What's Jessica's Best Look: Sexy or Conservative?

09/12/2008 at 12:21 PM ET

Most Wanted/Flynet(2)

Just because she is returning to her country roots with her new album, doesn’t mean Jessica Simpson has lost her sexy image. The blonde bombshell entered the The Late Night with David Letterman show in a business-like black satin Diane von Furstenberg dress with a loose updo and conservative brown Jimmy Choo pumps. On the way out, the singer let her hair down and slipped into a seriously body-hugging Herve Leger dress. Jessica is proving to be an ultimate style chameleon the way she changes back and forth from country conservative to city sexy — in the same night! Tell us: What do you think is Jessica’s best look: conservative or sexy?

FILED UNDER: Jessica Simpson

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Showing 19 comments

erica on

she actually looks better sexy! but the sexy pic is conservative and classier than most of her usual sexy looks!

M.T. on

Sexy is much better. conservative makes her look
older and drab.

bez on

i think she jt gained some weight and black is the best way to hide it and look elegant.

Pamela on

She looks good both ways, but I think the sexy Herve Leger dress might be a bit tight.

amy on

She looks way better sexy because her voluptuousness is the main thing that makes her look attractive. When it’s covered up (as in the conservative photo), the attention is drawn to her face and hair which aren’t her strengths.

Tas on

I think Jessica looks best when keeping her mouth shut! I saw her Letterman appearance and she was terrible. She’s still trying to cash in on the naive, dumb blond act, and it fell flat. The audience was laughing AT HER, not WITH HER. And don’t even get me started on her singing. Did anyone see her on THE VIEW? AWFUL! It’s time for this no-talent stupid girl to go away. What she wears is irrelevant.

Rebecca on

I think that Jessica looks better conservative because it makes her look more mature, and putting all the silly stuff behind her. You look great Jessica!

lily on

Who cares what she wears? I am so sick of this no-talent, bubble head (and her little dog too).
Stop photographing her! She is way beyond her 15 minutes of fame. I wish she would just go away and never be heard from again. Same goes for her idiotic, even less tlented (not easy to be) sister.

Morghan on

i think she looks conservative. And when she was fighting with Carrie Underwood, i thought it was funny that she said she is much prettier. Carrie Underwood has more talent and is much prettier Jessica is just JEALOUS!!!!!!11

Thank You

Dorothy on

Both looks are great. The sexy look is toned down and it is very subtle sophisticated sexy look.And the conservative one shows some cleavage as well as the dress is very form fitting so it shows her curves. Those are the best looks a have seen of Jessica in while.

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