From Airport to Evening: Outfits that Evolve

Jessie Beck

The quest for the perfect airplane outfit: if you’re here, you’re probably on it, searching for an ensemble that’s comfortable yet stylish; easy yet put together; sweatpant-like, but not sweatpants. While all of these qualities are important for airplane outfits, we often forget about what happens once you get off the plane. This airplane outfit, will it also work for your post-flight activities?

In my years of traveling, seldom do my time-optimized, jam-packed itineraries allow for a wardrobe change between landing in my destination and the next activity. Often, I’m running straight from the airport to a conference, dinner with friends, or a mini-road trip to my real destination several hours away. In these situations, I need clothes that evolve as my day unfurls.

Which is why, with the help of fellow Tortuga writer Shawn Forno, we have compiled a list of airplane outfit ideas for men and women that can sustain as many scene changes as you can throw at them. If you need ideas for airplane outfits you can take from flight to night out, scroll onwards, fearless adventurer:

Perfect Airplane to Destination Outfits

We know not every trip is the same, so below are five different outfit ideas for five different types of travel.

Climate Hopper Ladies: From Cold to Warm Weather

Fleeing winter for a little warm-weather escape? Then layers will be your best friend when choosing an outfit that works for both climates.

For a fashion forward and practical look, grab a mini or midi dress and layer it over a pair of jeggings. Worn under a long-line cardigan and a pair of lightweight sneakers, this combo will keep you warm on your way to the airport and in flight.

Styling Tip

Once you’re at your destination, add a pair of sunglasses and shed a layer (or three) before diving into your warm-weather adventures — sans pit stains (okay, I can’t make any promises on that, but you get the picture.)

If you’re traveling during the summer, this outfit works well for warm-to-warm weather travels too. Instead of wearing your jeggings and cardigan to the airport, put them in your carry on to combat the in-flight AC, and swap the sneakers for sandals.

Zara Crossed Dress – $36

First, grab a mini or midi dress. Choose one for your closet or consult my favorite, affordable brand for dresses: Zara.

Sunglasses, ASOS – $19

Hit the ground prepared with a pair of sunglasses. Find the intersection of stylish and affordable with ASOS.

Oak + Fort Sweater – $90

Worn under a long-line cardigan, this dress-legging-sweater trio will keep you warm on your way to the airport and in flight. I’m partial to Oak + Fort’s cardigans, since they’re nice quality but won’t break the bank.

Uniqlo Leggings Pants – $30

For a fashion forward and practical look, layer it over a pair of jeggings. Uniqlo is always a reliable source for affordable jeggings that look equally good under a dress or as pants with a top.

Soludos Linen Sneakers – $80

For a casual and comfy look, add a pair of fashion sneakers. Choose your favorite brand (TOMS and Adidas are always reliable) or try a pair from adventure-ready brand, Soludos.

Climate Hopper Men: From Cold to Warm Weather

You’re headed somewhere tropical, and can already feel those warm balmy evenings and hot summer nights calling you. The only problem is you’re coming from -20° weather on the way to the airport. Or maybe you’re just scared about being trapped on an icebox of a plane for the next 4.5 hours. No sweat (literally). You just need the right gear:

Buff Scarf – $30

Stylish as heck, useful as hell. Wrap this bad boy around your neck on the flight to stave off a chill, or use it as an eye mask to catch some zzzs on the flight. Then, trek the city when you land and wet it at the nearest fountain to cool you down. If you’re not into that Indiana Jones vibe, take it off and wad it into your back pocket.

Toms Classic Shoes – $50

I was late to the TOMs shoe party, but now I’m here. Slip on shoes are key to a comfy airport and airplane experience, and they transition to summer in the city with ease.

Airplane Socks – $18

Up your airplane game with a dedicated pair of comfy socks. You have your bag with you, so why not—and you’re ready to hit the tarmac like a boss.

