1. Home
  2. Style
  3. Women's Fashion

Worst Dressed for 1999

Mr. Blackwell's list

By , About.com Guide

***Click through to this year's Worst-Dressed List for 2003***

It's the 40th anniversary of Mr. Blackwell's enormously popular 10 worst dressed list and somehow it seems a fitting tribute that the madame of outrageous dressing, Cher, should top the list, edging out last year's No. 1, Linda Tripp ("She looks like a sheepdog in drag")

No one is safe from Mr. Blackwell's barbs, who said in 1967, Elizabeth Taylor "looks like two small boys fighting under a mink blanket." This year he skewers good taste icon Martha Stewart, teen queen Britney Spears and even Queen Elizabeth (again).

The 1999 worst dressed list, along with Mr. Blackwell's comments (see resources)

1. Cher (Also No. 1 in 1984)

"A million beads and one overexposed derriere.""The ultimate fashion fiasco."

2. Celine Dion

"In her backward tuxedo there's no way of knowing whether Diva Dion is coming or going - a profusion of confusion."

3. Queen Elizabeth (Also on the list in 1990)

"Was she the palace Christmas tree or just a royal clown?" "I've seen a lot of queens, but Queen Elizabeth is the worst!"

4. Martha Stewart

"She dresses like the centerfold for the Farmer's Almanac."

5. Fiona Apple

"A kinked and curled Kewpie Doll wrapped in a collection of yesterday's fatal fashion frights."

6. Britney Spears

"This belly-baring songbird is better heard than seen."

7. Sarah Jessica Parker

"From 'Sex and the City' Sarah's fashions are a mix-and-match pity."

8. Jennifer Aniston

"She's a fashion bore and a snore.""Brad Pitt looks better in a dress than she does!"

9. Cameron Diaz

"On 'Any Given Sunday' Cameron falls prey to a freaky fashion curse - and as the week continues, she just slips from bad to worse."

10. The Dixie Chicks

"They look like a trio of truckstop fashion tragedies trapped in a typhoon."

Mr. Blackwell also does a est dressed list, but it's not nearly as much fun. This year's winners:

  1. Princess Caroline of Monaco
  2. Gwyneth Paltrow (Also, best dressed in 1996, 1998)
  3. Sophia Loren
  4. Oprah Winfrey (Also, best in 1998)
  5. Camryn Manheim
  6. Sophie Rhys-Jones
  7. Barbra Streisand (Did her time on the worst-dressed list. In 1967:  "Today’s flower child who has gone to seed in a cabbage patch. 1969: "Yesterday’s see-through...chemise, schlemeil, and 23 Skiddoo, and what happened to you?" 1983:" A boy version of Medusa"; 1984 "The Al Capone look with electrocuted hair!"; 1986: "A shoddy Second-Hand Rose looking for a tour guide in Brooklyn"; 1990: "What can I say? Yentl’s gone mental!")
  8. Halle Berry
  9. Helen Mirren
  10. Nicole Kidman (Also 1995)
  11. Sharon Stone (Also 1994, 1995)

Explore Women's Fashion

About.com Special Features

Holiday Central

What to eat, where to go, fun things to do and how to save money on the perfect gifts. More >

Fall Fashion Accessories

These hot fall accessories will update your wardrobe without breaking the bank. More >

  1. Home
  2. Style
  3. Women's Fashion
  4. Celebrity Style
  5. Best/Worst dressed lists
  6. Mr. Blackwell's 1999 Worst Dressed List>

©2009 About.com, a part of The New York Times Company.

All rights reserved.