Aisha’s Fashion Faves is a love letter to the clothes that raised a generation: the sparkle and excess of Y2K, the slouch and swagger of the 1990s.

Expect Y2K rhinestones, baby tees, low-rise denim, butterfly clips, velour and full-throttle maximalism. Expect 1990s double denim, grunge, street style and the Canadian tuxedo. And expect plenty of personal stories from Chicago department stores, where Levi’s, DKNY, Calvin Klein and Guess, plus overalls and preppy styling, shaped how I dressed and who I wanted to be.

Every story here is part fashion history, part memory, and all opinion. Pull up a fitting-room mirror.