Best Bet: Friends & Associates Alexa Bib-Front Dress

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Matthew Edelstein is better known for his men's styling work at Details and InStyle, but now he can add designer to his résumé. His line, Friends & Associates, is a colorful interpretation on classic uniform pieces: skirts mimic waitress aprons, pullovers riff on sailor tops, and playsuits are reminiscent of workwear. One standout is this bib-front dress that incorporates sharp tuxedo pleating but adds a colorful pop with a bright blue collar. Throw it under a blazer for a creative take on a suit or simply wear on its own once the weather warms up — it certainly isn't meant for a stuffy black-tie affair.

Friends & Associates Alexa bib-front dress, $165 at Friends & Associates.