Celebrity Transformations

by SheKnows
May 19, 2010 at 3:45 p.m. ET
Image: WENN
Ashlee Simpson has transformed herself and her sense of style into a softer, more polished look.

1 /32: Lil' Kim

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1/32 :Lil' Kim

Lil' Kim is almost unrecognizable today when compared to her mug shot.

2 /32: Michael Jackson

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2/32 :Michael Jackson

Michael Jackson was the quintessential example of a transformation gone wild.

3 /32: Nicole Richie

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3/32 :Nicole Richie

After babies Harlow and Sparrow, Nicole Richie looks happy and healthy.

4 /32: The Olsen twins

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4/32 :The Olsen twins

The cute and sweet Olsen twins have developed an interesting sense of style over the years.

5 /32: Peter Jackson

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5/32 :Peter Jackson

Director Peter Jackson is almost unrecognizable after a tremendous weight loss.

6 /32: Taylor Swift

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6/32 :Taylor Swift

Taylor Swift has gone from awkward teen to country sweetheart.

7 /32: Kim Kardashian

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7/32 :Kim Kardashian

She went from fashion zero to fashion hero — well done, Kim! Even while pregnant she's managed to stay dashing.

8 /32: Sarah Jessica Parker

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8/32 :Sarah Jessica Parker

Sarah Jessica Parker has held on to her "Carrie" style since Sex in the City — and we love it!

9 /32: Natalie Portman

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9/32 :Natalie Portman

Natalie has found a better stylist since her younger red-carpet days.

10 /32: Wendy Williams

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10/32 :Wendy Williams

Wendy has learned how to dress more flatteringly and looks red-hot.

11 /32: LeAnne Rimes

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11/32 :LeAnne Rimes

LeAnne Rimes' hair alone has undergone an amazing transformation over the years.

12 /32: Kelly Osbourne

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12/32 :Kelly Osbourne

Kelly Osbourne now looks happy and healthy.

13 /32: Katie Holmes

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13/32 :Katie Holmes

Since meeting (and divorcing!) Tom Cruise, Katie Holmes has turned into a style icon.

14 /32: Donatella Versace

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14/32 :Donatella Versace

Donatella Versace has had one too many procedures!

15 /32: Carrot Top

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15/32 :Carrot Top

While always slightly bizarre-looking, Carrot Top looks just plain weird today.

16 /32: Carrie Underwood

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16/32 :Carrie Underwood

Carrie Underwood has transformed from cute to glamorous in just a few short years.

17 /32: Evan Rachel Wood

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17/32 :Evan Rachel Wood

Formerly fresh-faced Evan Rachel Wood has taken a turn toward the dark side.

18 /32: Fergie

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18/32 :Fergie

Fergie looks as if she may have had a wee bit too much Botox over the years.

19 /32: Heidi Montag

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19/32 :Heidi Montag

Before meeting Spencer, Heidi Montag was once normal and cute.

20 /32: Holly Madison

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20/32 :Holly Madison

Holly Madison has gone from high-school rebel to Hollywood hottie.

21 /32: Janice Dickinson

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21/32 :Janice Dickinson

Janice Dickinson, the self-proclaimed "world's first supermodel," now looks less than super.

22 /32: Kate Gosselin

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22/32 :Kate Gosselin

Eight babies, a reverse mullet and a divorce later, Kate Gosselin now looks amazing!

23 /32: Elliott Yamin

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23/32 :Elliott Yamin

Elliott Yamin's style (and teeth) have come a long way since his American Idol days.

24 /32: Rupert Grint

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24/32 :Rupert Grint

Rupert tamed his red mane and now looks a lot more put together.

25 /32: Kelly Rowland

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25/32 :Kelly Rowland

Kelly kept her sleek black dress choice, but managed to prove just how much she has grown up over the years.

26 /32: Kate Moss

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26/32 :Kate Moss

Kate Moss has only gotten more fierce with age.

27 /32: Emma Watson

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27/32 :Emma Watson

Emma has transformed into a gorgeous young woman right in front of our eyes.

28 /32: Jennifer Hudson

Image: Carrie Devorah / WENN; Ivan Nikolov / WENN.com

28/32 :Jennifer Hudson

This beauty has always been an advocate for curvier women, and is now at a very healthy weight.

29 /32: Jonah Hill

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29/32 :Jonah Hill

Jonah Hill has made an amazing change in his overall appearance.

30 /32: Chaz Bono

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30/32 :Chaz Bono

Once Chastity Bono, Chaz has made a great transformation into the man he always knew he was.

31 /32: Jordin Sparks

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31/32 :Jordin Sparks

The American Idol winner looks slimmed and sexy.

32 /32: Seth Rogan

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32/32 :Seth Rogan

The funnyman seems to be healthier & happier now-a-days.