Last night I was thinking about how exactly ten years ago I was a freshman in high school getting ready to host my first “real” party for New Years Eve 99.
I was wearing a glittery black baby tee (a size too small so it showed my belly) with extra low slung jeans and blue sketchers. I was more concerned about a certain boy flirting with my archenemy in my own basement but I do remember flinching for just a second when the clock hit midnight in case Y2K killed us all.
But it didn’t and since then the world has seen thongs sticking out of jeans, the return of leggings, JLo’s infamous green Versace, H&M arriving stateside, Bjork’s swan, the “It” bags and their subsequent waiting lists, and Carrie Bradshaw going from TV character to fashion icon.
In honor of the fashion tragedies and iconic moments here are my favorite ten looks from the past ten years…
Michelle Williams in Vera Wang
Kirsten Dunst in Rochas
Camilla Belle in Jean Paul Gaultier
Mary-Kate Olsen in Balenciaga

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Cameron Diaz in Chanel Haute Couture

Side Note: I’m not a big fan of Cameron Diaz and I’m normally not impressed with her fashion choices but I was OBSESSED the moment she stepped onto the red carpet in this Chanel. I love mini dresses and the nude shoes were a stroke of genius. The button detailing down the back is just beautiful and I love that the lace is sheer in only the right places. This is still my dream red carpet outfit-you know, if I’m ever on one!
Chloe Sevigny in YSL
Cate Blanchett in Armani Prive
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Reese Witherspoon in Nina Ricci
Side Note: I was really hesitant about putting Sarah Jessica Parker’s Chanel Haute Couture because I think there is a lot wrong with it. But the thing is this dress is just the epitome of SJP’s red carpet style and when she’s “on” she’s the epitome of what I think everyone wants to see in fashion: A fun, frothy dream.
Anne Hathway in Atelier Versace


  1. Ooo…I love Reese Witherspoon's yellow dress! I also really liked Natalie Portman's dress for the last Academy Awards. It was a perfect color for her.

    Your blog is so cool!

  2. i think reese is my favorite for cocktail length and michelle is my favorite gown. good choices!

  3. All of your top pics are exactly what I would've chosen. Love them all!

  4. Love all of these, especially all the blondes in yellow. Sweet! Thanks for reminding me about dresses I'd forgotten about.

    Oh, and be sure to check out my handbag giveaway!

  5. Bostonista

    Thanks guys! I'm glad you like my choices!

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