Uniqlo Stretch Colored Jeans – $30

I’ve been rocking some version of these stretchy, fashionable jeans for nearly a decade now, and they haven’t let me down yet. Perfect for the plane, yet built for the city. They’re durable enough for hiking, stretchy enough for biking or climbing (or dancing), yet stylish enough for the club. Get a bright color so you can hit the ground running in your tropical paradise. I roll mine up when it gets warm or I feel like running around on the beach.

Bonus: If it’s really hot, you can just cut these into shorts. They’re not expensive, and now you have dope shorts.

Slim Cotton Popover Shirt – $59

A merino t-shirt is a great choice for practically any occasion. No, really. They rule. But if you’re looking to up your game juuuuust a little bit, consider the popover shirt. These are the button up shirts that don’t actually button all the way down. Kind of like a henley, but way more comfy and stylish like Gosling. Popover shirts travel well, look great, and you wear them alone on hot days or over several layers if it’s chilly.

The Sleeper: Ladies Outfits for Long-Hauls and Red-Eyes

Whether it’s a trans-Pacific flight to Asia or a red-eye from LA to New York, some flights are made for snoozing. Those same flights, however, often land at early (7 or 9a.m.), hit-the-ground running hours when you might find yourself unable to check in and take a nap for several hours, or unwilling to waste a day in this new place sleeping. You need an outfit that’s ready to roll.

For this, grab your favorite t-shirt or tank, a slouchy sweater you can curl up in, fashion leggings, and slip ons. Pack a blanket scarf and socks for extra in-flight coziness. Once you land, simply do a quick freshen-up in the bathroom.

The beauty of traveling carry on only means you’ll have your entire capsule wardrobe within reach as you sit around waiting to land.

Styling Tip

To really transform your look (and help yourself feel like you’re not walking around in your PJs) swap your sweater for an easy to pack bomber jacket and your sneakers for flats. Make our suggestions your own — and own it.

Whatever combo you choose, simply do a quick freshen-up in the bathroom once you land, so you can jump straight from plane to (travel) plan.

ADAY Leggings – $135

To start, reach for a pair of comfortable fashion leggings like the Throw and Roll leggings from ADAY. Unlike workout leggings, they look more fashionable and are near-impossible to wrinkle — even after a 6-hour airplane nap.

The LOFT Sweater – $60

Next, layer on a slouchy sweater you can curl up in. For something cozy, easy to match, and stylish, The LOFT and their sister brand, Lou + Grey, always have something in their current line (regardless of season).

Lululemon Vinyasa Scarf – $48

For extra in-flight coziness, pack a pair of socks and a blanket scarf, like Lululemon’s Vinyasa Scarf. It’s soft, comes in eight different colors, and the snaps on either end transform it into an infinity scarf that won’t fall off while you snooze.

Gap T-shirt or Tank – $18

For your top, grab your favorite (breathable) t-shirt or tank. If you don’t already have one, take a look at Gap or Everlane. Both make affordable, basic tanks and t-shirts perfect for layering.

Sperry’s Slip On Shoes – $75

Finish your outfit with a pair of sneakers you can easily slip on and off during the flight, but comfortable enough to walk around in once you arrive. For this, we always love a good pair of TOMS or Sperry’s — which makes sneakers in addition to its classic boat shoes.

The Sleeper: Men’s Outfits for Long-Hauls and Red-Eyes

They say footie pajamas aren’t hip, but you don’t care about hip. You care about waking up, looking fresh, and actually having the energy to enjoy your destination right away. To that end:

Happy Socks – $18

I mentioned these for going from cold to warm weather, but a dedicated pair of socks for air travel is just a good idea—especially if you’re planning to get some sleep. You don’t want to sleep with your shoes on, and you’re not a monster. Don’t gross everyone out with stinky toes. Wear a fresh pair of cozy socks and sleep like a jetsetting baby.

Lewis & Clark Comfort Eye Mask – $12

A quality padded eye mask will quickly become your most valued possession. The little pocket is perfect for stashing a sleeping aid, or ear plugs when your bluetooth headphones die somewhere over the Pacific ocean. Don’t leave home without it.

