How to style a jean jacket has always been a matter of reinvention. A blue denim jacket is one of those rare wardrobe staples that never fully disappears from the trend cycle—it just evolves.

Take the humble denim jacket as a prime example: Introduced by the one and only Levi Strauss in the 1880s, the silhouette can go from midday errands to a laid-back date night in one fell swoop.