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To do so, pair a mini sweater dress with sleek knee-high boots (this shoe style leans more formal)

Unlike plain athletic jackets, Y2K windbreakers often had oversized fits and bold color blocking that made them more streetwear than sports gear

See below for 20 picks that'll win you best-dressed every single time

Celebs like Pharrell and Fred Durst wore them with tees and sneakers, making cargo shorts an easy foundation for relaxed Y2K outfit ideas

What You'll Need : RBG Dissent Collar Necklace, $11, Amazon 10 Serena Williams Jean Catuffe Images Advertisement - Continue Reading Below 11 Katherine Pierce from "The Vampire Diaries" The CW Your individuality complex may balk at dressing up as a vampire for Halloween