BetaBrand No Sweat Travel Hoodie – $78

Don’t rely on that skuzzy airplane blanket to keep you warm on the flight. Bring your own lightweight hoodie, and get to sleep in style. The half zip design travels well, and looks great. Plus, the seamless design is comfy against the back a seat all night.

Manduka “Intentional” Pants – $92

Ignore the hippie name and embrace the sweet comfort of terry cloth pants that actually look awesome. I love these pants. The comfy drawstring waist, and flowy design looks great, and travels even better. If you’re dying to hit the ground running, you can even layer these pants over a pair of shorts and explode out of ’em like an NBA star running out of the locker room when you land. Honestly though, I think they look awesome as is.

Outlier Ultrafine Merino T-Shirt – $110

I can’t recommend this merino shirt enough. I wore it nearly everyday on my 6-week hike across Spain, and I wear it to the office in Midtown now. It’s stylish, so well made it’s ridiculous, and performs like a beast. Ultrafine merino is magic fabric. Get some if you can afford it. You won’t regret it. I can bike, climb, and ride the rush hour train in this thing without a whiff of sweat. Love. It.

Work (it) on the Road for Women: Outfits for Business Trips

If you travel for business, you may know this scenario well: hop on the earliest flight out, land at 8 a.m., and head straight to your first client meeting — luggage in tow. With a go-go-go schedule like this, you have to be ready to step off the plane and get straight to business with work clothes that are both comfortable and travel-ready.

To prep yourself to go from airplane to boardroom, start with a technical trouser and silk-poly blend blouse, which will be less likely to wrinkle the minute you sit down on the plane. Then, add a nice sweater or blazer to put it all together.

Styling Tip

For shoes, opt for a professional-looking loafer that you can last all day in. If you must wear heels, spare your feet. Wear flats in the airport and plane, then do a shoe swap en route from the airport.

ADAY Trousers – $125

To prep yourself to go from airplane to boardroom, start with a technical trouser, like ADAY’s Turn it Up pants. Professional in style but made of a nylon-elastane fabric that’s breathable, wrinkle-resistant, and travel ready, they hold up from 6 a.m. boarding call to 8 p.m. drinks with the boss.

Rothy’s Loafers – $165

For shoes, opt for a professional-looking loafer that you can last all day in, like the eco-friendly Rothy’s, which are said to be “as comfortable as sneakers”.

Amano Studio Accessories – $34

To polish off your outfit, add a necklace or pair of earrings. For both professional and everyday wear, I love everything by Amano Studio. Their jewelry adds a minimalist pop to outfit that’s just as appropriate for work as it is for play.

Everlane Blouse – $68

Pair your trouser with a silk-poly blend blouse, which will be less likely to wrinkle the minute you sit down on the plane. Everlane’s Japanese Weave blouse, made from a wrinkle-resistant triacetate fabric, is an ideal option.

Everlane Blazer – $135

Then, add a nice cardigan or blazer to put it all together. I typically opt for an Oak + Fort cardigan since my line of work is more business casual, but for a more buttoned up business look, try Everlane’s classic blazer, made from wool. Ministry of Supply also has a blazer well-reviewed by the business travel community — though at a higher price tag ($245).

Work (it) on the Road for Men: Outfits for Business Trips

Bluffworks Tailor Fit Travel Chinos – $125

I’ve said it before and I stand by it—the Bluffworks tailor fit chinos are the best travel pants I’ve ever worn. They repel sweat and stains, don’t get wrinkly, take an absolute ass kicking, and look and feel like the high quality, top of the line travel pants they are. You get what you pay for, and the more I wear these travel pants I can’t help thinking what a bargain they are at $125. You’ll wear these pants on every business trip for years to come. And they’ll still look brand new.

Uniqlo Airism Polo Shirt – $19

I don’t even understand this shirt. It feels like a sweat wicking gym shirt, but it’s cut and styled to look professional and classic. Right down to the starched collar. I wear this to dance events with my girlfriend, and I look dapper as hell. It soaks up sweat like a sponge.

