Denim jackets are all the rage these days, and while a classic trucker jacket can't be beat, Gap's understated 1969 line offers a slightly dressier take on the rugged staple. This denim blazer has a notched collar and a relaxed 3/2 roll button stance, casual patch pockets and a single back vent. Get tonal by pairing it with a pair of washed denim, or even white jeans. Just remember the golden rule of wearing denim-on-denim: make sure that one of the pieces is noticeably darker than the other.
$79.99 / $59.99 ($51 with code), by Gap