Finding Stylish Weekender Luggage

June 11, 2018

There’s something wonderful about weekender luggage. You’ll never use them often — unless your life is fancier than mine — but when you get to break them out, they add to the pleasure of being able to get away for a short trip. Suitcases are too spacious, too bulky. When you have that much room, you’re overeager about packing. You end up bringing too much stuff, killing the pleasure of being able to get away from distractions. Like fat paperbacks and quick taxi rides, weekenders make getting away actually feel like getting away.

The weather has been warming up in California and I’ve been using the opportunity to take short trips. Packing for a two- or three-day getaway is easy since you know exactly what you’ll be doing — there aren’t any surprises, so you know if you’ll only need to wear jeans or have to pack some dressier trousers. You only need one jacket, which you can wear; then a sweater that can be packed. Throw in some underwear and shirts, and everything can fit into a weekender bag.

Some things I’ve found to be important when shopping for the right weekender:

  • Consider the Weight: The internet is full of images of celebrities carrying their weekenders by hand, all the while looking stylish and glamorous. Don’t be fooled — these people have limo drivers and porters to help them along the way. You, a non-celebrity, will likely have to carry your weekender by hand the entire time, so be conscious of the bag’s weight. If the bag is too heavy to begin with, even a light sweater and ham sandwich inside can make you feel like you’re carrying the world after a while.
  • Decide on the Material: Leather weekenders can be tremendously handsome, but they’re typically heavier than bags made from cotton or nylon. That said, if you know you’ll mostly be taking car trips, where you’ll only be lugging this from your trunk to the hotel, they can be a great options. Canvas and nylon bags, on the other hand, are lighter and often more casual, depending on the design. And they’re easier to clean.
  • Think About Alternative Uses: Few of us will take more than a couple of weekend trips per year, so consider alternative uses. I use a leather weekender as my carry-on luggage for longer flights. My arms are saved by the fact that the bag can be set on top of my roller luggage, so I rarely have to bear the weight. If you plan on using a weekender the same way, check your airline regarding restrictions (different airlines have different regulations regarding carry-on size). A smaller bag made from cotton or nylon, on the other hand, can be used for the gym — and you can throw it in the wash if it starts to stink.



Standout Weekenders

There are a ton of options on the market for good weekenders, but I think some are standouts. Two of them are at Bennett Winch, a British manufacturer of high-end cotton canvas bags designed with a classic, but contemporary feel. These look clean enough to be used with sport coats and suits, but also have a vague militaristic vibe to go with most casualwear. They use a sturdy, brushed cotton canvas that’s water resistant, as well as brass hardware and vegetable-tanned, full-grain leather for their trims.

The company’s signature bag is their weekender, which is designed with a padded laptop sleeve and separate pockets to hold shoes (keeping those dirty soles away from the rest of your clothes). They also recently designed a suit carrier holdall, pictured above, with Simon Crompton from Permanent Style. Here, a garment bag wraps around the central, cylindrical shaped carryall, with magnetic bits keeping everything in place. You can read more about it at Permanent Style. Unlike some bags, which try to do too much, this seems simple enough to use while adding some thoughtful functionality. They are, however, expensive.

For something more affordable, check Rapha. Like Bennett Winch’s weekender, this has a padded laptop sleeve and separate compartments for footwear. There are two slip pockets on the outside that give you easy access to important items, while the main pocket folds down so you can see and access all of your kit. It’s made from nylon, not finer cotton like Bennett Winch’s bags, but has a sportier feel that could look great with decidedly casual wardrobes. Also attainable at $235.

Lastly, Frank Clegg Leatherworks has a line of travel luggage in different sizes. I bought their Signature Travel Duffle last year in black tumbled grain leather, which is what I’ve been using on my trips. The bag doesn’t have any fancy features, but it’s beautifully made by Frank and his sons in Massachusetts. The design is simple and classic, with a spacious interior that allows you to organize your items however you want. Since they smartly designed the zipper to extend past the bag’s opening, you can open the bag a bit more easily and fully in order to dig around for your contents. This is the sort of bag you can keep for decades. And while it’s made from a sturdy, full-grain leather, I find it’s no heavier than some of my briefcases. The Armoury also co-designed a garment bag with Frank Clegg, which you could use to supplement with their luggage.



Other Notable Options

There are some great European companies for leather weekenders, such as Luca Faloni and Troubadour, which feel sophisticated enough to use with tailored clothing or more refined forms of casualwear. Enrile’s luggage has a classic French look, like something you’d expect to see at Hermes. In the US, I like Stoffa (pictured above), who uses a lightweight calfskin backed with a polymer to give the bag structure. It’s a smart way to get the look of a leather carryall without any of the weight. Alternatively, San Francisco’s Glaser has a line of handsome travel luggage with various built-in compartments (as well as accessories you can use to organize your stuff within the bag). Should none of the ready-made designs suit you, they can also design something from scratch (see their bespoke service).  Brooks Brothers and Ralph Lauren can also be good, but just be careful of the quality — some are wonderful; others less so.

For cotton carryalls and weekenders, check Orvis, Filson, and JW Hulme if you want something with a rugged American feel, then Paravel and La Portegna for something refined. Chapman has a line of sporty, British-made holdalls in various shapes, while our very own Jesse has raved about how much he likes Beckel (he gifted one of Beckel’s duffles to his brother-in-law). J. Crew’s duffle bags can also be had for under $100 on sale. And finally, if you’re ok with nylon, it would be hard to beat Briggs & Riley. Their simple, lifetime guarantee covers all of their luggage, such that you can get anything repaired, even if you don’t have the original receipt. It’s a policy that’s raved about on airline forums, and will keep you from worrying about whether you’ve wasted your money on something that will break down.


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