Stylish and Comfortable Travel Outfits for Airplanes and Beyond

Megan Lee

Looking nice on your day of travel is important. And not only because you’re excited and want to put your best foot forward, but also because it’s fun to pretend/convince the TSA officer that you have your life together (and regularly match your socks).

After all, when you’re fumbling to get your liquids and electronics checked, using the perfect combination of grace and efficiency, you’ll take any help you can get in the “Not a Total Amateur at Life” category.

Here are some ideas for stylish and comfortable travel outfits—from your hometown, to the airport, to your destination, and back again. Look sharp when you fly!

What Makes a Good Travel Outfit?

When it comes to travel outfit ideas, you need to focus on the big four, namely…

Style

The first key to having fashionable (and enviable) travel outfits is style! Claim your signature look by strutting with confidence and a smile. Use resources like Pinterest, magazines, and fashion blogs to stay up-to-date on the latest and most fashionable looks, but edit it to fit your style.

Comfort

Leave your stilettos/dress shoes at home (or in your backpack) and follow that slightly-more-casual approach from your head to your toes. The goal should be a relaxed style, allowing you to dress for comfort without looking like you don’t give a damn.

Quality

We all want our clothes to last years instead of weeks, right? Unfortunately, the “cheap” of fast-fashion extends far beyond the price tag. Forego throw away culture and invest in clothes that are built to last and go for timeless over trendy. 

Attention to Detail

You can be stylish. You can be comfortable. Your clothes can be purchased from higher quality brands than Forever 21 and H&M. But how do you really stand out? The answer: Accessorize! Accessories can upgrade any outfit. So think about bringing a couple pieces of “Wow” to add variety to your travel outfits, like a solid pair of Kenneth Cole Foxy King Fashion Sneakers ($80) or a pop of color à la Rag & Bone Waxed Cotton Baseball Cap ($125).

Remember: Layers are your friends. They’re essential for a well-styled, high-concept vibe.

With these four areas of focus under your belt, you’ll be rocking stylish travel outfits in no time whatsoever.

Stylish Travel Outfits for Long Flights for Women

If you have a loooong day of travel ahead of you—double digit hours long—then you need to think hard about what to wear. Your outfit can be simple or elaborate depending on your personal style, but it must be comfortable. Here are some classic travel outfits for long flights:

Ready to Race to the Gate, but Otherwise Chill

 

Start with Leggings

Choose from your go-to favorites—now is not the time to test out a new pair. Recommended: Nordstrom Zella Live In High Waist Leggings ($54)

Add a T-shirt

A heather-grey bamboo scoop tee. Look for fabric that will be doing you favors, and I love Bamboo because its a natural fabric that’s light, breathable, and moisture-wicking (keeping you fresh well into hour 15).

Recommended: Carihola ($34)

Layer on a Jacket

A neutral-colored jacket with reliable pockets is a good choice that will remain versatile throughout your trip. Even if you’re headed towards the tropics, a jacket is a must-have for comfort in-transit, or for when you cross paths with the inevitable over-blasted air conditioner. This is the perfect look for fall—swap for a denim jacket if you’re traveling in the summer.

Recommended: Banana Republic’s Lightweight Twill Utility Jacket ($148)

Wear Your Bulky Shoes on the Plane

Make sure your bulkiest kicks are on your feet boarding the plane. Pro-travelers know it’s best to wear your bulkiest items rather than pack them. Ideally, these shoes are both functional and useful, but also have (at least) a touch of style. Break them in before you go.

Recommended: Nike Revolution 4 ($60)

Accessorize!

A cute hat and other details make all the difference. Have a favorite sports team? Adore your Alex and Ani bracelets? Still wear your cherished claddagh ring? Now’s the time to tune into your personal style game and pay attention to those details.

Recommended: Chicago Cubs Hat for Women ($24)

Mix together and voila—the perfect traveling outfit.

 

Airport to the Boardroom Outfit

Start with Your Favorite Dress

You know the one, it makes you feel both comfortable and confident. I love Ponte dresses due to their sturdy, yet stretchy fabric—perfect for those accidental “I-overate-at-the-airport-Auntie Anne’s” moments. Since they are double-knit they hug the right parts. Bonus points for color blocking.

Recommended: French Connection’s Lore Lula Dress ($118)

 

Add a Cardigan

A cardigan is a versatile travel companion. Make sure its a solid color that pairs well with multiple outfits in your pack. Neutrals work perfectly, but stripes can be a fun twist (provided your dress is simple). Leave the fringe, the rhinestones, the frilly bits behind and opt for something a little more fitted.

Recommended: J Jill Perfect Short Cardigan ($40)

Slipper Shoes

No need to tire your tootsies out walking up and down your terminal. Give your feet a rest in simply, comfy slip ons. Keep your power shoes in an easy-to-access spot in your carry on (never lose sight of them) but wear cute and comfortable alternatives in the meantime.

Recommended: Lucky Brand Emmie Flats ($59)

Go for a Glam Bag

A real leather tote bag. No more breaking handles and cracked “vegan” leather—invest in ethically sourced, high quality split cowhide to keep your on-the-go bag boardroom ready and glamorous too. Make sure your laptop, tablet, and external battery pack fit seamlessly.

Recommended: Duluth Trading’s Lifetime Leather Bag for Women ($170)

You’ll be nailing your presentation for the execs faster than you can say “We are now clear for takeoff.” Polished professional, much?

Ready for Immediate Sightseeing Outfit

Start with Secret Stretch Pants

Old school jeans are too tight and yoga pants might look lazy more than stylish. Instead, invest in pants that look legit but are actually forgiving, stretchy, and wonderful.

