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]
Credit: Photograph by Michael Pirrocco
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