Reese Witherspoon ditched her usually classic ensembles for something a bit more multifaceted, and I'm proud of her for expanding her horizons. While out and about with boyfriend Jake, the actress wore an airy black jersey dress, a cropped red cardigan, and accessorized with studded Tod's sandals and a woven Bottega bag. It seems more and more actresses are bringing the fedora back. Since it took a long, much-needed break, a comeback was in order.

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