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.”
