There are some people whose wardrobes you admire from afar, and then there are those whose essence you want to embody. Alexa Chung, whose self-assured style strikes the delicate balance of aspiration and approachability, has always been the latter. Her own wardrobe (and well-documented love of vintage) is an enduring source of inspiration—and overarchingly what informs her third collection for Madewell, out on November 10.

The 31-piece capsule, additionally, borrows from some of New York’s most storied characters: There’s a nod to Fran Leibowitz’s masculine tailoring with jeans, a hat tip to Patti Smith’s borrowed-from-the-boys attitude, a hint of Debbie Harry’s ’80s glam. “So many of my style icons have quite tomboyish style,” Chung shares, “but as I’ve got older, my taste has evol…

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