People Footwear Stanley Shoes – $60

These lightweight, comfy, 3D printed mesh travel shoes don’t just look incredible, they feel like you’re wearing the future. And the future is light. I get compliments on these shoes every time I wear them, including business meetings. They’re great in all kinds of weather, travel great, and won’t add much weight to your bag if you decide to toss on a pair of sandals after the meeting is over. Honestly, you don’t need to bring another pair of shoes if you wear these perfect travel shoes.

Jetsetter Short Sleeve Dress Shirt – $98

The long sleeve business shirt look is so 2009. Ditch the stiff corporate look and embrace your digital nomad badass self with this stylish yet professional short sleeve dress shirt. 95% cotton for that soft feel, but 5% spandex for enough stretch to travel without wrinkling, even on the flight. Make a great first impression right off the plane with this hip, modern twist on a classic. If you really need sleeves, try the Daily Grind Wrinkle Free Dress Shirt ($98). They look good.

Bluffworks Gramercy Travel Blazer – $295

All the travel features you could ask for in a silhouette that says “closer.” 10 smart pockets. Zipper pockets. Passport pocket. Stretchable fabric. Machine washable. Say hello to your new pseudo carry on bag. This is my go-to travel blazer.

Women’s Weekender: Outfits for Quick Weekend Getaways

For some of us, wanderlust is often a weekend thing. Whether it’s a trip to wine country with your boo or a few days in New Orleans with your college besties, weekend travels start the minute you land. You need an outfit that can keep up.

Styling Tip

If you’re in for a casual evening, maybe give your cami a “French Tuck” (thanks Tan) but otherwise keep the outfit as is. To dress it up, swap the jean jacket for a sweater, add a couple of small accessories, and put on your best lipstick for a transformation.


Everlane Jeans – $68

To create a versatile outfit you can wear from airplane to dinner out, start first with a pair of neutral trousers or black jeans. Look for something with a little lycra or made from synthetic fibers, for wrinkle-free comfort while in-flight. Again, Everlane to the rescue.

TopShop Jacket – $90

Pull it together with your favorite jean jacket. A more oversized cut, like this one by TopShop, will give you a ready-to-hang look, but won’t be tight and uncomfortable in-flight the way a more fitted jacket might be.

Petites Jupes de Prune Top – $50

Pair it with a blouse, like this simple cami from French brand, Petites Jupes de Prune, that’s easy to layer but looks lovely on its own.

TOMS Mules – $90

Mules: they’re like the on-trend version of the slip-on sneaker. And yes, of course, TOMS makes a comfortable pair. Finish your outfit with these to give your outfit a versatile, fashion forward look you can last all day in. For additional options, check out travel ready brand, Soludos.

Men’s Weekender: Outfits for Quick Weekend Getaways

These are my favorite trips to take, and the easiest to pack for because they’re all about comfort and fun. You know you’re up against the clock, and you have nobody to impress.

Bonobos Riviera Short Sleeve Shirt – $88

I can’t get enough of this shirt. It feels tailor fitted, yet relaxed enough for lounging around. I prefer a sharp fit, and the Bonobos short sleeve shirts deliver. Bring this one shirt for that special occasion—even if it’s just Saturday night—and you’ll be the best dressed guy in the room. And you didn’t even have to check a bag.

RVCA Weekender Stretch Shorts – $39

It’s right there in the name. RVCA is a surf-centric brand built on function and style. And these shorts nailed it. If you’re looking to hit the waves after you leave your gate, snag a bright pair of these shorts and countdown the minutes til you land. The 2% elastane blend makes them comfy and great for travel

Scarpa Crux Approach Shoes – $89

If you’re just getting right into it from the airport, I can’t recommend a better travel shoe than the Scarpa Crux Approach Shoes. They are designed for hikers who rock climb, and they’re as close to perfect as I can imagine. They’re sturdy (I wore them every day on my 500+ mile hike across Spain), stylish (I wear them when I bike around NYC), and comfy. I didn’t get a single blister on my hike. They hold their shape pretty well thanks to the sturdy construction, so make sure you get a good fit out of the gate, because they won’t “break in” the way other (crappy) hiking shoes do.

