Best Bet: Paris Fifties Dress

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Photo: Courtesy of asos.com

This demure dress by River Island offers an understated dose of fifties flair. The A-line silhouette makes it suitable for the office paired with a cropped blazer or cardigan, while the keyhole cutout and bold pattern stand out at happy hour. Though the defined waist and flared skirt evoke a bit of Mad Men style, the punchy abstract print keeps the dress from looking dated. Wear it with black tights and heels in the winter, then pair it with wedges when spring (someday, eventually) returns.

River Island Paris fifties dress, $77.56 at asos.com.