24 Effortlessly Stylish Fall/Winter Airport Outfits for Jet-Setting in Comfort

 

Traveling during the fall and winter months means one thing: balancing style with comfort as temperatures drop.

Whether you’re heading to your next adventure or just want to make an impression during your travels, planning an airport outfit takes a little thought.

But don’t worry, I’ve got you covered. Let’s explore the art of airport fashion for fall/winter and ensure you’re comfortable, chic, and ready for takeoff!

 

 

Things To Consider When Planning a Travel Outfit

When piecing together your perfect airport outfit, you’ll want to prioritize comfort and practicality without sacrificing style. Here are a few key things to consider:

• Layering: Fall and winter airport outfits are all about layering. Think cozy sweaters under a chic coat that you can easily remove when indoors.
• Comfort: Remember that you’ll be sitting for long hours, possibly in cramped conditions. Loose-fitting clothes and comfortable shoes are a must.
• Easy Security Checks: Stick to pieces that are easy to take off and put back on when going through airport security—like slip-on shoes or minimal jewelry.
• Functional Accessories: Don’t forget a large carry-on or tote to keep your travel essentials handy. Bonus points for a stylish weekender bag that ties your look together!

Note that I have covered travel outfits for a variety of destinations from Iceland to Italy to Seattle, Miami, Chicago and more. Now, let’s dive into some fall/winter airport outfit inspo to inspire your next jet-setting adventure!

 

 

Chic Fall/Winter Airport Outfits

For additional inspo check out my other post on summer airport outfits I did in the summer.

 

Casual Grey Sweat Set with a Long Coat

Keep things simple and practical with a soft grey sweat set, layered under a sleek black coat for that extra warmth.

This outfit is perfect for staying cozy without looking too casual, and the structured coat elevates the laid-back look.

Classic New Balance sneakers ensure comfort for long walks through terminals, while a black carry-on is both functional and stylish.

 

 

ALSO SEE: Chic New Balance Outfits

 

Neutral Layers with an Oversized Blazer

This outfit brings together neutral tones for a sophisticated look, perfect for a stylish yet effortless airport appearance.

The oversized tan blazer layered over wide-leg trousers creates a relaxed silhouette, while the cozy brown turtleneck underneath keeps you warm.

A plush quilted tote adds texture and functionality, ideal for carrying your travel essentials. The chunky platform loafers ground the look, adding both comfort and style.

 

 

Olive Leggings and Oversized Blazer

For an airport-ready look that blends comfort with chic vibes, this outfit combines olive green leggings with a sharp black oversized blazer. The black Saint Laurent crossbody adds a luxe touch, while white sneakers keep things practical and perfect for travel.

The green New York Yankees baseball cap ties the look together and adds a sporty flair. The standout accessory? A large black Marc Jacobs “The Tote Bag,” making sure all your essentials are in one stylish carry-on.

 

 

Ribbed Knit Set with Luxe Accessories

For those who crave comfort without sacrificing style, this ribbed knit matching set is the ultimate travel ensemble. The soft, relaxed fit makes it perfect for long flights, while the matching wide-leg pants add a chic touch.

Paired with a designer handbag and a sleek Louis Vuitton duffle, this look elevates airport fashion to new heights. Top it off with a black baseball cap for a casual edge.

 

 

Cozy Sporty Look with Headphones

This laid-back outfit screams comfort with its matching grey sweat set, ideal for those early morning flights. The oversized hoodie and sweatpants combo creates a cool, relaxed vibe, while the New Balance sneakers keep it practical.

A striped Miu Miu tote adds a pop of color and a fashion-forward twist. The black baseball cap and large headphones pull the look together, perfect for staying comfy and in the zone during long layovers.

 

 

Elegant Chic in a Tweed Jacket

For a polished and elegant airport look, this outfit pairs an off-white boucle tweed jacket with silky white trousers. The monochrome palette is effortlessly classy, while the tailored cut of the jacket brings structure to the look.

Paired with a small Chanel handbag, this outfit is perfect for the traveler who never sacrifices style, even at 30,000 feet.

 

 

Tailored Blazer with Knee-High Boots

Elevate your airport style with this sophisticated ensemble. A classic beige blazer over a black turtleneck and slim black pants offers a timeless look, perfect for transitioning from the plane straight to a business meeting.

The knee-high black boots not only add drama but are perfect for fall and winter weather. A black mini crossbody bag adds a modern touch while keeping your essentials secure.

 

 

Casual Jeans with a Sweater Vest

This laid-back look pairs wide-leg black jeans with a white graphic tee for an effortless vibe. Throwing a cream knit vest over the shoulders elevates the outfit just the right amount.

Paired with comfy sneakers, this ensemble is perfect for jet-setters who want to stay comfortable yet stylish.A structured designer crossbody bag and large black suitcase bring it all together, making it an easy option for travel days.

 

 

Oversized Hoodie with UGG Slippers

This relaxed and ultra-comfy look pairs an oversized white hoodie with classic black leggings for the perfect travel day outfit. The cozy UGG slippers and white socks add warmth and style, while the black baseball cap completes the laid-back aesthetic.

