Good ol' Gwyn proves that no matter how far from fourth grade we've come, school uniforms will always have a certain charm. There's something so smart and stylish about the classic regalia mandated by private schools across America. A pleated mini skirt — just how mini depends on how willing you are to brave detention — paired with plaid looks just as classic today as it did 20 years ago, when Paltrow herself likely wore one to Spence.
When she stepped out with a friend in Soho, the goop guru wore a crisp, red plaid button-down tucked into a fluted black skirt in a midi length that definitely wouldn't earn reprimands. A color-coordinating studded red Valentino purse brought out the print of her top, while chunky black booties added a little bad-girl edge to the outfit — a handy reminder that although she still looks like she could be 18, she wasn't skipping class.