In Michael Bolton’s Big, Sexy Valentine’s Day Special, singer Michael Bolton is tasked with encouraging couples to make love and make 75,000 babies, in order to clear the excess inventory of toys in Santa’s workshop. When all seems lost, he activates Peak ’90s Bolton, golden locks, denim suit, and all, which pushes the making babies count over the top.

Steven Q. Urkel, played by Jaleel White, lives next door to the Winslows on the TGIF show Family Matters. Urkel is the ultimate nerd with his awkward fashion, high-pitched voice, and unrequited love for Laura Winslow — at least until he drinks his cool juice and transforms into Stefan Urquelle.

Lisa Loeb became America’s sweetheart when she burst onto the music scene with her song “Stay.” While she may be considered a one-hit wonder to some, her style has managed to stick around. While dressing in all black is simple you really need the tortoise shell cat eye frames to make this look work. Otherwise people might just think you’re a beatnik.

Now this is the story all about how Will Smith’s life got flipped, turned upside down. He plays a street-smart teenager in The Fresh Prince of Bel-Air, who is sent from his West Philadelphia home to live with his rich relatives in Bel-Air. He brings with him his unique sense of style, often wearing colorful prints with matching hats.

Andrew WK is a rock singer and songwriter known for his hit single Party Hard, and for partying hard. This outfit just needs one more thing — for you to wear the jeans seven months straight to build up that grime.

It was the year 1994 when former pro wrestler and movie star Dwayne “The Rock” Johnson reached peak ’90s fashion, decked out with chain necklace over black turtleneck, gripping a brown leather fanny pack. Don’t forget a pack of tissues so you can keep your turtleneck spotless while leaning casually against various backdrops.