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Most modern messenger bags fall into the medium-size category; their compartments are usually designed for 10- to 17-inch laptops. Once you’ve settled on the general dimensions you need, it’s time to consider style:To find the best messenger bags on the market today, we culled recommendations from all over the web, focusing on product releases from the last two years. Next, we compared these bags to 2019 “best of” lists from websites that covered technology, fashion or a combination of the two. After narrowing down our picks for each category, we weighed recent product reviews against top-selling models on Amazon.com, taking authentic customer feedback into consideration.

Made from ethically sourced buffalo leather, this handcrafted bag is meant for laptops up to 15.6 inches. The rustic, vintage style is complemented by a charcoal black finish, resulting in a distressed look that is sure to please. There are two front pockets for easy access to your essentials (keys, wallet, phone, etc.), and several organizational compartments inside. It’s the perfect bag for shuttling stuff from one meeting to another, with panache.

If a briefcase-style bag is what you’re after, there’s a lot to like about this one; Its anti-dirt design is made from top-quality crazy-horse leather. In addition to the padded laptop compartment, the bag has several zippered pockets to keep all your valuables secure, and does so in style. Bonus: The rear strap lets you easily attach the bag to rollable luggage, for all you jetsetters out there.

For a classic aesthetic with room for all your stuff, look no further than the NEWHEY Men’s Leather Messenger Bag. Made from high-quality cowhide and high-density waxed canvas, the outside is completely waterproof, allowing you full freedom to dash around town. It’s tough, too: the solid zinc-alloy rivets and buckles, combined with tensile stitching on the handle and shoulder strap, make for a powerful load-bearing combination. This two-toned bag is meant for the long haul, and the leather’s imperfections become even more ruggedly attractive over time. For less than $50, it’s a great value.

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If you’re never sure what life will throw at you next, this is the messenger bag to get. Its ambidextrous design has something for everyone, from the water-resistant 1050D Nylon construction to the integrated quick-draw compartment and reinforced enclosures. The no-slip stabilizing strap is a welcome feature, keeping the bag close to your body for balanced load distribution. There’s even a water bottle pouch, for when your hustle leaves you parched.

For the environmentally conscious, Mobile Edge offers the minimal-carbon footprint Eco Messenger bag. The dedicated laptop compartment will keep your notebook safe, and there are plenty of other pockets (including a removable ID holder) for your accessories. The velcro panels are super functional, and the rugged design should be a hit with college students and business-minded jetsetters alike.

Timbuk2 designers worked closely with their founder (a former bike messenger and inventor) to bring back his original flagship messenger. Using Cordura Nylon as its “indestructible” base fabric, the improved design features an adjustable cross-body strap, internal organizer compartment, and safety-centric reflective tails. Bonus: according to Timbuk2, the bag is specifically designed to fit a six-pack in the main compartment. Nice.

Laptop security: This one’s important. Make sure the laptop compartment is the right size for a snug fit; some manufacturers even include inner straps to keep devices in place (You don’t want your laptop smashing to the ground as you remove the bag from your shoulder, do you?). Remember to check for adequate protective padding, too.

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Shoulder comfort: If you’ll be wearing the bag on longer commutes, a comfortable strap is paramount; some shoulder straps are vertically oriented, while others are slightly angled. Padded straps are usually more comfortable, but adjustability is also a factor there. For additional stability while on the move, make sure your bag is equipped with a complementary stabilizing strap, which takes some weight off your shoulders, which is especially important for cyclists.

Weatherproofing: If you don’t plan on using the bag outside much, no biggie. But to prepare for the occasional squall, make sure your bag is properly weatherproofed. Look for overlapping flap closures, pocket cinches, waterproof zippers, and taped seams -- features that will keep your valuables dry. Nylon and canvas bags are worth a look for their excellent protection against bad weather.