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While Ill never knock the gal who really goes for it and pairs together items that really make no sense (sometimes it works, sometimes it doesnt), there are a few key things to keep in mind to ensure your minidress and boots dont end up looking like a 60s Mod costume

While some Y2K trends were worn daily, many of these looks were reserved for going out

Designed with a sleek and unique mermaid silhouette, this dress is sure to make a statement

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The recommendations below include trousers for the proportionally blessed and the smart-looking pair a Strategist staffer wears when she commutes on her bike