A military staple since 1917, when the U.S. Army issued leather flight gear to its pilots, the bomber jacket—with its requisite knit trim at the cuffs and waist—has undulated in and out of fashion ever since, making its last big style splash back in the ’80s. But 2014’s version isn’t The Fresh Prince of Bel-Air’s bomber: Today’s model has an updated look and comes with new ground rules.
“A bomber jacket should hit right above the hips and be more fitted and less boxy than the ’80s version—which is great, because it accentuates your shoulders and makes your legs look longer,” says Kevin Harter, Bloomingdale’s VP of Fashion Direction. “My favorite style is a more luxurious bomber worn with a simple tee,” he adds. “And for a late-summer slash-early-fall look, combine it with a fitted fleece sweatshirt and some tailored shorts. You can also pair it with a great knit shirt, some fitted fleece bottoms, and a pair of cool sneakers, or—to dress it up—a shirt and knit tie.”
But resist the urge to push up the sleeves, Harter says: “That isn’t the look I’d go for—to me, that seems very ’80s!”