BERETS REPRESENT three things I’ve always aspired to be: French, chic and confident. The first is a lost cause, given my Italian heritage and American upbringing. I’m working on the latter two. I’ve worn berets with varying degrees of success since childhood and sported a black iteration with a crystal-encrusted band to dine with my father just last month. He told me I looked “very French”—a high compliment coming from a man who proposed to his wife in the City of Lights.

Twiggy, the lanky model who defined the look of swinging...