The older I get, the more I agree with Mark Twain that the clothes make the man—or as Shakespeare put it, “the apparel oft proclaims the man.” When you look good, you feel good, and for better or worse, the world takes you more seriously when you dress well. As an extension to Twain and the Bard’s advice, I would say that a man’s accessories—his luggage, work bag, and watch—speak volumes about his taste and professionalism.
When I started my first office job right out of college, I bought an Amazon Basics messenger bag to lug my laptop, notebooks, and Hydro Flask into the salt mines each morning. It served its purpose, but when I finally saved up for nicer threads—a bespoke suit and hand-tooled Oxfords—the polyester satchel suddenly became an eyesore against my outfit. I upgraded to the Florentine Hunter Messenger from Dooney and Bourke—a chestnut-brown leather satchel with sturdy bronze buckles and navy blue trim. Over the years, the leather has developed a beautiful patina, and I pair the bag with business-casual attire as often as I do with denim and a T-shirt.
Below are my favorite work bags in a range of prices and styles. The list includes a mix of designs—messenger bags, briefcases, canvas totes, backpacks—but all meet my criteria of superb craftsmanship, eye-catching design, and flawless functionality for the office. If the boys in ZZ Top had known about these bags, they might have sung about them in “Sharp Dressed Man.”
Gear
The 16 Best Men’s Sling Bags You Can Buy
It's time to embrace the convenience and style of sling bags for men. Before you scoff, consider this: No other bag is as versatile, whether for the gym, the office, or the plane. The trick is finding the best sling bag that hits your mark for style without sacrificing functionality…
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155 Briefcase, Gram28
Briefcases are no longer the corporate staple they once were, but there’s a reason so many style icons—the Wolf of Wall Street, James Bond, the Big Lebowski—embraced this timeless accessory. I am a staunch proponent of vintage American style—the way your hard-working granddaddy might have dressed at the IBM office—and a handsome briefcase is as timeless as a three-piece suit and pocket watch.Crafted from full-grain leather from Italy, the 155 Briefcase from Gram28 marries classic design with modern sensibilities like a laptop sleeve, iPad sleeve, and an exterior pocket for your phone. The exterior sleeve allows you to attach the bag to retractable suitcase handles. The 155 Briefcase is expensive, but each product from Gram28 comes with a lifetime warranty and a 30-day return policy.
Florentine Hunter Messenger Bag, Dooney & Bourke
Dooney & Bourke might be best known for stylish women’s handbags, but their men’s products deserve equal acclaim. The Florentine Messenger Bag boasts an Ivy-prep aesthetic—the type of satchel you might see across the shoulders of a tweed-clad, pipe-smoking professor in Harvard Yard.The bag’s understated yet luxurious design complements almost any outfit—pair it with a sports jacket, business suit, or street attire. The thick brass buckles add a touch of bling, and the hefty interior zippers are another hallmark of Dooney’s meticulous workmanship. The Florentine Messenger Bag is spacious, but the size does not feel clunky.
Jeep Collection Large Canvas Tote, Vineyard Vines
As much as the New Englander in me appreciates old-school preppy brands from Maine or Cape Cod, some of their looks are a tad stodgy—attire more appropriate for my dad at his golf outings than a thirty-something bachelor in New York City. Fortunately, Vineyard Vines, a clothing brand out of Martha’s Vineyard, combines timeless preppy appeal with a sexier, hipper aesthetic.The Jeep Collection Canvas Tote is more casual than a briefcase or messenger bag, but it serves just as well for carrying laptops and work accessories. This tote is water-resistant and perfect for the beach or picnics in addition to the office. The zip-up interior pocket safeguards small objects like phones, watches, and wallets.
Waxed Canvas Shoulder Bag, GoRuck
GoRuck, founded by a former Green Beret, crafts attire rugged enough for the outdoors yet stylish enough for the corporate wilderness. From the thick YKK zippers to the Army Duck Wax Canvas exterior, GoRuck sources military-grade materials in their Waxed Canvas Shoulder Bag. The waxed canvas, reminiscent of a Burberry hunting jacket, brings to mind a bag an English gentleman might take on a holiday to his country estate.GoRuck cuts no corners in craftsmanship, and the Waxed Canvas Shoulder Bag, available in black, tan, and brown, holds up for years even after the most punishing travel. The bag has twin exterior pockets for high-frequency items like phones or wallets and several interior zip-up mesh pockets for pens, chargers, or notepads.
Transit Travel Backpack, WANDRD
While not as dressy as a briefcase or messenger bag, a stylish backpack is the most practical and comfortable way to carry your work essentials. The TRANSIT Travel Backpack from WANDRD has a minimalist aesthetic, reminiscent of the Scandinavian design of Fjällräven.The sleek black bag looks sharp at the office, and the WANDRD TRANSIT Travel Backpack, as the name suggests, nails it as a carry-on. It’s small enough to easily slide under airline seats, and the backpack has a concealed pocket for stashing passports and AirTags. The backpack is water-resistant and has a compression sleeve to keep laptops and tablets secure even on the bumpiest flights.
Brentwood Briefcase, Parker Clay
Parker Clay, a leather goods company from Santa Barbara, California, sources sumptuous, full-grain leather from Ethiopia. You can feel good about supporting this brand, too, as a cornerstone of Parker Clay’s mission is to ensure fair wages and safe working conditions for female tanners in Ethiopia.The Brentwood Leather Briefcase epitomizes understated luxury. The rich leather is handsome enough unornamented, but the brass buckles add a just touch of flash. The bag has two handles like a traditional briefcase and also a crossbody strap for hands-free carrying. Inside, a gallery of pockets keeps files, laptops, chargers, and pens organized and easily accessible.