Toting a designer Louis Vuitton carry-on, this outfit is both functional and fashionable, making it ideal for long-haul flights.

 

 

ALSO SEE: Chic & Cozy Uggs Outfits

 

Teddy Coat with Luxe Dior Accessories

For a luxe take on winter airport style, this outfit features a cozy teddy coat layered over a hoodie and leather leggings. The sneakers add an element of sportiness, but the standout accessories take the look to the next level.

A Christian Dior oversized tote and crossbody bag add a touch of designer flair, ensuring this look is both high-fashion and travel-ready.

 

 

 

Fuzzy Jacket with Sweatpants

This look is all about the cozy factor! A soft beige fuzzy jacket is layered over light grey sweatpants for a casual, comfy vibe.

The platform UGG boots are perfect for those chilly airport floors, and the oversized headphones add a touch of cool-girl attitude. A crossbody brown bag completes the look, keeping your hands free as you juggle your luggage.

 

 

Camel Coat and Black Leggings

A fall/winter staple, the camel coat paired with black leggings is the epitome of airport chic. The long beige coat adds structure and elegance, while the leggings keep it casual and comfortable.

UGG boots and a black baseball cap give this outfit a sporty touch. Add a designer carry-on and you’re ready for the runway—airport or fashion!

 

 

Shearling Jacket with Earmuffs

Winter-ready and chic, this outfit features a cozy black leather shearling jacket layered over black leggings and UGG boots.

The oversized black tote adds functionality, while the Chanel earmuffs bring a stylish, playful touch.

This look is perfect for those jetting off to colder destinations, combining warmth and comfort without compromising on style.

 

 

Knitted Dress and White Blazer

For those looking for a chic, feminine option, this ribbed knit midi dress in neutral tones is a great pick. Layered under a white blazer, it’s perfect for creating a sleek silhouette that’s still comfortable for travel. Add a large straw tote and designer slides for a luxe, resort-ready vibe as you head to your destination.

 

 

Black Bomber Jacket and Neutral Pants

Elevating the classic black bomber, this outfit pairs it with neutral high-waisted pants and chunky white sneakers for a polished yet relaxed look.

The black top underneath keeps things simple and sophisticated, while the black crossbody bag adds structure and functionality. The oversized suitcase makes this the perfect airport ensemble for someone traveling with style and practicality in mind.

 

 

Oversized Blazer and Sheer Tights

For a daring yet cozy airport outfit, an oversized black blazer over sheer tights makes a statement. The suede platform UGG boots add comfort and edge, while oversized headphones create a trendy tech-forward vibe.

The mini beige crossbody bag is the perfect accessory for quick access to essentials. With a polished suitcase in tow, this outfit mixes high fashion with laid-back comfort, ensuring you stand out while staying snug.

 

 

Trench Coat with a Fanny Pack

For a modern yet functional look, throw on a beige trench coat over a black sweat set. The trench adds a touch of sophistication, while the black fanny pack worn across the chest keeps it casual and convenient.

Paired with white Celine sneakers, this outfit is perfect for running through airports while staying on-trend.

 

 

Relaxed Sweatsuit with Layers

For those who prioritize comfort, this matching grey sweatsuit is the ultimate fall/winter travel look.

The oversized hoodie paired with wide-leg sweatpants feels cozy and casual. The layered white shirt peeking out from beneath adds dimension to the look.

Completing the outfit with chunky sneakers and a large black tote, this is the perfect ensemble for travelers who want to stay comfy without sacrificing style.

 

 

Beige Lounge Set and Camel Coat

For a polished lounge look, this outfit pairs a beige matching lounge set with a structured camel coat.

The sophisticated layering of textures creates an elevated, cozy vibe. Simple white flats add a touch of elegance, while the large tote and silver carry-on balance practicality with luxury.

This outfit is perfect for travelers who want to step off the plane looking effortlessly chic.

 

 

Denim Jacket and Classic Sneakers

This airport look is all about effortless style with a casual twist. The blue denim jacket layered over a basic grey tee creates a classic travel look that’s both functional and stylish.

Black leggings keep the outfit comfortable for long flights, while chunky white sneakers add a sporty touch and ensure all-day comfort. The standout piece is the chic Dior saddle bag, adding an element of luxury to the laid-back outfit.

Paired with matching white and tan luggage, this look is perfect for the traveler who wants to combine practicality with a bit of high-end fashion.

 

 

Cozy Layers with a White Wool Coat

For those chilly fall and winter travels, this outfit nails cozy chic. A soft, oversized white wool coat drapes beautifully over a grey hoodie and matching leggings for a monochrome moment.

High-top Converse sneakers add a casual, yet stylish edge, perfect for walking through the airport. The grey baseball cap keeps things cool, while the cream-colored weekender bag is both functional and elegant, completing the look effortlessly.

 

 

When it comes to fall/winter airport fashion, it’s all about the balance of comfort and style.

Whether you’re going for a cozy sweat set or a more tailored approach, these outfits will keep you looking chic and feeling great from check-in to baggage claim!

What’s your go-to airport look? Let’s chat in the comments below!