• Meet the Roll-Top Pack

    Winter Session Waxed Canvas Roll Top Pack
    In the process of making any new Winter Session product, we always try to strike a balance between function, versatility, and style -- and the Roll-Top Pack is no different. 
  • Meet the Day Bag

    As we continue to expand our collection of quality products, we are always looking to improve upon our classic designs and to satisfy the diverse needs of our customers. This is how the Day Bag came about: we wanted to make a bag that can conveniently carry daily work and travel necessities, but that also closes securely with a zipper.

  • Meet the Leather Garrison

    Ladies and gentlemen, for the first time in Winter Session history, we’ve done it! We’ve finally created an all leather bag for you to enjoy.

    Our new Leather Garrison takes on the form and silhouette of the classic Garrison, but instead of canvas we’ve chosen three variations of cowhide for the bag body. Our Natural tote is cut from soft, undyed vegetable-tanned cowhide from the Hermann Oak Tannery, while our Black and Cognac totes are crafted using the renowned Horween Leather Co’s Essex leather -- a vegetable tanned, oil-infused leather with a very supple feel that will age beautifully. The handles on all three totes are cut from thicker vegetable-tanned cowhide (also from Hermann Oak). We’ve chosen each of these leathers for their unique structural and aesthetic characteristics and their superb quality.

  • Meet the Zip-Top Tote

    Introducing the Zip-Top Tote: our take on the classic, over-the-shoulder carry-all. Its simple, pared down design, zipper closure, and lightweight single-layer construction make it the perfect companion for weekend travel or daily use.

    We’ve constructed the body of the Zip-Top Tote using our signature 20 oz heavyweight waxed canvas, which will withstand the change of seasons and wear beautifully over time. Popping up from the rim of the bag, a flexible zipper panel (made from a contrasting lightweight 10 oz canvas) provides both easy access and extra security. Detailed with a solid brass YKK zipper, the pop-up panel allows you to fill the bag to the brim for greater carrying capacity.

  • Meet the Garrison

    Our goal has always been to create beautiful and useful pieces that become companions for life. Each season we are able to focus and streamline our design process a little more as we continue to refine each of our pieces for optimal, seamless use. There is no Winter Session bag more iconic and functional than the Garrison Bag; it's one of our first and most lasting designs.

    After receiving valuable customer feedback over the past year, we have opted to replace the Large and Small sized Garrisons that we offered last season with a nicely balanced proportion that feels 'just right'. The updated Garrison Bag -- sized squarely between the Large and Small -- is the perfect size for any occasion, whether you’re commuting to work, ducking outside for a picnic, or taking a weekend road trip. Staying true to its original concept, the new Garrison functions like a well-organized catch-all for your daily necessities. Slip in a laptop or iPad, charger, and a large notebook on a more productive afternoon; pack a camera and a few extra layers for a day of exploring a new place; or fill it with a loaf of bread and other treats from the market for a cozy evening with friends.

  • Meet the Felix Bag

    The Felix was an early Winter Session design that had drifted to the archives as we focused on developing other styles. But thanks to popular request, in 2014 we decided to reintroduce it into our collection. After improving and refining design details, we’re pleased to share the new Felix Bag with you.

  • Meet the Day Pack

    All of our bags are designed with flexible functionality in mind, but our Day Pack is arguably the most adventure-friendly. Inspired by the sleek style of streetwear rather than the bells-and-whistles of a trail rucksack, we’ve found it to be equally adaptable for a Saturday in the city or stashing a day’s supply of snacks on the trail. Let’s take a tour of the Day Pack!