I'M A FREQUENT FLIER, AND THESE ARE THE 16 COMFIEST AIRPLANE OUTFITS FOR MEN — STARTING AT $34
You won't even notice you're on a red-eye.
As a frequent traveler, I can assure you the comfiest seasons to travel on a plane are fall and winter. No, it’s not because the airline seats get any bigger during this time, but rather you get to sink into said seat wearing a cozy textured sweater, plush shearling hoodie, or packable puffer coat that adds a touch of comfort and even acts as a travel blanket as you hurdle through the sky at 30,000 feet.
When the leaves turn and temperatures drop, my fall and early winter air travel style in the skies becomes a balancing act between comfort, coziness, and looking sharp. That means smart layers, cushy fabrics, and pieces that transition seamlessly from the aircraft to my final destination. Think: elevated joggers, buttery-soft sweaters, versatile sneakers and snug slip-ons, and cocoon-like jackets. Ahead, I’ve field-tested and curated some of my favorite cold-weather airport out and airplane clothes that will prepare you for any flight itinerary — and they're each under $100.
Related: 11 Frequent Fliers Share Their Go-to Travel Essentials — and They’re All Under $50 at Amazon
Eddie Bauer EB Signature Fleece Crew Sweatshirt
$70
$35
Eddie Bauer recently went through a brand refresh, and I’ve been digging its comfort-focused gear for travel days — starting with the EB Signature Fleece Sweatshirt. Available in a solid hue option and a cool logo-adorned version, it's a heavyweight for the fall and winter seasons. Its cozy fit is also made with a comfy cotton and polyester blend and is slightly oversized, which makes it perfect for slouching around comfortably in an airline seat; it even has that yummy brushed cotton feel when you touch it.
Forsake Mason Low Men’s Sneakers
$90
Easy to slip on and off and featuring a thicker, looser lace, Forsake Mason Low Men’s Sneakers make the TSA security line a breeze whether you have PreCheck or not. Featuring a stitched design and removable memory foam insoles, these shoes allow you to customize them to your exact fit and support preference. And, they're machine washable; I've put them through the washer a few times and they haven't lost their lustrous sleekness yet. This Forsake pair is perfect for indoor or outdoor adventures from the city, the park, or even the beach. With reliable sole grips and tuckable laces, it's an easy add-to-cart decision — but you'll probably have a hard time choosing between the shoe’s two handsome black or olive color options.
Cep Men's Infrared Recovery Compression Socks
$55
Compression socks are nonnegotiables for long flights, and I’ve noticed that if I bring along the right pair, they can even help me get to sleep quicker on a grueling red-eye. This pair by Cep is made with infrared technology that aids in blood flow so your feet don’t feel tired or sore, but they’re also thin and easy to wear with almost any shoe, something I’ve struggled to find in competitor compression socks. Constructed in light merino wool, an ideal but breathable material for fall and winter warmth, they’re soft to the touch and boast padded footbeds. Still, my favorite feature is how they keep your feet and toes at the perfect temperature even when the aircraft’s AC is cranked up to the max.
Lululemon Soft Jersey Long-sleeve Shirt
$68
This classic long-sleeved T-shirt by Lululemon is peak athleisure wear for a plane ride, easily styled under a vest as it is with jeans, comfy tapered jogger pants, or a pair of workout shorts. Whatever you pair it with or layer it under, its soft, stretchy jersey cotton will feel incredibly comfortable. Strerchy fabric, a discreet logo pop in the back, stitch detailing at the back neckline, and a heathered look make this one a suitcase winner, as does its range of colors including graphite gray, standard white and black, an eye-catching willow blue, and more.
L.L. Bean Organic Cotton Rollneck Sweater
$90
$80
Since I’m constantly hopping between climates, I’m always on the hunt for sweaters that can transition through different time zones and seasons, and this one from L.L.Bean does that effortlessly. Featuring a cozy roll neck and ribbed cuffs, the woven sweater is warm enough to wear under a jean jacket in the fall or a peacoat in the winter months. But since it’s made of organic cotton, it’s also breathable for those moments when you find yourself running through an airport terminal to catch a connection. This particular style comes in regular and tall fits and a large range of sizes, plus it’s machine washable so you can keep the dry cleaning bills to a minimum.
LBL Casual Half-zip Sweatsuit Set
$42
$34
Stand out among the sea of classic gray and black sweatsuits with this retro-inspired matching set that's winning over Amazon shoppers; more than 200 of them were purchased in the last month, according to the retailer. It's a complete outfit in one, making getting ready for that early morning flight a breeze. And, you can easily match the half-zip sweater with your favorite jeans or trousers when you're at your destination. The same goes for the matching joggers: wear them with that cool sweater, breezy button-up shirt, or relaxed T-shirt you packed.
Minnetonka Double-bottom Fleece Moccasins
$65
Like many men, I’m obsessed with my On Cloudsurfers for long travel days that require lots of terminal switches or hours of city walking. But when opting for something slightly more stylish but still cozy-fall or winter-appropriate, these Minnetonka Double Bottom Fleece moccasin slip-ons are the ticket. The woven-stitched nature of them, featuring a cute leather lace details, practically begs to be worn by a fire pit but they also work well for air travel. That’s because the double-bottom fleece (in a handsome red plaid pattern) makes them incredibly comfortable and warm on the feet, so I regularly find myself wearing these to the airport lounge and on the plane itself or at my house, a hotel, and even out for dinner and drinks.
