Friendly Skies: 20 Best Carry-On Bags for Men

We all look forward to two-week-long vacations, the ones where you check multiple bags, turn off your phone, and go off-the-grid for such a long period of time that your co-workers begin to hate you.

Unfortunately, though, those long haul vacations are few and far between. The best we can typically hope for in terms of a break is being able to tack a few extra days onto a long weekend. And for those short trips, you pack as light as possible. Not only because the length of your trip requires less cargo, but also because you don’t want to spend precious seconds of your already-limited time waiting in the hell-hole that is referred to as “Baggage Claim” (and don’t even get us started about checked bag fees). So, in an effort to help you avoid having to check a bag, we’ve rounded up 20 of the best bags to stow neatly in the overhead compartment. Wheels up.

Everlane Twill Weekender

Everlane Twill Weekender

San Francisco-based Everlane cuts out the middle man, so you get quality-crafted items for way less than you would ever get from other retailers. This Twill Weekender is a prime example of their ethos, made from 100% water-resistant cotton twill from China, with leather accents, interior pockets, and a guarantee that it’ll fit in any overhead compartment.

Purchase: $95

Owen & Fred Work Hard, Play Hard Duffel

Owen & Fred Work Hard, Play Hard Duffel

Brooklyn-bred Owen & Fred focuses on upgrading men’s goods and adding a little playfulness to them, and the Work Hard, Play Hard Duffel does exactly that. Printed on the inside with its eponymous saying, the bag is made out of a combination of durable duck canvas and nylon, which means it’ll be your favorite companion wherever you travel this summer.

Purchase: $99

Topo Designs Duffel

Topo Designs Duffel

Topo Designs is mainly known for its rugged backpacks, but the Colorado-based company’s duffels will give the beloved backpacks a run for their money. Made from ultra-durable Cordura, the bag will stand up to whatever you throw at it, whether it’s a bachelor party in Miami or a family wedding in Washington.

Purchase: $129

Herschel Supply Co. Outfitter Bag

Herschel Supply Co. Outfitter Bag

Vancouver-based Herschel Supply Co. has a bag for virtually every occasion, but there’s no better offering for when you’re headed to the airport than its Outfitter Bag. You can carry it in several different ways—leather-lined handles to carry by hand, a padded strap to swing over your shoulder, or built-in backpack straps to haul your load on your back. The bag also has multiple interior pockets and a separate shoe compartment built into the bottom to keep sweaty feet smell away from your clean laundry.

Purchase: $130

Timbuk2 Wingman Carry-On Bag

Timbuk2 Wingman Carry-On Bag

San Francisco-based bag maker Timbuk2 (a company that was originally named “Scumbags,” no joke) makes a variety of affordable bags that can stand up to years of travel. The Wingman Carry-On bag is made specifically for long haul travel—look at it from one angle, it looks like your basic duffel, open it up, and it’s full-on suitcase. The easy-access exterior pocket is perfect for stashing your passport or tablet, but the best feature on this bag is the removable backpack straps, making it easier to maneuver through an international terminal.

Purchase: $149

Flight 001 Mt. Drew Duffel Bag

Flight 001 Mt. Drew Duffel Bag

Flight 001 specializes in creating and selling products that help streamline the travel process, and the brand’s Mt. Drew duffel does exactly that. It’s made from rugged waxed canvas with brown leather accents and a pinstriped interior for extra flair. It’ll look great next to you at the gate while you’re waiting to board.

Purchase: $200

Graf & Lantz Parker Weekender

Graf & Lantz Parker Weekender

Designers Holger Graf and Daniel Lantz are known for creating unique bags and accessories out of unique and luxurious materials. And while this Parker Weekender doesn’t use the brand’s signature material (merino wool felt), it’s still a fantastic offering. Made from soft cotton canvas with genuine leather accents and straps, it’ll be the perfect bag to take on whatever adventure you’ve got planned.

Purchase: $212

Tom Bihn Aeronaut 45

Tom Bihn Aeronaut 45

Designer Tom Bihn has been crafting rugged bags since the 1970s, and the Aeronaut is one of the best bags they have on offer. The best feature of the Aeronaut 45 is the fact that unlike most duffels, it has multiple interior compartments that allow you to separate items like your dopp kit and shoes from the rest of your gear. Available in a variety of different color combinations, this will quickly be your favorite piece of luggage. You’ll be tossing that cheap wheeled suitcase after your first trip with this guy.

Purchase: $280

J. Crew Wallace & Barnes Duffel Bag

J. Crew Wallace & Barnes Duffel Bag

Out of Wallace & Barnes—J. Crew’s vintage-inspired division—comes this classic duffel bag that takes its design inspiration from the US military. With the roomy interior and Italian leather accents, it’s the perfect bag to take on a last-minute jaunt you booked when you were feeling spontaneous.

