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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.

1.) Baracuta G9 Shearling-Sheep Skin ($1,669)

2.) Baracuta G9 Dark Brown Classic Leather Jacket ($1,063)

3.) Baracuta G9 Classic Vintage Leather Jacket ($1,063)

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.