J.Crew Seaboard Soft Knit Button-up Shirt
$98
$67
For those moments when I’ve got to dart from the plane and make my way to a casual meeting or business lunch, a soft knit button-up shirt is always on the pack list. You can obviously dress it up or down, but I like to wear it when I fly with a loose-fitting T-shirt underneath so I can alternate between having it open or buttoned up for a relaxed, comfortable ride. This roomy J.Crew version has a double-knit fabric that oozes softness while appearing sturdy and structured. Still, its secret weapon is that it’s also stretchy for those times when you need to do the limbo around fellow passengers in an aircraft’s crowded aisle. The deeper, front camp pockets are clutch when I need to quickly stow away items like an Apple AirPods case, a pair of sunglasses, or the pen I just used to fill out the Customs form.
Jmierr Men's Pullover Sweatshirt and Joggers Set
$43
Comfy, breathable, and stylish to boot, Jmierr's Men's Pullover Sweatshirt and Joggers Set comes in a variety of colors that will keep you looking sharp even while catching some Zs on the plane. Don’t snooze on these, though: they’re packable, washable, and built to last, so they can go wherever you’re jetting off to next. The loose-fit design allows for maximum movement, which means you’re ready to hit the ground running (literally?) when you reach your destination.
LecGee Men's 2-piece Corduroy Shacket and Pants
$46
For under $50, this stylish two-piece corduroy shacket (or shirt jacket) and pants combo from LecGee might just be the deal of the year. Featuring a rich, textured polyester blend and a variety of color choices in a cool corduroy look, it’ll be hard to buy just one set. You can travel easy knowing that you don’t even need a belt to look this good: the stretchy waistband comes with an adjustable drawstring that works for any body shape. Style the jacket open or closed, roll up the pant legs or not — you’ll look fly in the sky no matter what.
Cgrrbw Men's Chelsea Boots
$55
It’s hard to deny the reliability and versatility of a classic Chelsea boot, which is experiencing a trendy renaissance in the men’s footwear scene this fall/winter. Here, Amazon-loved brand Cgrrbw captured the casual boot spirit with a distinctly modern design, built around light and airy comfort and on-trend colors, including camel, gray, and black in suede or polished leather. This particular Chelsea boot gets high marks for comfort thanks to a rubber sole, plus it slips on and off in record-setting time with ease and can be paired just as easily with jeans and a tee as they can a leather jacket and trousers.
Cozy Earth Men’s Bamboo Pajama Joggers
$105
$84
Psst…no one has to know you’re wearing your pajamas at the airport. After all, who can tell when they’re this stylish? Cozy Earth’s Men’s Bamboo Pajama Joggers mix fashion and comfort in a breathable, soft-to-the-touch bamboo viscose blend. Even on an airplane, I can’t personally get to sleep unless I’m in light, comfortable clothing, so I regularly wear these pajama joggers for overnight travel legs when I need serious shuteye. At less than $100, you don’t need deep pockets to rock these — although the pockets are pretty deep, offering plenty of room for your wallet, passport, and phone (or the snacks from the plane). Hurry though, because they’re 20 percent off for a limited time only!
Uniqlo Pufftech Parka
$80
Create your own little cocoon in the sky by investing in Uniqlo’s elite-level fall and winter layering piece: the Puffertech Parka. This sneakily warm puffer comes in five distinctly handsome colors and never feels heavy, and it's the right choice for an airline seat since it won’t protrude onto your neighbor. Its special textured look is achieved with a “special material made by weaving two pieces of fabric together, so there are no needle holes, making it difficult for rain and wind to penetrate," according to the brand. When the weather gets temperamental, as it often does around this time of the year, the Pufftech Parka pairs those valuable water-repelling properties with a hood and pockets to keep your head and your valuables dry.
FreeFly Bamboo Shearling-lined Elements Jacket
$168
$51
Ideal for a leaf-peeping trip or early season ski trip après look, this comfy and cozy shearling-lined jacket features a hood with drawstring, front pockets, and a color-blocked look and feel. Unlike its furry-filled counterparts, this one keeps you warm without getting too toasty. Pair it with jeans or joggers for a comfy-fresh look, a beanie or baseball cap, or a trendy utility jacket if you need a little extra warmth.
Saxx Quest 2.0 Boxer Briefs
$34
Hear me out on this: When you travel, the underwear you choose really matters. This pair by Saxx proves that by offering comfort and security for your most precious cargo — and no, I don’t mean your suitcase! The Ballpark Pouch with its open fly is designed to provide frictionless support so you can travel at ease, and as one of my go-to pairs, I can attest to their comfort even in seats with the tiniest of legroom. Saxx’s Quest 2.0 Boxer Briefs are incredibly light, quick to dry, and easy to wash—even if you’re simply washing them at a campsite or in the hotel sink.
Heroic Knight Expandable Roll-top Laptop Backpack
$51
Having the right backpack on a multi-leg, extended trip with layovers can make a huge difference on your shoulders. My go-to travel backpack is the Cascade Backpack from Portland Gear, and it was the perfectly sleek carry-on that fit in everywhere I went, from the dreamy, high-style, 5-star Casa Angelina on the Amalfi coast to a rustic-chic Airbnb villa rental in Tuscany, but travelers are flocking to this new arrival from Amazon brand Heroic Knight. Its comfortable straps will make transferring from flight to flight seamless, while its streamlined frame and swift-opening roll-top closure fit under your seat and ensure you have access to whatever you need in flight.
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2024-10-28T11:11:52Z
