Blackwell Voted Britney Spears Worst Dressed

January 11th, 2006 // 25 Comments

Was there any doubt in your mind?

Britney Spears topped Mr. Blackwell’s 46th annual “Worst Dressed” list for wearing clothes that he said made her look like an “over-the-hill Lolita.” “When it comes to Couture Chaos, this Tacky Terror should take a bow — looks like an over-the-hill Lolita,” Mr. Blackwell said in a statement released Tuesday.

Bohemian teen tycoon Mary-Kate Olsen was the next target of the acid-tongued fashion critic. He called her clothes “bag lady rags” and “depressingly decayed.”

Jessica Simpson followed Olsen. Though her Daisy Dukes shorts landed her on the pages of numerous magazines, Mr. Blackwell said she “resembles a cut-rate Rapunzel — slingin’ hash in a Vegas diner.”

The other offenders on Blackwell’s list of fashion flops were Eva Longoria, Mariah Carey, Paris Hilton, Lindsay Lohan, Shakira, Anna Nicole Smith and Renee Zellweger.

Britney Spears Tops ‘Worst Dressed’ List [AP]

By Miu von Furstenberg

  1. Anna

    after seeing herself looking horrible and being made fun of all over the place, i’m amazed that she still goes out looking like this. that pic above is one of the worst yet!

  2. ali

    Yea, that was a toughie.

  3. One more milimeter down on those sweats & we’d be seeing her crotch. And from one big boobed girl to another, WEAR A BRA!!! Those suckers are lookin sad.

  4. QueenB

    I love the nips are no problem/I’ll almost show my coochie look.

  5. Jess

    mmmmmmmmmmmmmmmm, saggy and unsupported nursing breasts … [shudder]

  6. Paris Hilton's Hymen

    I can alllmost catch the faint smell of tuna…

  7. let it out

    interesting choice of shirt, soon to be seen at a Rehab near you…

  8. lisa

    mr. blackwell is just an old bitter queen.

  9. belle

    white trash…then, now and always

  10. doofus

    perhaps, lisa, you are right…but does that make HIM wrong? methinks not. :)

    and the above picture is a perfect example of her trashiness. and Anna, I’m with you…after all that’s been said about her appearance, you’d think she’d (at the VERY least!) wash herself, put on a bra and wear something besides sweatpants. oh, and try a little bit of acne medication! EW!

  11. Noneya

    I’m sure Mr. Blackwell never had a bad clothing day or two? It’s too bad that celebrities don’t have the luxery of walking around public looking like crap like the rest of us do. Some days its just not worth it to get all done up….

  12. jason

    noyea – even if i’m going to the corner store i put on a hat and sunglasses and make an effort to look decent; it’s a matter of pride. it would have taken just a few minutes to look better than that, without getting as you say “all done up.” i’d be embarrassed to walk around my own apartment looking that tragic.

  13. lisa


    you are right, blackwell is not wrong for brit does looks bad…it just gets to me that we hear nothing from him until new years.

    I mean when is the last time we’ve seen him…

  14. veelee

    Why are her nipples at the bottom of her boobs? That’s too bad.

  15. doofus

    ya know lisa, you’ve sure got a point…the only time he emerges nowadays is for his annual list.

    well, at least we have joan and melissa to be snarky the rest of the year.

    and jason, I HAVE to agree with you. I rarely get “all done up” for ANYTHING, but I am certainly almost always presentable and photograph-able when I go out. I don’t wear sweatpants unless I’m working out (or deathly ill), and certainly none that look like THAT! it IS a matter of pride. plus, you never know who you might run into.



  17. bestdress

    She looks awful and has been looking awful a lot. Right on Mr. Blackwell.

  18. Green Eyed Angel

    She’s the white-trash mommy who’s still yearning for her teenie-boppin sexpot days.
    And yeah, we all go out of the house with our hats and sweatpants, but one, we’re not unmercifully hounded by ‘razzi and two, she took the time to put those earings on… hmmm…

  19. Fugly Girl

    First of all, does she ever wash her hair? I think there’s about 5 quarts of oil in that rat’s nest in every picture I see of her.

    Second, if I had that kind of money I’d be paying someone to fix my makeup and hair every day.

    Third, with millions you figure the girl could buy some sweatpants that fit! I’m broke and you’ll never see me out of the house looking like that!

  20. Cristina

    Hi there I am so glad The Superficial posted this pic of Britney, because I sent them this pic … I just find it delicious :))

    - the “REHAB” t-shirt : like WHERE does she find this shirts ???
    - the expression on her face : I think she never looked more retarded than in this pic, just plane stupidity is written all over her face
    - THE FOOD ! Oh yea, the food in her hands, like she really needs MORE food ???
    - the unbrushed hair
    - the PANTS : I think they belong to Kevin lol

    Jeez … she really is a mess i almost, ALMOST pitty her.

  21. demmy

    Oh my God she really DOES have “rehab” written on her t-shirt wtf is on her mind ??!!! That is hilarious especially because she looks wasted (I mean naturally, without actually being drunk or high haha).

  22. dumdum

    demmy said:

    “(..) wtf is on her mind ??!!! (…)”

    Uhm … well… nothing ? lol

    That pic is amasing, i believe her worst so far. Big lol at the t-shirt I whould think it was self-irony (looking like shit and all) but we are talking about Brit here – and she is retarded so I cannot credit her with self-irony. It is just stupidity.

  23. Cristina

    I am sorry I said thanks to The Superficial I was reading both blogs at the time and didn`t drink my cofee yet, so …. thanks to Scocialite Life for posting the pic :P

  24. the wedding planner

    The poor thing, she’s just let herself go. Look at her, from pop something to now pooped.

  25. LuvChoo

    Alas, she’s a has been’s has been. Fat, ugly, tasteless, and sad. Somebody tell her that her perkies have perked out. No one wants to see playtex nipples through a t-shirt

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