Yes, the 2000s had its share of regrettable style moments and seriously low points (lest we forget the brief romance between Paris Hilton and Nick Carter), but that hasn’t stopped fashion’s current obsession with that era’s questionable-yet-somehow-amazing brands and logos. Love it or hate it, Fila, Kappa, Juicy Couture and, yes, even Von Dutch are back and tugging at our The O.C.-loving, oops-they-did-it-again heartstrings. Feeling nostalgic for trucker hats and velour? Click through our trash-tastic ode to all the so-bad-they’re-good throwbacks—complete with Microsoft Paint-inspired then-and-now moodboards (because the Y2k aesthetic is just that lit). For maximum enjoyment play this classic track in the background, then go pick up these retro gems before they go bye bye bye (again)!
What would the ’00s have been without the trucker hat? Originally donned by the likes of Ashton Kutcher, Tara Reid and Britney Spears (a.k.a. 2000s royalty), the Dutch crown now belongs to this generation’s pop culture princess, Kylie Jenner who’s posted multiple photos of herself rocking the brand. If you (rightly) trashed your cap along with your Pussy Cat Dolls concert tee, don’t worry, they’re now available at your local TOPSHOP.