Bespoke Post: The Weekender Bag

The holidays are upon us. Good food, good company, and (typically) lots and lots of travel. Whether you’re flying or driving, it can be a tough decision on what to bring and, just as importantly, what to bring it in. While, I won’t look down on anybody lugging a brightly colored wheelie suitcase or a backpack on a plane, it just doesn’t feel right when I do it.

In comes the need for a stylish, compact bag for carry on, or for weekend road trips to…well, pretty much wherever. While there are many options for this type of bag out there, I happened upon this guy from a company called Bespoke Post.


This bag is made out of a tough canvas material and is based off of the tool bags that stonemasons used to carry around their tools in. It has a reinforced frame that keeps it from losing it’s shape, and helps with being knocked around while you’re on the move. The handle and accents are leather, which lends it a look of sophistication that a backpack or duffel bag is missing, and the clasps and rivets are all super solid.


My main concern when I got this bag was space. When Cassey and I take weekend trips, we typically bring a couple of changes of clothes each, but don’t like to bring more than a bag or two.

We were able to comfortably fit multiple outfits in there, shoes included, as well as other essentials, such as toiletries, electronics’ chargers, and a good book. As a further test, I took this bag to carry my uniform to work one day and it comfortably fit my 9 inch steel toe boots, a pair of my NWU’s, undershirt, fresh socks, and my shaving gear, with room to spare. No small task as anybody in the military could tell you.

And despite the hauling capacity, it stills works very well as a carry on. I hate checking luggage if I don’t have to.


As I said earlier, there are a TON of options for men’s overnight bags (see my other favorite picks at the end of the post), you can’t go wrong with Bespoke Post’s take on it. It’s small enough and versatile enough for a weekend road trip or a holiday flight home to see family, yet still durable enough to take a knocking around in transit. I haven’t been able to find bag this handsome at a price near where this guy is yet, and I’ve been looking.


For those interested in this specific bag, Bespoke Post is a monthly subscription box club that is free to join and has some really great boxes that you can choose from each month for $45 a box. And if a month roles around and you don’t see anything you like, or you don’t want a box that month for any reason, you can opt out for free.

The quality of the items in boxes are fantastic, the items I receive would typically cost $80-100 for something of similar quality from another company. In addition, you can utilize their store to throw in some add-ons to your box (it’ll ship free at the same time as the box), just to enhance the purchase.

If you want to try out Bespoke, feel free to use my referral link.


other great bags

The Air Boss by Red Oxx | The Mayfair Duffle by Fossil | Medium Duffle by Filson

what i’m wearing

shirt J. Crew | pants H&M | watch Daniel Wellington