Retro Snap: Who Had This Regrettable Fashion Moment?

kelly osbourne

I normally love everything this woman wears…

And she made me want to dye my hair grey more than anything else in the world. But not this outfit! This is horrible. Well, you’ve come a long way, Kelly Osbourne.

Here she is more recently:

kelly osbourne

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    • sara

      I feel like in another 5 years, she will probably be unstoppable in her fashion choices. She still has flubs here and there, but her choices are NEVER boring.

    • L

      every week i watch the fashion police and think to myself, “how has Joan not drugged her into a stupor and dyed her hair a normal color yet?!?!”

    • Lindsey

      That outfit is uncomfortably close to things I wore in high school.

    • Sarah!

      I loved The Osbournes SO MUCH. I wanted to marry Jack and be best friends with Kelly. Seriously. I even defended her cover of Papa Don’t Preach. LOVED IT.

    • Stella

      I think that first outfit is entirely appropriate, pretty cute junior-high or high-school get-up, not horrible at all. If she were still dressing like that today, well, yes, maybe that wouldn’t look so good. I still like the old lipstick better than the new, though.

    • Cassandra M.

      I love her old look so much better. She looks ridiculous most of the time now. Who the eff dyes their hair gray at her age? And she tans now! Ugh, such decline.