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Crawford paired the look with feathered gloves and black heels, but she totally embodied the chic, understated glamour that defined 90s fashion

They work well in relaxed work settings or casual outings with friends

Combining ease with function, it can fit nearly all events, from business gatherings to evening affairs

I love the low wedge on these embellished heels

Dont forget about the perfect red Lipstick to go with your perfect little black dress

Upon her return to the sport in 2017, eleven years after winning the tournament, she again wore a "little black dress" collaborating with Nike and Swarovski for her night matches at the 2017 US Open to celebrate her return at the championships