Photographed by Annie Leibovitz, Vogue, September 2017

I am not a jean jacket person. I’d rather feel perpetually chilly and covered with goosebumps than throw one on over a dress on a brisk spring day. Sure, jean jackets are supposed to be a closet staple, an easy throw-on, something to add cute embroidery to and gift because they’re so low-risk. But these seemingly humble jackets have drawbacks for me.

“Just try it on!” a friend will say, handing me her jean jacket. She thinks that when I said “jean jackets don’t look good on me,” it meant I am still on the hunt for a classic jean jacket, and maybe hers is the one I’ve been looking for all along. I am not, and it is not. But I try it on anyway, to avoid further pestering. Then she does what she’s always done — cocks her head and squints at the grand reveal, and maybe even places her fist under her chin, searching for an angle that makes me look good before giving up. “I told you,” the big, ugly, boxy thing formerly known as Rachel Besser says to her, slipping the jacket off, shapeshifting back into myself.

I’m smaller on top and larger on the bottom, kind of like a pear, so the classic boxy iteration of the jean jacket doesn’t flatter my form. Yet contemporary designers are trying to turn people like me into converts by dreaming up new denim silhouettes that feel more tailored (read: cinched at the waist) while maintaining the jacket’s youthful appeal. The squarish silhouette that was first worn by miners and cowboys of the Gold Rush is now showing up in belted denim trench coats, shackets (the child of a jacket and a shirt) made with less rigid fabric, and smart blazers. Will I ever wear a classic jean jacket? Probably not. But denim vests and longline coats make me think a denim topper might be for me, after all.

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