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What to Wear on a Red-Eye Flight: Fashionably Comfortable Apparel for the Long Haul

Sometimes the red-eye flight is the best option, sometimes it’s the only option, and when you live on the West Coast and need to get to the East Coast, it’s what you do. There really isn’t anything comfortable about travel these days, and aside from paying a premium for better seating, your only option comes down to how you handle yourself when you do travel. You should look put together for any number of reasons, and shouldn’t be wearing the same outfit you wear every Sunday during football season, all season, without a wash. Lucky for you, there are clothing and accessories out there suited for red-eye travel, providing comfort and style.



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When it comes to long flights you have to dress the part, which means dressing comfortably without looking like a slob. The Buck Mason Brushed Loopback Hooded Sweatshirt has all the style points to turn an eye and a comfort level no basic economy middle seat could impede upon. The French terry construction is durable and warm, and promotes ventilation to keep your core at the perfect temperature. And like a fine bottle of wine, the Buck Mason Sweatshirt’s comfort and appearance gets better with every passing day and wash.

If you’re in the unfortunate circumstance where you’ll be walking down the jetway and straight to the office, you’ll need a versatile button-down for travel and boardroom negotiations. The Lululemon Masons Peak Long Sleeve Shirt is composed of a soft, light, and wrinkle-free material that looks first class through and through. And when you don’t have time to squeeze in a shower before the meeting, the “no-stink” zinc technology built into the fabric fights off odor — yours or any smell you picked up on the plane.


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When you’re traveling through the night and locked in your seat for hours upon hours, you’ll need a pair of trousers that both present seven-digit number acquisition and ultimate comfort for your derriere. The Public Rec All Day Every Day Pant (ADED) has the comfort level of your favorite sweatpant but with style acceptable for the public. The ADED has an elastic waistband with internal drawstring, faux front fly, and a tapered finish that makes this pant suitable for making new friends at the terminal bar, catching a few coveted hours of sleep, and leaves you ready for just about any forthcoming adventure.

If an 8 a.m. meeting awaits following your red-eye arrival, the Rhone Commuter Pant is simultaneously seat 14B- and corner office-compatible. The Japanese warp-knit fabric provides ample maneuverability to find the perfect sleep position within your tight quarters and looks perfectly matched with a pair of wingtips. The Commuter Pant is built for comforted travel with a security zipper pocket, snap fly, media pocket, and a gusseted crotch. In and out of the office and NOT forming a group outside the lavatory, the Rhone Commuter Pant is the TSA Pre pant you need and want.


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Perhaps the most important piece of the puzzle and never exposing toes is red-eye-suited footwear. The Vivobarefoot Gobi ll Canvas are vegan, feature the thinnest and most durable outsole on the market, and are all things comfortable. They’ll look great on your feet, even if you forget you’re wearing them, and if Jerry spills his cranberry juice, the Gobi lls are “pretty damn close to waterproof.” The Gobi lls will provide the comfort and breathability you need to keep your shoes on and if your travels take you from the beach to the tundra these Vivobarefoots are weather resistant.

From a groggy wake-up, grabbing an extra at Dunkin Donuts outside baggage claim and to Thursday’s sales meeting, the TOMS Preston Dress Shoe steps in stride. The dual-density footbed is like a pillow under your arch providing all day and all flight comfort. The Pretson is built on a business casual motif and comfortably fits under the seat in front of you. So when life is more formally waiting for you once you’ve reached your final destination, the TOMS Preston Dress Shoe is for you and One for One.

Eye Mask

Bluetooth Sleeping Eye Mask Sleep
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When you’re flying overnight and trying to get as much sleep as possible, sometimes you need a little assistance to block out the emergency aisle luminance and Bob’s overhead reading light. Thankfully, the Joseche Bluetooth Sleep Mask is standing by to accompany your hoped-for few hours of sleep. The mask is composed of velvet and cotton for ultimate comfort and has a Velcro strap in the back for adjustability. The Bluetooth has nine hours of battery life and is compatible with music and phone calls, because who doesn’t want to talk on the phone in the dark? The Joseche Bluetooth Sleep Mask will help you count the sheep and always leaves Zoro jealous.


Trtl Travel Pillow
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It doesn’t seem possible to look cool using an airplane pillow, but sometimes comfort does override style. The Trtl Travel Pillow is “the first fully adjustable travel pillow.” And unlike other pillows that look like you’re wearing a bedpan around your neck, the Trtl Travel Pillow is relatively sleek and looks like you’re just wearing a scarf to keep warm. The adjustable support is hidden within the breathable mesh fabric with lush foam padding and microfleece lining for maximum comfort. You can wear the Trtl Travel Pillow on the left, on the right, and even in the back, proving it’s the perfect companion for those not so luxurious coast-to-coast red-eyes.


Bose Noise-Masking Sleepbuds
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Crying babies, talking neighbors, and maybe flushing toilets if you’re in the last few rows of the plane — you need something to block out the world and get you through the long flight with aural pleasure. The Bose Noise-Masking Sleepbuds are specifically engineered to bring tranquility to your nighttime adventures with wireless comfort, sound blocking design, and a built-in alarm in case you don’t hear the landing gear dropping. And it should be mentioned, although these Sleepbuds will not stream your favorite nighttime lullabies, they do come with preloaded sounds of the forest, cascading waterfalls, and rustling campfires to nestle you into red-eye hibernation.

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Ben Hitch
Former Digital Trends Contributor
Ben Hitch, well, he's the first of his name and one hell of a character. You can find him exploring the streets of San Diego…
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