For 18 months spanning from 1860 to 1861, the Pony Express carried telegraphs and mail from the East Coast to the West Coast faster than any other service at the time.
To start the run, a rider would leap onto a horse with a bag full of letters and ride to the next station, where the bag would be passed to the next rider.
Believe it or not, this where messenger bags got their start. Worn over one shoulder with a strap that goes across your chest, the design made the rider-to-rider transfer an easy one. Made of canvas or leather, the bags were so durable, it was said the horse and rider would perish before the bag.
The colorful history of messenger bags continues as they also proved useful during WWII. Durable and roomy, these bags were used by medics to hold medicine and food while keeping their hands free.
You probably won’t be galloping from station to station on your pony anytime soon, but the ever-practical messenger bag stays popular in the corporate world as well as among students and cyclists. A common sight in any urban area, it’s fashionable, practical, and versatile. Here’s a look at some of the best leather messenger bags for men of all walks of life.
East/West Messenger by Shinola
A modernized version of the traditional messenger bag, this bag works equally as well for short forays into town or cross-country treks. It’s made from Navigator leather, which distresses well over time. Scratches rub out easily, however, and the leather is very low-maintenance.
The bag also features a front flap opening, an adjustable strap, and pockets of various sizes where you can store your computer, tablet, book, phone, and more. Shinola runs a watch factory, leather factory, and bicycle workshop in Detroit — and their working hard to revitalize the city.
Oliver Messenger by Frye
Frye makes boots, shoes, and bags out of premium-quality leather. Founded in 1863, the company now partners with Feeding America, the largest hunger-relief organization in the USA.
Frye’s Oliver messenger bag comes in two types of leather (textured and polished) and two colors (dark brown and slate). The bag includes a long carry strap, eight interior pockets, and has a magnetic closure. The exterior is polished, burnished, and durable — this thing won’t deteriorate over time.
Colombian Leather Flap-Over Messenger by Samsonite
Samsonite offers the Colombian Leather Flap-Over as a reasonably priced, quality bag made from natural cowhide. Since the leather is minimally treated, no two bags are alike. An organizer under the front flap can hold anything you need to access quickly, and the shoulder strap is both removable and adjustable.
The bag can hold a laptop up to 15.6 inches. It also features a removable compartment for your cell phone and a pocket made specifically for an iPad or tablet. Choose from brown or black and enjoy the antique brass hardware adorning the exterior of the bag.
Manhattan Convertible Slim Messenger by Coach
The Manhattan Convertible Slim Messenger, which comes in dark saddle and black antique nickel, comes with the option of a free monogram. The bag is inspired by the easy sophistication of New York City.
Made from sport calf leather, it’s lightweight with a secure interior tech pocket and a slip handle for use as a clutch. Coach is a design house that works to define modern luxury, and this bag says it all.
The Prince Street by ONA
Based out of New York City, ONA creates fine bags and accessories for creative professionals. Their bags are stylish but still functional, and the Leather Prince Street is no exception. The Prince Street is handcrafted from full-grain Italian leather and comes in eight colors, including camo.
The bag can hold an 11-inch laptop or tablet, a camera, a few camera lenses, and other miscellaneous small items. Side weather flaps keep your gear safe and dry.
Loreto Messenger Bag by Nisolo
Carry your books, laptop, and papers with ease: Nisolo’s Loreto Messenger Bag is both fashionable and comfortable. The bag comes in two colors: chestnut and waxed canvas. It’s a reasonably-priced option for a student, professor, or anyone else in need of a messenger bag.
The Loreto is handmade in an ethical factory in Leon, Mexico. Nisolo makes leather products, such as shoes and bags, with sustainable materials. The company recommends taking steps to clean and preserve your leather products, such as caring for products with cleaner, brushes, and creams.
Colombian Leather Slim Messenger by Kenneth Cole Reaction
Made of a full-grain Colombian cowhide leather with a fully lined interior, the Colombian Leather Slim Messenger weighs in at a light 1.8 pounds and provides ample space for everything you need to carry. The main compartment can hold a laptop up to 15.6 inches, and other pockets fit a cell phone and other files or devices.
The bag has a top handle and an adjustable shoulder strap. You can also access items through an open pocket on the rear exterior. Kenneth Cole makes clothing, footwear, accessories, and more.
