Back in 2014, Waterfield made a messenger bag called the “Rough Rider“. It was expensive, around $350, so I put off buying it. I figured I’d save a little a purchase one later. That time never came and Waterfield stopped making them and the “Maverick” took it’s place.

The Maverick is a nice bag but I prefer the stylings and design of the Rough Rider so every now-and-again, I find myself searching eBay to see if I can find one that someone is looking to sell. I never do.

The last bag I bought was made by Fossil called the “Troop East/West Messenger”. It’s canvas bag and it has served me well for the past 8-years but I do wish it had a bit more structure to it. Looking at it sitting by my desk right now, I realize I am quite fond of it and how well it’s held up.

That being said, I do lament that I didn’t jump when I had the chance.