The Best Travel Bags to Carry You Through this Holiday Season And Beyond

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Watching how people travel—particularly how they get through airports—is one of our favorite spectator sports. There is the inevitable rush of guys bearing backpacks with corporate logos from the last conference they attended. There’s the status-hungry crowd whose bags must feature a completely different kind of logo: Usually big, bold, and brassy. Then there’s the opposite extreme – the ones with belongings crammed into a food co-op or public radio reusable shopping bag, a duct taped-together, mysterious-looking bundle, or the ones we just don’t get, who walk on with nothing in hand except maybe a book or a bottle of water. 

Somewhere among all of these holiday travelers is you, arriving just early enough to have a glass of wine pre-flight, wearing a neat, but comfortable, outfit, and carrying a bag—like one of those below—that is handsome, useful, and intelligently packed with everything you’ll need for the flight. Most of these bags are so well-designed, in fact, that they’re likely to become your every day carry. 

Mack Weldon Ion Convertible Backpack – $148
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Easily converting from a backpack to a shoulder bag, the Ion somehow incorporates nine compartments into its skinny shape, including spaces for laptop, shoes, etc. It’s been dubbed the “Ion” for it’s antimicrobial silver interior lining. A luggage sleeve, non-slip rubber handles, and water-resistant fabric and zippers round out the travel offerings, but there’s also a handy mobile device charger that stows into an easily accessed front pocket for good measure.

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Herschel Rolltop Backpack/KKtP – $129
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A collaboration between Herschel—one of our go-to heritage-style bag companies—and Shanghai-based streetwear designer Kim Kiroic, the rolltop style offers an updated take on a classic backpack. Roll up the top for easy access and to create a larger interior. Roll it down when you need less. It’s perfect to stash a down jacket or sweatshirt, or if you’ve picked up a few extra souvenirs on your trip.

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Wellington & Cromwell Hatch Briefcase – $175
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The Hatch features truly classic styling with a vintage appeal. The clamshell opening makes it easy to access the entire interior of the bag with its wide mouth, but closes tightly to maintain a thin silhouette. The side pocket is, again, a great place to stash travel documents, but because it’s gusseted, it’s also an excellent place to put that TSA-friendly clear bag of liquids. It also fits a laptop, which is a bonus for business travelers.

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Away The Everywhere Bag – $195
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Performance nylon means this bag is lightweight, yet tough, and ready for all your carry-on needs. The clean silhouette is reminiscent of a doctor’s bag, but with a large interior space. There’s a laptop pocket and organizer area for notebooks and documents, but some of our favorite features are “hidden,” including a zippered, waterproof umbrella pocket, a mobile phone pocket, and an exterior zippered pocket that is actually a sleeve to slide the bag over the extended handles of a wheeled carry-on.

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Peak Design Travel Backpack 45L – $300
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The Travel backpack’s straps stow away to keep them out from under foot on the plane or when checking the bag. The main compartment is accessible from either the front, back, or even the sides. All openings have weatherproof strips. The bag can expand for more storage. The Peak Design team seems to have thought of everything the modern traveler needs and what hasn’t been included in this bag—tech pouches, camera cubes, toiletry kits—is available on the site and designed to coordinate perfectly.

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Hook + Albert The Getaway Black Leather Duffle – $375
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Hook + Albert already had us with their famous garment weekenders, but they’ve gone one better with the Getaway duffel. It’s got a “half-moon shaped” rise built into the top of the bag to provide a secure place to drape a jacket or tuck an umbrella between the handles when you’re on the go. Side compartments stow laptops, tablets, and headphones, while a roomy main compartment has space for all other necessities.

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Stuart & Lau Regimen Gym Bag – $395
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OK, yes, ultimately, this bag was designed for the gym. But we love utilizing all of its delightfully organized sections for travel, too. For a quick overnight business trip, wear your sneakers for the flight, then tuck a pair of dress shoes into the bottom shoe compartment. Use the swiveling locker hook to hang the bag up in the hotel closet. No need to unpack. There’s even a padded laptop section and pockets to keep chargers, cords, and the rest of your gear organized, too. 

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Korchmar Dylan Computer Leather Briefcase – $425
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The Dylan features minimal, almost severe styling in a truly classic briefcase that includes an interior laptop pocket large enough to hold up to a 15-inch computer. Use the outside zipper pocket to keep passport, travel documents, or a magazine handy. It also includes a shoulder strap to sling it over your back if you’re juggling another carry-on or a coat.

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This is Ground Venture 2 Backpack – $925
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For the ultimate in precision packing, the Venture 2 offers a front-zipped “Pod” featuring spaces for phones, notebooks, writing implements, cord management, or passports, interior pockets for laptops or iPad Pros (including a section optimized for the Apple Pencil stylus), and even a hidden pocket for a Tile or other bag tracker. The company also makes special packs designed to stack perfectly into the backpack’s interior for extreme organization. 

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Adero Smart Tags Starter Kit – $119
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OK, packed and ready to go? Did you remember your toiletries kit? Your headphones?  Your phone, smart watch, and computer chargers? The Adero Smart Tag system will make sure that you’ve got all that together, and so much more. Simply attach a tag to everything you normally leave the house with—for travel, the gym, work, school, etc.—and set up reminders in the app. Give a quick squeeze to the smart tag before you walk out the door and a green light means you’ve got everything you need for the flight. A red light? Check the app for the missing camera, shoe bag, or epi-pen.

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With your travel bag in the bag, take some time to find the right outfit to wear for the trip.

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