Vintage Messenger by WP Standard
Described as “a tribute to antique postal bags,” the Vintage Leather Messenger has been updated with a more modern and sleek messenger design. Customizable with a monogram up to three letters, the Vintage Messenger comes with free ground shipping. The Vintage Messenger includes two interior pockets, two external pockets, and a lined laptop compartment with a safety strap.
The bag also features a comfortable shoulder pad and a key lanyard. It’s made of 100% full-grain vegetable tanned leather that gets better with age. WP Standard prides itself on offering leather bags, belts, and other accessories of only the highest quality.
Stephen Messenger by Go Forth Goods
The Stephen Leather Messenger Bag is simple and durable, but still stylish. Backed by a lifetime guarantee, it’s crafted from full grain oil tanned leather that matures with age. Its water-resistant, low-maintenance and needs oil just once a year to maintain it’s classic looks. You can also customize the bag with your initials for free.
The Stephen comes in mocha, saddle, or black. Its adjustable shoulder strap and top grab handle are both made from the same full grain leather, and the bag can hold a 15” laptop as well as other items. Go Forth makes leather goods in Marietta, Georgia and gives 10% of their profits to nonprofits.
Benjamin Messenger by Will Leather Goods
Functionality is the key feature of the Benjamin Messenger, but that doesn’t mean it skips out on style. The full grain Italian leather is beautiful and easy to care for: if it gets scratched, just rub the leather with your fingers and any marks will disappear. The bag includes a pillow that’s great for travel, and the bag can be worn either as a shoulder bag or across your body.
The Benjamin is reasonably priced, and each purchase of the bag donates $7 to Will Leather Goods’ goal of donating 100,000 bags to Kids Across America by 2025.
Weatherproof Leather Original Briefcase by Filson
Filson has been around since 1897 and is the leading manufacturer of goods for “anyone who refuses to stay indoors.” This best-selling briefcase is expensive, but worth it. It comes in a rich brown shade with the option of adding embossing.
The bag is made with a special boot-grade leather that resists both weather and salt water and includes beautiful brass hardware and a felt-lined shoulder strap, with an internal divider to separate electronic devices and tools. The briefcase works equally as well for casual or formal settings.
No. 1860 Express by Holtz Leather Co.
Holtz Leather Co. created a one-of-a-kind bag that can be carried as a backpack as well as a messenger bag. The No. 1860 Express is made from full grain American leather in Huntsville, Alabama. It’s durable and roomy, with ample space for anything you need to carry.
The bag has solid brass hardware and has gone through extensive testing to become the best version it can be. Holtz Leather Co. is a family company that values heritage, tradition, honor, and hard work.
Washed Messenger by Bosca
This rich brown messenger bag with a raw interior finish is spacious and fashionable. Locking antique brass hardware adds an extra shine, and the strap offers two adjustment points. The Washed Messenger even features rubber feet for shock absorption.
Inside, the main compartment of the bag includes a lanyard for keys. The rugged but refined messenger bag is filled with other pockets, too, including an easy-to-reach zippered pocket on the back. Bosca was founded in 1911 and makes original, ingenuitive, and durable products.
Sackett Messenger Bag by Moore & Giles
This five-star leather briefcase is perfect for the corporate world. Polished and sophisticated, the three-pound bag fits a 17” laptop perfectly and can be personalized with initials for a small additional cost. The Sackett is made of Titan Milled leather, an Italian leather that includes both vegetable and chrome tanning for a burnishing effect that makes for a timeless look.
Featured in such publications as Food & Wine, The Wall Street Journal, and Cool Hunting, Moore & Giles was founded in Virginia in 1933. The company makes luxury leather products for the high-end interior design, hospitality, and aviation industries. Moore & Giles has been making bags since 2007.
Signature Stripe Messenger Bag by Paul Smith
Designer Paul Smith has created this black pebble embossed leather messenger bag as a unique and sophisticated choice to carry your belongings. The bag includes a “Signature Stripe” webbing insert running through the center of the bag.
It has a padded laptop compartment and comes with a black Paul Smith dust bag. The price is around the same figure as many of the other choices on this list and includes free shipping.