane air that sucks the life out of everything), airports are basically outfit boot camp. Think of this as your pre-flight briefing from someone who's figured out how to look halfway decent while being fully prepared to sleep on those questionable airport surfaces. Because here's the thing—real airport style? It's not about looking perfect. It's about being ready for literally anything.
The Fundamental Paradox
Airport rule #1: when uncertain, wear knit. Instagram/@ellandemm_co
So airport style lives in this impossible space between two totally opposite needs: wanting to curl up in the fetal position in seat 17B versus strutting through the terminal like you're shooting a perfume ad. It's basically Schrödinger's outfit—is it pajamas? Is it a power suit? Nobody knows until another traveler actually sees you.
The secret? Forget about it being one outfit. Start thinking of it more like... okay, you know those Japanese bento boxes where everything has its own little compartment? That's what you're going for. You're not just throwing on clothes. You're basically assembling a wearable survival kit that happens to look good.
1. The Foundation Formula
Cashmere pants and cashmere sweater—the perfect combo for an airport. Tuckernuck at tnuck.com
Your base layer is basically your flight suit—this is the stuff that decides whether you stumble off a red-eye looking vaguely human or completely haunted. Here's how I think about it:
The Holy Trinity:
- Soft knit top (cashmere blend if you're fancy, modal if you're practical)
- Something stretchy on the bottom that could maybe pass for "real pants" (ponte pants have saved my life more than once)
- Breathable undergarments (seriously, now is NOT the time for your complicated lingerie)
Here's my cardinal rule: no stretch? Then it doesn't fly with me. Rigid fabrics and long flights are basically mortal enemies. Trust me—anyone who's tried to do a transcontinental flight in regular denim learns this lesson real quick.
2. The Stretch Test
Stretchy ponte pants posing as "real" trousers? One of the best airport hacks. Quince at quince.com
Before you leave home, perform what I call the "Terminal Yoga Check":
- Can you reach overhead bins without exposing skin?
- Can you cross your legs in every conceivable position?
- Can you sprint to Gate Z99 without chafing?
If the answer to any of these is no, return to your closet immediately.
The Layering System: A Technical Manual
Ribbed henley—Favorite Daughter (saksfifthavenue.com), leather leggings—SPRWMN (bergdorfgoodman.com), tweed blazer—Brunello Cucinelli (saksfifthavenue.com), cut-out flats—Stuart Weitzman (saksfifthavenue.com), large suede bag—Prada (saksfifthavenue.com), cashmere scarf—N.Peal (farfetch.com), Napa leather gloves—Portolano (bergdorfgoodman.com), double knot earrings—Heaven Mayhem (farfetch.com)
Okay, think about layers the way you think about airline service classes. You've got economy, premium, and first—except you're wearing all of them at once.
Economy Layer (Base) This is your sleep outfit in disguise. Current favorite: a supremely soft gray henley that looks intentional but feels like stolen hotel bedding, paired with what I call "executive leggings"—thick enough to pass as pants, stretchy enough for in-flight contortions.
Premium Layer (The Transformer) This is where the magic happens. A structured blazer or leather jacket that instantly transforms your glorified pajamas into "I have a driver waiting" territory. The trick: it must work equally well draped over your shoulders or stuffed into overhead bins.
First Class Layer (The Statement) One spectacular accessory that does all the heavy lifting. Could be:
- An obscenely soft cashmere wrap (doubles as blanket)
- A structured bag that screams "I have my life together"
- Sunglasses that cost more than your flight (or at least look like that)
The Shoe Equation
Airport ally = comfortable, roomy, slip-ons. Skip the laces, skip the hassle. Instagram/@veja
Airport footwear follows a simple formula: Take how easy they are to remove, add the walking distance you'll cover, factor in actual comfort, then subtract however much style you're sacrificing = Your Perfect Airport Shoe
Here's what you absolutely need: genuinely comfortable shoes (and I mean actually comfortable, with decent width—narrow shoes and airports are a terrible combo). Pro tip? Go up half a size. Trust me, your feet will thank you at baggage claim when they inevitably do that weird airplane swelling thing.
The Contenders:
Knit loafers that flex with you—ideal in the air. Instagram/@vivaia_official
The Slip-On Sneaker Renaissance
Veja, Gola, or those Bottega Veneta dupes everyone pretends aren't dupes. They whisper "I exercise recreationally" while actually meaning "I refuse to tie laces at 6 AM."
The Elevated Flat
Leather loafers or ballet flats that have transcended their prep school origins. Bonus points if they have a slight platform—every inch counts when you're reaching for overhead bins.
The Chelsea Boot Compromise For those who refuse to abandon structure entirely. Look for elastic panels generous enough to accommodate in-flight swelling.
The Sock Strategy
This is where amateurs reveal themselves. Compression socks that look like regular socks are your secret weapon. Your ankles will thank you, and no one needs to know you're essentially wearing medical equipment.
