Drake Cross Body Bag
Drake Cross Body Bag
Drake Cross Body Bag
Drake Cross Body Bag
Drake Cross Body Bag
Drake Cross Body Bag
Drake Cross Body Bag
Drake Cross Body Bag
Drake Cross Body Bag
Drake Cross Body Bag

Drake Cross Body Bag

Regular price $159.95 Sale price$149.95
Tax included.

  • 16oz Waxed Canvas
  • Solid Brass Hardware
  • Lifetime Warranty
  • Ships in 48 Hours (Ex Pre-Order)


Introducing the Drake: not just any side bag, but a testament to timeless craftsmanship. For the man (or lady) who values authentic, old-school charm, this bag boasts heavy 16oz waxed cotton canvas, ensuring both water resistance and a one-of-a-kind patina. Adorned with genuine brass hardware that ages gracefully and eco-friendly vegetable tanned leather that outlives its contemporaries.

But the Drake isn’t just about aesthetics. A full-length weather flap ensures your essentials remain shielded, while the clever glasses loop keeps those shades in check. Carry by hand or swing across the shoulder, all while enjoying our Ironclad Lifetime Warranty. Compact, yet with ample pockets, the Drake stands ready to make each day a journey in style. After all, if you think this is an ordinary bag, you don't know Jack.


  • Australian Designed
  • Solid Brass Hardware
  • 16oz Beeswaxed Cotton Canvas
  • Water Resistant but Breathable
  • YKK Tough Woven-in Zippers
  • 100% Vegetable Tanned Leather
  • S40 Luggage Strap Included
  • 16cm L, 22cm H, 6cm W
  • Magnetic Closing Studs on the Front Flap
  • Hand Carry Loops on the Back
  • 4 Zippered Pocket Compartments

Old-School Craft for New Age Adventurers

Waxed Twill

Traditional cotton twill that has been wax treated to repel water. Unlike manmade fibres such as nylon and polyester, waxed cotton breathes and ages with a leather-like patina.

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Real Brass Hardware

Genuine solid brass hardware is rarely used because it's expensive. We say- hang the expense! Real brass is heavier than the fake alternatives and develops an authentic patina.

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Eco Leather

Otherwise known as Vegetable Tanned Leather. It's genuine cow leather that is processed using traditional methods. It's more expensive and requires more time but it lasts up to 4 times longer.

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Lifetime Warranty

We stand by our heritage craftsmanship. Built to last a lifetime and age gracefully; your trust is our promise. You invest in us, we invest in forever.

Hassle Free Returns

Shop confidently with Jack Stillman. Easy 15-day returns, no fuss. Because quality matters, and your satisfaction is our promise.

Over 20k Since 2014

Crafting heritage since 2014: 20,000 customers, 20,000 stories, and counting!

Australian Owned

Authentically Australian-owned and operated. Crafting heritage bags and accessories with old-school materials, we honour our roots and embrace tradition.


Waxing canvas is a natural way or protecting the fabric and whoever is under it. The wax finish causes water to bead off instead of soaking into the fibres. The advantage is that this method of proofing the fabric also allows it to breathe, unlike the plastic treatment options found in waterproof fabrics. Want to know more? Read this article.

Yes. This product is covered with our lifetime guarantee. That means we are super confident that our manufacturing process is so tight won't see a popped seam or a shonky zipper anytime soon. We aren't saying the product is indestructible, but it certainly is built to last. Read this article for more information on our Warranty.

Waxed canvas is easy to take care of. The ensure the longevity of the canvas we recommend you re-wax it at least every 12 months. This keeps the product water-resistant, mould resistant and it also binds the fibres together.

We know you want your stuff ASAP. If your order is not a pre-order please take note of the following. 

  • We try to ship orders within a 48 hour period after receiving your order.
  • We ship using Australia Post from Perth Western Australia. That means items shipped to the Eastern States of Australia can take between 6-14 business days. If you are not sure, please chat with us. 
  • We ship worldwide but overseas delivery times can vary from country to country. 
  • Free Shipping is offered for orders over $200 within Australia.
  • If your order is for a pre-order, we will contact you with updates as the order progresses.
  • All orders will receive a confirmation email once the order is made and another when the order is shipped. If you don't receive these please contact us. 

Since 2018, we have made Jack Stillman products in-house in our Australian owned and operated facility in Vietnam. It is because of this that we can confidently offer our lifetime guarantee. To learn more about our manufacturing, read this.