Uniqlo AIRism Mesh Tank Top – $10

Don’t let the word “mesh” fool you. This is the best tank top in the world. It weighs next to nothing, fits great, keeps me cool, and works for any situation that requires a tank top… which is not often, but hey. Tanks tops make great layers. Truly the easiest thing to pack, this tank top is comfy, stylish, and designed to travel well. Pick up a few. You’ll like ’em.

The Bundle Up: Women’s Outfits for Winter Travel

Not sure what to wear for cold weather flights? Like the climate hop, layers are key — but you’ll also want to make sure you have a space in your bag to stash your (ideally) easy-to-pack-down jacket and scarf while running around the airport.

Start with a comfy t-shirt and your most comfortable jeans. For your warm outer layers, add a lightweight sweater and a down jacket. Toss on a pair of low-heeled or flat ankle boots and a scarf, and voila: a stylish cold-weather travel outfit you can wear both on the plane and off.

Gap T-Shirt – $18

Start with layer number one: your trusty, comfy t-shirt. Gap is always reliable for basic tees. However, if you’re willing to make the investment, opt for a Merino wool t-shirt instead. They’ll add warmth to your winter layers without leaving you a puddle of sweat underneath.

Oak + Fort Light Sweater – $48

For layer number two: add a lightweight pullover sweater that’ll pack down well when not in use. Again, Oak + Fort has simple, fashionable, and affordable sweaters that fit the bill.

Zara Scarf – $36

Finish it all off with a large, blanket scarf, like this one from Zara. And voila: you have a stylish cold-weather travel outfit you can wear both on the plane and off.

Just Black Jeans – $50

Grab your most comfortable jeans or jeggings — ideally a pair with a little elastic for optimal comfort. My go-to is Just Black Denim, though they’re hard to find outside California. Otherwise, Uniqlo’s jeggings will do the trick.

Sam Edelman Boots – $100

A pair of low-heeled or flat ankle boots are easy to slip on and off, but warm enough with a pair of serious socks to keep your feet warm in your cold-weather travels. Sam Edelman makes a pair that’s timeless, comfortable, and matches just about everything.

Patagonia Down Jacket – $200

For your final top layer: grab a down jacket, arguably the best winter jacket for travel. Patagonia makes wonderful high quality, warm, and easy to pack-down jackets. Plus, with their passion for the outdoors and taking care of their employees, they’re the just kind of company you want to support.

The Bundle Up: Men’s Outfits for Winter Travel

It’s tough to travel light when the weather is so dang cold, but you can still look good, stay warm, and pack like a pro in winter.

Bonobos Shirt Jacket – $128

Great for layering under heavy coats, but still warm enough all on its own, the shirt/jacket or “shaket” is a winter travel staple. Use it to stay warm on the plane without the bulk, and hit the winter weather like a winner with pockets for your stuff, and style for days.

Buff Midweight Merino Scarf – $32

All the best parts of a scarf without the bulk. Invest in merino and reap the rewards of quality.

Uniqlo Blocktech Parka – $69

The Uniqlo Blocktech parka is causing a stir in travel circles, and for good reason. This affordable winter coat is lightweight, durable, and packed with thoughtful features like a constructed hood to keep the zipper off your neck scruff, ventilation to keep you cool in monsoons, and adjustable cuffs to keep you dry. It’s sleek, slick, and simple. Two thumbs up.

Bluffworks Chinos – $125

These travel pants really are the best. Even in winter.


Next time you get dressed for a flight, choose an outfit you can rock well beyond the airport. As always, look for neutral and versatile pieces you can dress up with a quick shoe or accessory change. For optimal in-flight comfort, a little lycra will keep you from feeling pinched, and synthetic fibers tend not to wrinkle as easily. After all, when you arrive in a new place, don’t you want to be ready to jump right into discovering it?

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