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The Player , 1992

The Poetic Justice star tucked a long-sleeved boatneck tee into a belted pair of mom jeans and wore a newsboy cap over her long box braids

Mandy Moore The actress and singer showed off a matching graphic set in 1990

And even if you cant spring for a real leather blazer, there are a ton of convincing vegan leather options out there

The trick is to treat them like anything but a precious grail: buy 'em in black, and dont be afraid to beat those sturdy soles into the ground

A scarf worn as a choker

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