Engineered Garments Short Coverall Denim Jacket
Credit: Photograph by Michael Pirrocco

If you're bored with the classic denim jacket silhouette and want something more versatile, look no further than Engineered Garments' Short Coverall Denim Jacket. With over-sized pockets and detachable hood that buttons up around the chin, its shape is similar to a hoodie or a windbreaker. Bright white contrast stitching and thick drawstrings around the neck make it the preppiest jacket on the list. [$435; barneys.com]