Street Fighter: Backpack vs. Briefcase

Today we are talking about how to make up your mind on a super divisive issue. An issue that stirs entrenched opinions equivalent to those of building walls and healthcare. An issue that has people turning against each other like the Jets and Sharks, nay, the Capulets and Montegues (shout out to Billy Shakes). We are talking about a personal decision that can define you as a man. We are talking about the age-old decision of backpack vs. briefcase.

This is really a decision between investing in pure practicality or partial practicality with added finesse and aesthetic. Backpacks are amazing. They hold everything you really need, have plenty of pockets, and save the back when heavy loads are involved. Briefcases are classic. They have been the working man’s staple toting vessel since the 1850s and present a look that says “I take myself and my work seriously.” For the sake of this argument, we are defining briefcases as any work bag designed to be carried off the shoulder, aka has a handle(s). But how do you choose? What is the best option for you? Some people swear by the backpack, while others would not dare put a back strap over their suit jacket. What is a young man to do?

There are a lot of factors that need to be considered when you decide whether to go with a backpack or a briefcase. Below is a table with scenarios and factors that should influence your decision when trying to choose between each. Tally up how many answers you identify with in each column- the bag style with the most marks is the most practical option for you.

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Not so fast! There is still one more thing to consider. The biggest decision point for choosing between Dora’s favorite accessory and the root of your Dad’s lower back issues is deciding on how you want to be viewed by your colleagues and clients. If you have zero interest in what they think and how you look, good for you! You have so much self-confidence that no schoolboy look can distract others from the great work you’re doing! You are also definitely not a consultant. If you are trying to make an impression with not just your work ethic, but your style in the office as well, consider the more professional option and go with a briefcase.

Now that you have the tools to make your decision on what style of work bag is best for you. Let’s give you some options. Below are some great bags for the long-walking, heavy gear-toting, backpack boys and some choices for the client-facing, suit-wearing, briefcase bros that will get you started on your selection for perfection.

Note: all items marked with a * mean we here at What is a Gentleman receive a commission from purchased made at that retailer to help us keep our site running.


Timbuk2 Authority Laptop Backpack

This is a 28L backpack that can fit a 17” laptop, and all of your binders, papers, and notepads. It has a separate water bottle holder and only weights 2.2 lbs, meaning most of the weight you’re carrying is your stuff, not your bag. $129

Bellroy Classic Backpack Plus

For those looking for a backpack that can keep everything separate, this Bellroy classic is the one for you. It’s a 22L pack with 5 different storage compartments. The bag is water resistant and comes with a 3-year warranty. Perfect for those who like to balance work and play. $179

Go Ruck GR1 26L Pack

Everyone has been on the GoRuck kick lately, but that doesn’t take away the fact that they make an insanely reliable backpack. This 26L backpack can fit up to 17” laptop, is water resistant, and can open completely flat for those who have a lot of electronics and go through airports often. Use it as your work bag, gym bag, or adventure bag, it can handle doing it all. $395


As a side note on briefcases: hard case briefcases have been left in the early 90s and need to stay there. That is unless you are a bond villain transporting nuclear payloads or carrying the secret formula of Coke.

KILLSPENCER Utility Attache Briefcase

This killer briefcase has all of the space and pockets you need to keep your work things in place and organized while also looking badass. The outside is leather and the inside is lined with faux fur (necessary), it can fit a 15” laptop and most importantly, it has a baggage strap so you can toss it over your roller bag handle no problem. $485


Tumi Alpa 2 Briefcase

If you are a constant traveller or a consultant looking to fit into the on-the-go culture, this is the top choice. The Alpha 2 is the bread and butter of Tumi Briefcases. It has everything you need including a laptop and iPad pocket, an umbrella pouch, luggage strap for your roller bag, and just the right amount of pockets to keep everything you need with you. $249

Ted Baker Stax Document Bag

For those who don’t carry a lot to work, all you need is a laptop, a notebook, and a couple of cords, this is for you. It forces a bit of minimalism on you but for some, that may be needed. It can fit up to a 15” laptop, and has an external pocket for your smaller extras. If you are on a budget and are fully digital, pick this one. $125

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