Purchase: $358

Filson Heritage Sportsman Bag

Filson Heritage Sportsman Bag

Filson has been creating quality goods since the late 1800s, so you can rest assured that they knew what they were doing when they crafted this Heritage Sportsman Bag. Made out of rugged canvas twill that’s virtually indestructible, the bag is water-resistant, and features interior dividers to keep your stuff organized while you’re living out of a bag for a few days.

Purchase: $358

Billykirk No. 166 Carryall

Billykirk No. 166 Carryall

Brothers Chris and Kirk Bray have been crafting quality men’s accessories since 1999, and their No. 166 Carryall is no exception. The rugged bag is made from a combination of US-sourced waxed canvas and leather and features a bonus leather luggage tag that is monogrammable for an extra $15.

Purchase: $374

Ernest Alexander Andrews Weekend Duffel

Ernest Alexander Andrews Weekend Duffel

Ernest Alexander was started 5 years ago with the mission to create the perfect men’s messenger bag, and since then, the brand has been churning out quality men’s bags perfect for work and play. The Andrews Weekend Duffel is roomy enough to fit everything you need for a long weekend. We like the various interior pockets and the large exterior zipped pocket, but we especially like the built-in compartment for your shoes. Divide and conquer.

Purchase: $395

Ralph Lauren Winston Denim Duffel

Ralph Lauren Winston Denim Duffel

Just like your favorite pair of jeans broadcast the message “I’m not working today,” this Winston Denim Duffel from Ralph Lauren also says “I’m off-duty.” Casual but handsome, this denim and leather bag is perfect for whatever low-key weekend getaway you’ve got planned.

Purchase: $395

Killspencer Weekender 3.0

Killspencer Weekender 3.0

Los Angeles-based Killspencer’s jetblack Weekender 3.0 bag will inject a little rock ‘n’ roll to wherever you’re headed. Made out of bullhide leather, the bag sports a compact silhouette but is deceivingly spacious. If you’re an expert packer, you could fit five days worth of stuff in here.

Purchase: $675

Miansai Monroe Weekender

Miansai Monroe Weekender

Miansai became the darling of the fashion world a few years back, when people couldn’t get enough of its preppy rope bracelets. The brand has since expanded its line to include other accessories, and this Monroe Weekender is one of its best. Made with a combination of durable nylon and dark brown Italian leather, the bag is mega-structured, making it the perfect bag to bring to work on a Friday and head straight to the airport with.

Purchase: $675

Skagen Riis Duffel

Skagen Riis Duffel

Denmark-based Skagen makes a variety of products, but it’s their bags in particular that embody minimalist modern Danish design. This Riis leather duffel is the perfect carry on, featuring interior pockets to store various sundries like your headphones, wallet, passport, and the like, exterior straps to hold a rolled up magazine or umbrella, and an expandable top zip to provide additional space if you get carried away with buying souvenirs.

Purchase: $745

TUMI Astor San Remo Leather Duffel

TUMI Astor San Remo Leather Duffel

For years, TUMI has been a trusted brand when it comes to luggage, which is why you see so many TUMI outposts in airport terminals. This sophisticated all-black duffel is perfect for a business trip, and is overhead storage compliant, since you don’t want to be the guy that holds up his boss at baggage claim because he was forced to check his bulky carry-on by the gate agent.

Purchase: $795

TUMI Alpha 2 Wheeled Garment Bag

TUMI Alpha 2 Wheeled Garment Bag

While we’ve stayed away from wheeled luggage as rule, we’ll make an exception with this offering from TUMI, which is made from ballistic nylon. Functioning as a garment bag (which has an interior hanging system that fits at least one suit), it has a ton of exterior pockets and two removable mesh pouches that can function as your toiletry kit. Next time your boss asks you to go on a last-minute business trip, you’ll be ready.

Purchase: $840

Hard Graft 1st Edition Travel Bag

Hard Graft 1st Edition Travel Bag

London-based Hard Graft is committed to using the very best materials to create quality accessories, and this 1st Edition Travel Bag is no exception. Utilizing blue leather, Portuguese wool, and Italian wool felt, the bag snaps open to reveal two open compartments on either side of the main zippered compartment, allowing easy access to books, magazines, and your tablet without forcing you to show off your underwear to the entire terminal. Trust us, this gorgeous bag will get you the most compliments, whether you’re at the gate, on the plane, or cooling your heels at the airport bar after a flight delay.

Purchase: $1,085

WANT Les Essentiels de la Vie Douglas Holdall

WANT Les Essentiels de la Vie Douglas Holdall

Recently founded by two Montreal-based twin brothers, WANT Les Essentiels de la Vie specializes in creating quality travel accessories that will make traveling an art again instead of a chore. This all-leather bag (available in brown or black) has four interior pockets with snap closures, a detachable shoulder strap, and a built-in exterior luggage tag. And while the price tag on this bag is pretty hefty, it’s a bag that you’ll have for years.

Purchase: $1,495

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