There was a time earlier in my life when I thought, “Man, if I ever start carrying a briefcase, shoot me.” To my younger self, it was a symbol of corporate conformity, complacency, and a case of the same old same olds. Not necessarily an image a young creative wants to project. Nowadays, of course, much like the resurgence of menswear amongst a new generation of style-conscious men, the briefcase embodies and reflects something different than it used to. Sure, you can still get that boxy and bulky version with the combination locks, but with all the slimmer and sleeker options available now, there’s no reason to have to look like the boring company man.

Briefcase - He Spoke Style

As with any bag, a briefcase should reflect your style as well as your lifestyle. If you’re in business, have a job that requires you to wear a suit, or just like the look and feel, a leather briefcase is the way to go. For one you’ll carry everyday, I recommend choosing one in brown. It’s much more versatile than black, which I find to be very formal.

A canvas briefcase is a less formal option that’s perfect for the student, creative heading to meetings, or guy who’s got a computer, papers, and supplies to carry around for the day. For me, a canvas briefcase is similar to the messenger bag in terms of being a more casual bag option, but still comes across as a bit more dressed up.

Briefcase - He Spoke Style

| WEARING | QG Custom suit (similar HERE), Saks Fifth Avenue shirt (similar HERE), Briefcase c/o Maxwell Scott (similar HERE), Timex watch, Nordstrom pocket square, To Boot New York shoes (more affordable HERE) | PHOTOGRAPHY | by Rob McIver Photo

Briefcase - He Spoke Style

Thanks for reading.

Stylishly Yours,

He Spoke Style


Chime In

  • Jay Goodwin


    I’ve been dying to learn how to tie that knot you’re wearing. I know the 4 standard knots, but can you give me the name of the knot your wearing. I love how the knot is double-layered.



    • Brian Sacawa

      Wow, lots of interest in this tie knot! It’s a double four-in-hand. Tie it just like the classic four-in-hand, except wrap it around twice before pulling the long end through. A little trick is to keep your index finger underneath the first wrap-around so it’s easier to pull through and keep the second wrap around close to the first. Coincidentally, this is on my short list for an upcoming series of “how to” videos. Cheers, Jay.

  • Jonathan

    I would also like to know how you make tha knot, Ilove your style.


  • Colin

    me too – your tie knot