Rag & Bone - Deerhide Café Racer Leather Jacket $500 ($325 with additional discounts)

This is actually an insane deal for a jacket that will last you 10+ years. Deerskin is unique because it has the toughness and durability of cowhide but the softness and pliability of lambskin. Sign up for the 20% discount for $100 off. Stacks with AMEX $75 credit after spending $275+. On top of that, Rakuten gives 2.5% cashback. Final sale so check your size.