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The Classic Weekender

The Classic Weekender

Regular price $139.00
Regular price $199.00 Sale price $139.00
Sale Sold out
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The perfect bag for short getaways, commutes, the gym or overnight stays, offering ample space to carry essentials without the extra bulk. Its compact size and full-grain leather design make it easy to carry and store, effortlessly fitting into overheads, lockers, trunks or under seats. Its versatility and unmatched style will make it your go-to bag for all occasions. Now you can make a statement where ever you go, with a gorgeous, easy-to-clean bag built for your on-the-go lifestyle.


  • Bag Size: 19” (23.5L)
  • Strap Length: 38"
  • Handle Drop Length: 12"
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Absolutely love my bag!

Absolutely love my bag! It is the perfect size for weekend getaways and fits all my personal items. The quality, size, and color of the bag is great to use casually or for work tips. The bag came quickly after placing the order and was beyond what I expected. Very satisfied with my purchase.

-L.f. (June 3rd, 2022)


Click below to discover what makes our bag head and shoulders above the competition



STRESS-FREE TRAVEL - our just-right sized bag (19”, 23.5 L) allows you to effortlessly get from A to B with your essentials - clothes, toiletries, electronics & more

PROTECTED FOR YEARS - Our bag has an inner liner to protect the leather from the contents within the bag and regular wear and tear.

LOOK YOUR BEST - our full-grain, handmade and buttery-soft leather bag with our accented liner uplifts your look with true class

QUICK ACCESS ON THE GO - our outside pocket and well-constructed zipper allows you access the things you need when you need them.

CARRY WITH COMFORT - our bag's proprietary U-straps allow you to wear as a backpack or over your shoulder


An amazing story from an experienced customer

Many years ago I used to design a private-label brand of bags for the Scuba industry and it made me a bit of a bag snob. There are features that I always look for in a quality bag, and it's surprising how many skip those features.

#1 - for me - do the straps wrap around the entire bag, and NOT split at the bottom seam? This bag goes beyond that. Each strap forms a "U", with the handle being at the bottom of the "U" - so it won't split. On the bottom, the straps extend past the bottom seam in both directions and overlap by almost 3". The strap is folded over and sewn on all four sides, plus in an "X" across the middle. Why is this important? The weight and stress is on the straps - not the bag. That means the bag will last a LOT longer.

Next are the edges, seams and ends. Are they bare, sealed, rolled, etc? Every seam and edge is rolled - not just sealed.

Zippers. Do they simply end at the bag ends, or are there end tabs for stress relief? This has end tabs. That extends zipper life and prevents damage to the zipper and bag...

It's a beautiful bag in both looks and quality and I expect it to last a lifetime.

-Richard C. Drew


30-DAY MONEY BACK GUARANTEE - Every bag comes with a money-back guarantee and free shipping.

CRUELTY FREE – Our leather is processed at one of the most eco-friendly tanneries on the African continent. We only use products that come from grass fed free-range animals that have been treated in the most natural way.

CELEBRATING CULTURE AND ARTISTS - All JW Brewster products come with a flier giving a brief description of the bag's artist so our customers can celebrate their bag’s heritage with us. We love supporting minority communities and are LGBTQA+ owned.

Note: The classic model has all the quality and most of the features of the luxury bag. A little less leather and no removable liner but a lot less price! The Classic JW Brewster does not have leather accents on the shoulder strap, U handles, or piping along seams. The Classic also has a permanent liner vs the removable liner of the Luxury bag. If you're interested in these features, please click here to checkout our Luxury Weekender.

Customer Reviews

Based on 12 reviews

This bag has turned weekend trips into a breeze. It’s the perfect size for any short trips that you don’t want to bring a larger bag or suitcase for. I expected a weekender (smaller) sized duffle and that’s what I got. The leather is great quality and still looks perfect after much use. Overall love how the bag looks!!

Great gift

I gifted a “classic weekender” bag to my father-in-law. I’ve heard him chat about how the leather was sourced and assembled in Africa by villagers who earn a living wage. I’ve seen him use the bag on 3 different trips since Christmas (6 months).

Daily use bag

This bag is perfect for a quick run to the gym. The straps are just the right length to throw over your shoulder and go. The zipper opens and closes smoothly no mater how much I stuff in the bag. The outside pocket is perfect for my phone and keys.

New favorite bag!

Awesome quality bag! The sustainable manufacturing is an added bonus!

Quality Travel Bag

Love the way this bag looks and feels - it's a simple, classic design with accents that make it pop! The perfect size for a few outfits and a pair of shoes. Well-made and durable as well as stylish, and all at a reasonable price point!