UGG and JW Anderson have fun with tradition for fall 2026, turning the respectable penny loafer into something delightfully oversized. Jonathan Anderson applies the classic shoe’s signature strap and stitching to UGG’s familiar Tasman and Classic Boot, creating two shearling-lined hybrids with exaggerated rounded toes and chunky proportions.
The $300 Loafer is particularly cheeky, resembling a penny loafer inflated to cartoonish dimensions, while the $400 Loafer Boot extends the story up the ankle. Available in Chestnut, Khaki, and Orange, the designs reflect Anderson’s longstanding fascination with transforming everyday objects with unexpected proportions.
Musician Dev Hynes fronts the accompanying campaign, photographed by Zhenya and Tanya Posternak and styled by Anderson himself. Wearing the shoes with everything from rolled-up jeans and colorful knitwear to roomy black tailoring, Hynes demonstrates how comfortably the absurd can fit into an everyday wardrobe. The collaboration launches October 15, 2026.
UGG x JW Anderson
UGG recently unveiled a social-first campaign featuring Orville Peck and its Western collection.
Dev Hynes slips into a plaid shirt and jeans for the UGG x JW Anderson campaign. An Anderson statement, the uniform also made an appearance in Louis Vuitton’s recent advertisement with Drew Starkey.
