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If Serena Williams stepped into a scene from Sabrina.
Borrowed from the boys and worn a little oversized with skinny pants, it'll read like super-expensive Altuzarra.

A tomboy, Chloe Sevigny-like spin on the country club staple.

Maria Sharapova wears a version of it, like, every day. (VPL for Nike, perhaps? Fingers crossed.)

Fanny packs might never make a comeback, but even Marc Jacobs likes a good visor.

Toughen it up with a leather jacket and bedhead to steer it from mixed doubles to mixed drinks.

Solves the problem of what to wear with fall's novelty sweaters and velvet loafers on still sorta-summery days.

Needs an equally kitschy doubles partner, like a bird print blouse or librarian glasses.
The best way to top a pencil skirt and heels. (And to get your letter jacket when you really only made the thirds team in high school. Whatever.)
The kind of Narciso Rodriguez-y number Gwyneth would throw on to host a last-minute summer dinner party. (On her tennis court, maybe.)
With motorcycle boots and morning-after eyeliner, it's less suburban mom and more subversive art student.
Unlike the Isabel Marant high-tops, you can actually work out in them, too.
Just add a fuchsia lip (and maybe a really good bronzer).
It's okay to let your gym bag upstage your handbag.

To avoid the early '00s bohemian look, pair it with crisp pants and button-downs instead of maxi dresses.

Alexa Chung-ify your floral sundresses.
Only Alex Wang could make a solid-colored, calf-length sheath look more badass than corporate.