October’s best streetwear drops came in a rush. Supreme and Timberland marked 20 years of working together, Stüssy and Denim Tears reunited for fall, Kith opened a new flagship and released its latest chapter with Giorgio Armani, and Kith and Salomon are up next. Here is the rundown.

Supreme x Timberland, 20 years in

Supreme and Timberland first collaborated in 2006, and their fall 2026 collection dropped Oct 22 at 11 AM ET on supreme.com and in Supreme’s stores, with Asia following on Oct 24. This one is all apparel, no boots. Sole Retriever, HNHH and Sneaker Bar Detroit list:

  • A suede puffer jacket in wheat, salmon pink and black, with a faux-fur hood and the Timberland tree on the back
  • A Ventile utility jacket in olive, salmon pink and black, made from waterproof cotton with a Polartec 200 lining
  • A Polartec jacket in a navy print, with a matching balaclava
  • Long-sleeve football tops, thermal-lined zip hoodies, denim utility pants and knit beanies

The wheat suede puffer is the piece that best captures what made the pairing work in the first place: Timberland’s workwear colors on a Supreme silhouette.

Stüssy Tears returns

Stüssy and Tremaine Emory’s Denim Tears reunited for fall/winter 2026, releasing Oct 16 at 11 AM ET on stussy.com and denimtears.com, at select Stüssy Chapter stores, and at Denim Tears’ flagships at 176 Spring St. in New York and Lenox Square in Atlanta, per Hypebeast. The standout is an orange technical windbreaker that frames Stüssy’s double-S with Denim Tears’ cotton wreath, alongside co-branded jackets with an “S” emblem across the back, Pause reports. It is the latest chapter in a partnership that goes back to 2022.

Giorgio Armani x Kith, chapter three

The third chapter of Kith’s partnership with Giorgio Armani, “Dreams of the Dune,” launched Oct 16 at all Kith stores and select Armani stores. Shot in Marrakech’s Agafay Desert, it leans into leather and shearling: a belted shearling jacket, a two-tone lamb leather utility jacket and a lambskin suede blouson, with partner capsules from ASICS, Diemme and ’47, Galerie reports.

Kith opens in Vancouver

Kith now has a second Canadian flagship, in Oakridge Park’s North Arcade on West 41st Avenue in Vancouver. Ronnie Fieg designed it with Porto Architecture in walnut, Calacatta Vagli marble and Belvedere stone, and it includes Kith Kids and Kith Treats, per Hypebeast.

Up next: Kith x Salomon, Oct 26

Kith and Salomon’s Winter 2026 collection, which hit the Vancouver store first, goes global Monday, Oct 26, at 11 AM local time on Kith.com, the Kith app and in Kith stores. Sole Retriever and JustFreshKicks list three pairs:

  • XT-4K Mid, a new model, in Black/Green Gaze-Olive Night
  • XT-VYGR 2 in Dark Navy/Dusty Orchid-Transparent
  • XT-4 OG, a Kith exclusive, in Maroon Banner/Nocturne-Knockout Pink

Prices hadn’t been announced at the time of writing. Sole Retriever reports that the app raffle closes Oct 25 at 11:59 PM.

In case you missed it

Palace opened its Winter 2026 season on Oct 2 with a first drop headlined by a 2000 AD “Judge Dredd” capsule, a GORE-TEX parka and Realtree camo, per Hypebeast.