The Accessories Audit
Messenger/weekender/backpack—all wins. Pack a clear pouch for TSA-friendly minis. Instagram/@maisondesabre
The Carry Hierarchy
Your bag system should work like Russian dolls:
- The Statement Tote: Large enough for a laptop, structured enough to photograph well, soft enough to squeeze under seats
- The Security Pouch: A small crossbody or belt bag for documents (wearing your passport is the ultimate power move)
- The Emergency Kit: Clear bag with skincare that makes you look like a Glossier ad, not a TSA suspect
The Textile Technology
Think kilt energy: one piece, many jobs. Large scarves do it all at the airport. Acne Studios at acnestudios.com
The Scarf Sciences A large scarf is non-negotiable:
- Blanket on plane
- Pillow when folded
- Style statement when draped
- Privacy screen from chatty seatmates
Oversized cashmere wraps somehow make you feel rich even when you're eating a sad airport sandwich at 6 AM.
The Jewelry Dilemma Nothing that beeps, nothing you can't sleep in, nothing that screams "rob me" in foreign capitals. My formula: one statement watch, simple hoops, maybe a delicate necklace. Stack rings stay home or relocate to hand luggage—nothing worse than sausage fingers at altitude.
The Grooming Gospel
Flights are stressful—don't board unprepared. Slip moisturizers into your carry-on; future you will cheer. Instagram/@glowrecipe
Pre-Flight Prep
- Hair in a style that survives horizontal positions (low bun, slicked back, or embracing natural texture)
- Minimal makeup that won't transfer onto tray tables
- Skincare that treats the plane like the dehydration chamber it is
The In-Flight Refresh Your bathroom kit may include:
- Face mist (because moisture)
- Lip balm (industrial strength)
- Hand cream (airplane air is basically the Sahara)
- Dry shampoo (for those emergency hair situations)
- Some kind of subtle fragrance (emphasis on subtle—your seatmates will thank you)
The Psychology of Airport Presence
Brands don't make style. Confidence and attitude do. Reiss at reiss.com
Here's what nobody tells you: airport style is like, what, 30% clothes? The rest is just... how you move through space. I watched this woman at JFK once—head-to-toe designer everything—but she was sprint-walking with this panicked expression and dragging her Goyard like it personally offended her. Meanwhile, the girl in Target leggings next to her? Gliding through TSA PreCheck like she owned the place.
The secret sauce:
- Walk with purpose, even when lost
- Master the art of elegant queueing
- Perfect your "I'm not bothered" face for delays
- Treat security like a meditation exercise
The Situational Wardrobe
Step one: comfortable pants. Everything else follows. Marks and Spencer at marksandspencer.com
The Business Trip Uniform Start with black ponte pants and a white silk shell. Throw on that structured blazer, grab your leather tote. Need to look more pulled-together at arrivals? Red lipstick. Done. Maybe add some geometric earrings if you're feeling fancy.
The Vacation Departure Linen pants (the wrinkles are inevitable, embrace them), soft cotton tee, denim jacket for the aggressive AC. A hat if you can manage it without looking like you're cosplaying. Silk scarf and big sunglasses transform the whole thing from "college backpacker" to "might own a vineyard."
The Red-Eye Survival Kit Base: Matching knit set (yes, really) Elevation: Cashmere wrap + leather slides Emergency human: Face mist + coffee
The Reality Check
It's fine if your airport outfit is loungewear. Sometimes it's better, actually. Leset pointelle pants and t-shirt at modaoperandi.com
Can we be real for a second? Sometimes you're gonna find yourself in the airport Starbucks at 5 AM, running on yesterday's deodorant and tomorrow's anxiety. That's fine. Actually, it's more than fine. It's normal.
Your Pre-Flight Checklist
Before every trip, ask yourself:
- [ ] Can I sleep in this?
- [ ] Can I run in this?
- [ ] Can I sit for 8 hours without wanting to die?
- [ ] Do I have layers for temperature chaos?
- [ ] Have I packed something—anything—that makes me feel like a boss?
- [ ] Could I theoretically go straight from the plane to a meeting/beach/bed without a total outfit overhaul?
The Final Approach
Best travel tip: be realistic. Comfort over insta-aesthetics. Zara at zara.com
Look, I'm not gonna pretend airport style is about emerging from a 14-hour flight looking like a supermodel. That's insane. It's really just about creating a system that doesn't completely fail you when you need it most. Can it handle security? Can it survive the middle seat? Will you hate yourself by hour six? These are the real questions.
The thing is, when you're stumbling around your bedroom at 4 AM trying to get dressed for that dawn flight, you're not picking an outfit. You're assembling armor. Soft armor, sure. Made of modal and cashmere and whatever miracle fabric doesn't wrinkle. But armor nonetheless.
So next time you see someone gliding through the terminal looking mysteriously put-together at an ungodly hour? That might be me, armed with compression socks and industrial-strength concealer, proving that sometimes the best travel hack is just accepting that perfect is the enemy of comfortable—and comfortable is the secret to actually looking good.
The Quick Reference Card
Perfection won't survive a transatlantic—comfort with cool will. Lululemon at shop.lululemon.com
Always Pack:
- Cashmere wrap (blanket/scarf/pillow)
- Slip-on shoes with grip
- Empty water bottle (hydration is chic)
- Travel-size everything
- Phone charger that reaches airplane outlets
- The confidence to eat airport food in designer clothes
Never Pack:
- Complicated shoes
- Dry-clean-only anything
- Underwire that sets off metal detectors
- Perfume that announces your arrival three rows away
- The delusion that you'll look perfect after international flights
Remember: The best airport outfit is the one that gets you from point A to point B without sacrificing your sanity or your style. Everything else is just details.
