Everyone may be obsessed with the 90s now, but the late 1990s and early 2000s, had a lot of WTF outfits courtesy of our favorite boy bands and pop princesses. Justin Timberlake and his *NSYNC boys, made up about 32% of the crazy looks. Why Justin wore some of these outfits, and why we thought they looked good is another big mystery of life, just like how no one is still sure of the spelling for N Sync/NSYNC/*NSync/’N Sync, etc.
Get ready to party like it’s 1999, here are 12 WTF Justin Timberlake outfits:
Hang on, is that a triple denim outfit? As strange as Justin’s patchwork denim jacket is, I think JC and Chris’ mixed fabric denim jackets are actually worse. Velour?! Shimmery snakeskin?!
Was this really considered an improvement to the bleached Ramen Noodles curly hair?
Reason 3,532 why Justin should never wear denim again. I don’t know what is worse: the white cords coming out of his crotch, the leather patches, or the fact that they are hemmed and he’s stepped all over them.
Justin’s look was gradually improving, but he did not yet have the fashion cred to rock a pair of fingerless gloves–and he still doesn’t. Only Madonna has that privilege.
Oh my, 1999. You can’t really blame Justin for this one. Clearly, *NSYNC’s wardrobe theme was “steal your father’s blazer and wear it on the red carpet”–unless Justin chose this theme, then we’ll blame him.
Did Justin suddenly think he was going to join a pop punk band? Or maybe he was trying to get a date with Avril Lavigne? Those are the only reasons that would explain that checkered wristband.
Poor Justin wanted to be Michael Jackson so bad. Instead of wearing a red leather jacket, he ended up wearing a red scaly leather turtleneck, and looked like he was wearing half of a lizard superhero costume.
A small part of me still wishes that Justin and Britney would get back together, because they always came up with wacky outfit ideas. Memories.
Wow, there are so many things that aren’t quite right with this, that my eye doesn’t know where to focus. I will look past Chris’ tie-dye and paisley mix, and JC’s hat, and focus on Justin’s hair. Wait, is that a ruffled leather shirt?
How could we forget about the double denim monstrosity that occurred, that to this day, remains the biggest abomination in denim, beating Katy Perry and Riff Raff‘s valiant effort?
Hang on. Is this really Justin or is this Laird from Girls, aka Hannah’s downstairs neighbor?
(Photos: Getty Images, WENN)