You can't get much more classic and cool than a Baracuta G9 jacket. Made famous by Steve McQueen in The Thomas Crown Affair and James Dean in Rebel Without A Cause, the windbreaker style zip-up got a fresh update thanks to some premium leather replacing the usual water repellent outer shell. There are three variations of the updated G9, each with a slightly different look. It's hard to go wrong with any choice.
Pair one of these with practically any look this autumn and winter and you'll constantly feel like the sharpest guy in whatever room you're in. H/T to Selectism for the heads up.