Leather Duffle Bags & Weekenders: A Guide


by Dave Johnson 

Rhett McLaughlin from Rhett & Link once said, “Right now I’m thinking about the people who invented words. Did they just look at stuff and say the first thing that came to their minds? If so, how do you explain ‘duffle bag’?” Such a thoughtful guy. Well, Rhett, let’s talk about that.

Every year around spring time, I get the itch to go on a road trip. Because of the duration of the trip, I don’t need to take a giant suitcase with two weeks’ worth of clothes. I just need to take three days’ worth—max. Enter the duffle bag and the weekender.

Jackson Wayne leather duffle bag in saddle tan

A Brief History of the Duffel Bag

The duffle bag originated in Duffel, Belgium in the 17thcentury, where the canvas bags became popular with sailors. Fast-forward a few hundred years, and they were issued to soldiers in World War II. And like many things in post-war America, the duffle bag was popularized by former soldiers after the war ended. Today, duffle (or “duffel”) bags are usually cylindrical bags made from cloth or leather, with a long, zippered closure on the top—sort of a soft-shelled suitcase. And, yeah, they’re usually pretty cheap.


What is a Weekender Bag Anyway?

The weekender is a bit different. It doesn’t have a history that is as clear-cut as the duffle, but it’s thought to be an answer to the rise of business travel in the last fifty years—particularly with men who wanted a masculine bag option. It certainly takes some aesthetic cues from the duffle, but is a modified, smaller, more fashionable version, that is ideal for those weekend road trips or as a carryon for flights. Though duffles are made with either leather or cloth, it’s far more common to find high-end weekenders made of leather or mixture of leather and cloth.

With all that said, there are no set rules or guidelines on the sizes of these, and you will find a lot of variance with both. But generally, duffle bags are larger, and weekenders are smaller and more portable, able to hold enough clothes for a weekend. You’d be surprised how much these can hold, too. Duffles can hold an insane amount of clothing—especially if you pack wisely. Weekenders can hold a lot too. I’ve fit a dopp kit, 3-4 changes of clothes, a jacket, and shoes in my weekender, and still had room to spare.

Airline Compliant Duffle Bags & Weekenders

I think duffles and weekenders are particularly great for flights, duffles being better for checked bags, and weekenders better as carry-ons. If you’re flying, it’s important to know if your weekender is small enough to take on a plane in the first place. The size restrictions vary from airline to airline, but generally the size is roughly about 22 inches x 15 inches x 10 inches, give or take an inch or two. I’ve found that most airlines aren’t too strict with the sizes, so if it looks like it’s the right dimensions, you probably won’t get much fuss over it. Of course, that’s all subject to change.

A Few Suggestions for Duffles & Weekenders

I’d be remiss if I didn’t recommend a couple of great Jackson Wayne options for your duffle bag or weekender needs. And this is where I get really excited about the topic, because I think Jackson Wayne not only has a great duffle and weekender, I think they have the greatest ones on the market right now.

Firstly, both the Duffle and the Weekender from Jackson Wayne are very similar in design, taking aesthetic cues from bags from the 1930s and 1940s. They both have great features such as: comfortable double-layered carrying handles, padded shoulder straps, solid brass hardware and zippers with convenient pull tabs, and outside and inside pockets that easily accommodate your phones, chargers, and boarding passes (I can fit an iPad mini in the inside pocket). Of course, they both have very high-quality components like full-grain, vegetable tanned leather, and heavy gauge thread. And they both have the same dimensions, making them land comfortably within airline compliance for carry-ons. The biggest difference between the two is that the Duffle is all-leather, and the Weekender is a mixture of leather and waxed canvas. (More on leather vs. waxed canvas here.)

So let me give you my thoughts and experience with these bags. I love them. I recently got one of these and just fell in love with its great design. I’ve spent time with a lot great leather bags, many of them very expensive and well-known. But I can easily say that these are the best I’ve ever seen. They offer a lot of utility, the design is perfect, the quality is sublime, and the value is off the charts.

The all-leather Duffle Bag is really something to behold. If you are looking for that perfect leather bag for travel, I really think Jackson Wayne has perfected it here. They took a lot of time intentionally designing these bags, even down to the thickness of the leather, which is slightly thinner so it’s not too heavy, but is still very strong. Also, the inside is lined—which is a premium feature by itself—but it’s lined with canvas, so it won’t rip like so many other chintzy linings out there.

And the Weekender is no slouch either. Sometimes canvas or waxed canvas bags can seem like the black sheep of the leather bag world, but not so here. Jackson Wayne uses a beefy waxed canvas that is superb. I love how light it is, while still feeling substantial and strong. I really like that it feels like an expensive “army” bag, and it oozes classic masculine vibes. And the best part of this bag to me, is that when you aren’t using it, it flattens easily, making it easy to store. It doesn’t hurt that it’s lighter and cheaper than the leather option, too.

These bags are perfect. Not too big, not too small, and every feature is exactly what you want and need. Not all weekenders and duffles are like that, but these certainly are. And whatever bags you decide to buy, just buy quality.