Even though I’m as guilty as everyone else of calling Britney a “hot mess,” I’m rooting for her. Divorce, public breakdowns, losing custody of your kids — can’t be easy. Still, there’s no denying, Ms. Brit has made quite a few mistakes over the years. And her fashion don’ts are high on the list of them.
Remember When …
… knee pads were in style? Uhhh, I don’t, which is why I can’t figure out why Britney Spears wore them at her “Baby One More Time” tour back in 1999. It was the first faux pas milestone for the pop princess.
Pretty in Pink?
At the Hollywood premiere of Crossroads, Britney Spears showed up in all pink with a hint of blue spandex. Thumbs down, Brit. It’s too matchy-matchy.
The Denim Duo
While I look back fondly at the days when Britney Spears and Justin Timberlake were a united front, I can’t say the same of this denim day for the failed pairing.
Britney is a Pimp
No words can express how truly ridiculous the outfit Britney Spears wore to the 2000 Billboard Music Awards, but let me give it a shot. The pimp-inspired vision speaks for itself. Was Britney going to an award show or a brothel?
Bondage Meets Pop Royalty
“Hey, Britney. What are you wearing to the (2002) MTV Video Music Awards tonight?”
“Oh hi, Michael. I’m going to wear my criss-crossed, laced-up pumps, a black leather dress that has a tail on the side, a matching black leather newsboy cap, and black fingerless gloves. You?”
“Britney, I’m going to wear my gold and white shin guards with black pants, and my red velvet cropped jacket with silver chains on it.”
Ummm, OK — is it just me or is this the craziest picture ever? Not even an offbeat Michael Jackson in kingdom-wear can take my eyes off Britney Spears in head-to-toe leather.