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But as cool and trendy as they look on celebs and street style stars, they can be an intimidating piece to style

We are seeing a resurgence in Y2K outfits, so chances are you will find yourself at a themed party surrounded by low-rise jeans, butterfly clips, chunky sneakers and metallic fabrics

It can pair well with any neckline, sleeves/straps, fabrics, and train types

Artists like Jay-Z, Missy Elliot, Lil Kim and Aaliyah were driving forces behind the merging of streetwear and high-end luxury, a staple of the Y2K aesthetic

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

Color Polo Brown Dress Calf Leather