Recommended: Uniqlo Leggings Pants ($29)

Add an Oversized Cardigan

I can’t say enough how many cardigans I’ve envied while surveying the crowd from my gate perch. It almost doesn’t matter which shirt you put under this thing. They’re so darn cute, stylish, AND cozy—perfect walking the airplane cabin runway. Winning!

Recommended: Anthropologie Harly Midsummer Textured Cardigan ($98.)

Rock the Ankle Boots

The icing on the cake is an understated, high quality boot that your stretchy pants can easily tuck into (or roll ‘em up for a more dynamic look). In summer, swap these for fashionable, but sturdy sandals.

Recommended: Hush Puppies’ Claudia Catelyn Suede Ankle Boots ($74)

Accessorize!

Add a long necklace. Up your casual top style game just a tad with some bold jewelry to round out these kinds of travel outfits for long flights.

Recommended: Gold Beaded Leaf Lariet Necklace ($15)

Pro tip: Wear outfit #1 on your way out, and pack outfit #2 for your trip home.

Stylish Travel Outfits for Men

I Woke Up Like This Outfit

Start with Tapered, Well-Fitted Sweatpants 

This look might be the closest you’ll ever get to convincing strangers you are, in fact, an A-list celebrity. I love this look!

Recommended: Lululemon’s ABC Jogger ($128)

Add a T-shirt

A t-shirt made with sweat wicking-fibers is your long haul flight BFF. Now’s not the time to wear that old 5K freebie or another workout top. Wear a t-shirt that looks like you tried a little bit. Avoide white because it definitely won’t come back from your travels white.

Recommended: Patagonia Merino Daily Shirt ($55)

Layer Up a Jacket

A field jacket looks great. Something military-esque, with lots of pockets (to help you stay organized/remember where you put your passport), and with a hint of style. Olive or charcoal colors are best.

Recommended: F2 French Field Jacket ($178)

Pay Attention to Your Kicks

Sneakers that you can dress up or down will add versatility for the duration of your trip. Long gone are the days of New Balance in white. Sneakers now have a personality of their own—make sure yours get noticed.

Recommended: Converse’ Jack Purcell ($55)

You’re relaxed yet sophisticated. Well done.

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Off to Work Outfit

Start with a Dress Shirt

Choose your dress shirt carefully. They are not all created equal. Bonus points if your dress shirt is wrinkle free and can rock both a tucked AND untucked look.

Recommended: Bluffworks Travel Shirts for Men varied pricing

Add a Tailored Blazer 

This doesn’t need to be over the top fancy, but it should fit you, and fit you right. For travel, you want something that’s packable and not quick to wrinkle. Check out Shawn’s travel blazer comparison, or so for something classy like:

Recommended: Suit Supply Havana Fit ($399)

Comfort on the Bottom

Opt for comfortable dress pants on the bottom. No, that’s not an oxymoron. Hear me out! Now might not be the time to wear your favorite, snug bottoms. Invest in a pair built specifically for business and travel so that you can breathe on the plane. Shawn compared these travel pants; another reliable option is:

Recommended: Eddie Bauer Relaxed Fit Comfort Waist Chinos ($40)

Swag Details

Men rock accessories too. A nice leather belt (bonus points if it’s reversible—hey, you’re trying to maximize use and minimize space!), your favorite watch, shoes that remind you that you can make a deal. Anything to up your look and make it feel YOU.

Recommended (go big or go home!): Garmin Fenix Chronos ($845)

A high level of comfort without sacrificing a polished look. Well done.

Vacation Vibes Outfit

Start with Brightly Colored Pants 

Let your personality shine, brother, you’re on vacay! Just make sure they fit well, feel comfortable, and can be paired with a couple other shirts in your pack, too. You could also opt for straight up white, or denim here too.

Recommended: Zioneer Pant by Prana ($50) 

Make a Statement

Adopt a wildly patterned collared shirt as your primary layer. Keep in mind you don’t want to overdo it when you pair this fun, punchy shirt with your pants. Feel free to get corny with your print—you are traveling, after all!

Recommended: Ralph Lauren’s Travel Print Button Up Shirt ($125)

Slip on Some Skids

I just love the combination of slim-fit pants and slip-on sneaks. Keep your shoes a neutral color, so they’ll be able to match other outfits in your backpack. Remember, you’re aiming to travel with just one pair of shoes.

Recommended: Vans ($55)

Shades Complete the Look

Sunglasses are the final touch that says, “I’m on vacation, without a care.” We won’t judge you for sitting at the airport terminal with your shades on… thaaaat much.

Recommended: Rayban Wayfarer ($193)

Have a little fun with your look! This one works especially well for summer travel outfits, but can be tweaked a bit to make it winter-appropriate as well. Just add a bright stocking cap.

Quick Tips for Stylish Travel Outfits on Quick Flights

If you have just a short jaunt between home and away, you can put less thought into the outfit that you wear to the airport and during transit. Shoes that are easy to slip on and slip off to make security a breeze are still highly recommended. And keep in mind that layers can tie your entire look together.

Feel free to wear something that errs less on the comfy side and more on the stylish side, if your flight is just a short one. 

As always, keep your bulkiest items on your person rather than sacrificing space in your travel backpack. It might make security a little more uncomfortable, but you’ll come to love the extra room in your pack for emergency snacks, or souvenirs coming home.

TL;DR

There is no need to sacrifice style for comfort, and you don’t have to wear yoga pants and look like a slouch on your travel day. If you want the best of both worlds on the day you fly, remember this:

  • Style doesn’t have to be uncomfortable
  • Layers are your friends
  • Wear the bulky stuff on the plane (shoes and sweaters)
  • The right accessories make everything pop

And yes, the airplane aisle can definitely double as a runway.

 

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