1. Angelina Jolie giving us velour gothic realness. Albert Ortega / Getty Images Cable Ace Awards, '97. 2. A spiky haired Winona working the "deer-in-headlights-pleather" goth vibe. Brenda Chase / Getty Images Premiere of Alien Resurrection, '97. 3. "I just woke up and I'm still sexy AF" look from a young Keanu Reeves. Dan Callister / Getty Images MTV Movie Awards, '99. 4. Jada Pinkett Smith looking pretty fuckin' cool. Brenda Chase / Getty Images American Comedy Awards, '98. 5. I could write an 800 page book based on this picture alone. But instead, I'll say two words; those glasses! Handout / Getty Images CDDB awards, '99. 6. The "hahahaha you're not funny" look, courtesy of goth queen Helena Bonham Carter. Brenda Chase / Getty Images Golden Globe Awards, '98. 7. Queen Latifah and Danny DeVito giving us the most iconic photo of all time. LOOK AT IT! Dan Callister / Getty Images Premiere of Living Out Loud, '98. 8. Fairuza Balk and David Thewlis nailing the "awkward goth couple" vibe. Albert Ortega / Getty Images Premiere of The Saint, '97 9. Drew Barrymore looking like Courtney Love's long lost family member. Jon Levy / AFP / Getty Images MTV Video Music Awards, '95. 10. Sarah Michelle Gellar just purely channeling Buffy with that leopard print skirt. Albert Ortega / Getty Images Premiere of The House of Yes, '97. 11. Sandra Bullock giving us the "is that the person you hate?" look. Relatable. Brenda Chase / Getty Images 25th Annual People's Choice Awards, '99. 12. Lucy Liu giving us all outfit envy by looking sleek and chic. Brenda Chase / Getty Images Premiere of Play it to the Bone, 2000 (January 2000, that is, which was pretty much the '90s – lemme have it!) 13. '90s goth couple award goes to Rose McGowan and Marilyn Manson. Lucy Nicholson / AFP / Getty Images Premiere of Sleepy Hollow, '99. 14. Here's Madonna in her ~ethereal~ Ray of Light era, working a tight bondage-esque outfit. Vince Bucci / AFP / Getty Images Annual Fire and Ice Ball, '98. 15. Then we have Christina Aguilera just being...very '90s. Henny Ray Abrams / AFP / Getty Images MTV Video Music Awards, '99. 16. Neve Campbell being pure '90s perfection. Brenda Chase / Getty Images Showing of the 100th episode of Party of Five, '98. 17. "I run the world, I am kween Céline." And it's still true. Vince Bucci / AFP / Getty Images LA Shrine Auditorium, '99. 18. Natalie Imbruglia looking very '90s with a red eyeshadow look, and a huge ass gramophone. Mike Nelson / AFP / Getty Images Annual Grammy Awards Nominations '99. 19. Lauryn Hill looking amazing in a red pleather shirt. Fair play Lauryn, fair play. Henny Ray Abrams / AFP / Getty Images MTV Music Video Awards, '99. 20. Baby Leo and Kate were looking very dashing. Kate's face is also just very relatable. Hal Garb / AFP / Getty Images Annual Golden Globe Awards, '98. 21. And finally, Whoopi broke the '90s with this fantastic Velvet Goldmine look. Timothy A. Clary / AFP / Getty Images 71st Academy Awards, '99.