The Investment: The Work Bag

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photo via

So you’re trekking to the office on a frozen January morning sporting your best suit, shoes, and top coat. Everything is going well until you notice what seems to be a cardboard box strapped to your shoulder. No, you haven’t become the most fashionable UPS Deliveryman, you’re just wearing a bag that makes it seem like it. It’s easy to fall in line with just any option that carries your laptop comfortably from point A to point B. I did it, with a bland, work-supplied bag that wasn’t suited for a college career fair. But like a well placed pocket square, a choice bag is another accent that can set you apart from the crowd.

To be honest, on the long list of men’s items to buy, a solid work bag is toward the bottom. Having said that, getting one is one of the most lasting investments you can make. Because they’re a functional piece, the trends surrounding bags change much more infrequently than menswear. If you get the right one, you have something that can easily last you as long as you’re on the job, in fact, my roommate uses the same bag his dad slung over his shoulder. This makes it an ideal investment piece. Two of the most common work bags available today are the briefcase and the messenger bag.


Briefcases are an endangered species; rarely do you see anyone toting one. But a briefcase is a symbol of the business world, it’s associated solely with business and that gives it a serious vibe, it makes a statement. Briefcases are simple, slim, and functional bags for carrying the essentials to work. In today’s world, that’s just your laptop. Briefcases generally come in leather or wax canvas. Leather lends itself to more formal occasions, like the workplace, while canvas also fits in a more casual environment. If you opt for leather, besure to spend the extra money for full-grain leather case. Full-grain leather has more texture andreduces the need for any sort of synthetic material to coat the outer layer of the leather, giving it a richer, stronger look. The drawback of the briefcase is space; you aren’t going to be throwing your gym clothes in it. But if you’re only going to be using this bag in the office, a briefcase may be the best option.

Filson - Original Briefcase - $265

Filson is an American company who makes some of the best briefcases out there. They may have made your father’s briefase, hell, they may have made his father’s. None of the frills of the other ones, it’s named the original for a reason. It’s made of twill, making it durable. This Filson is a fantastic investment that you’ll have for years to come.

Copper River Bag Co. - 14'' Rockport Briefcase - $167

If leather is more your thing, this is perfect for the workplace. It’s clean and elegant. The USA made Rockport briefcase is wrapped in full-grain, so you’re getting quality leather to go with a sophisticated style. It comes in eight different colors, so you can match it with your iPod Nano from 2003.

Ernest Alexander - Watson Waxed Cotton Briefcase - $375

I admit, it’s a splurge, but it’s a good one. Ernest Alexander is a new face on the fashion scene and their bags are their claim to fame. Made in New York, this simple, yet attractivecanvas briefcase canlast for decades. Coated in wax cotton, it’s one of the few cases versatile enough to  work outside the workplace. Comes in tan, grey, and chocolate. Be careful if you choose the tan colorway it will attract more dirt than the darker alternatives.

Messenger Bags

On the other hand, or shoulder, you have the messenger bag. A bit more casual, the messenger bag is still acceptable in the workplace, while also versatile enough for  other situations. Messenger bags can come in leather or wax canvas. Wax canvas is more casual, while leather is a bit more businessl, but for the most part they’re interchangeable. Here’s some of our favorites.

Ernest Alexander - Walker Messenger Bag - $345

Yes, it’s another Ernest Alexander, we swear they’re not paying us, not yet anyway. I personally own this bag and can vouch for its quality and style. It’s available in the same colors  as the briefcase above. This bag has a bit more space for you to fill it out so feel free to toss your books, booze, and other workplace necessities into the bag.     

Brooks Brothers - J.W. Hulme Leather Flap Messenger Bag - $580

There’s no denying the steep price tag but it’s one of the most handsome leather messenger bags available. The brown option is rich, but the tan really pops. This will be the bag that you hand off to your kids 30 years from now...or not.

J.Crew - Abington Messenger Bag - $98

For those of us who don’t have half a paycheck to drop on a bag. It looks great and it will certainly set you apart from everyone else carrying a standard issue bag. Speaking of standard issue, it’s available in olive and khaki cotton canvas. The reviews on this are a little suspect in regard to the quality of the bags, but J.Crew customer service has been very responsive to these complaints.

Try to pick a bag that contrasts the outfits that you normally wear; pairing a tan suit with a tan bag causes them to lose their flair.

Now, getting one of these is not at the top of list but it’s a purchase you will use day in and day out  for the next 10 years. That shelf life is much longer than many other men’s fashion items today. So invest in a bag that will carry your things as well as you carry yourself.



A lifelong Washingtonian save for a stint at the great Pennsylvania State University, Eric now resides in the D.C. area. While not one for sound financial decisions, Eric enjoys the lifestyle and the appeal of the gentleman. He loves the curiosities of life, nothing interests him like traveling to a new place, a well-made suit, house music, or unexpected adventures leading to memorable stories, that is, if he remembers. He’s also the resident bartender for What Is A Gentleman and has the bartending school certificate to prove it.