What Was She Thinking? Jessica Simpson at the Teen Choice Awards

08/21/2006 at 04:47 PM ET

Was Jessica Simpson so consumed with the stress of hosting an awards show that her ex-husband and his new girlfriend were both nominated for that she ignored her wardrobe? Jessica is known for being a clothes horse and an avid shopper, so we’re a little surprised at her lack-luster wardrobe on the show. From the see-through Jill Stuart lace shorts one-piece (left) to the unflattering tulip-skirted Miu Miu dress (middle), Jessica looked off her usual style standards. The satin bustier paired with baggy cargo pants and heels (right) veers into the inexplicable, leaving us scratching our heads. Still, Jessica did a good job handling awkward hosting duties. If only her outfits had as much grace.

To see more of Jessica click here

Photo: Frank Micelotta/Fox/Getty;Michael Yarish/FOX;Kevin Mazur/WireImage

FILED UNDER: Jessica Simpson
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Showing 101 comments

Brian Belovitch on

Just awful. Poor Jess is a mess. She needs a total makeover, starting with the over extended hair!

marianne on

I am not even going to talk about the clothes, they speak for themselves (disaster!!) Jessica needs to lay off the self tanning lotion, the over done make-up, the hair extensions ASAP… she looks ridiculous!

Mary on

I love Jess, love her hair–
These are unflattering photos, she is still a gorgeous girl.
She just needed some better dresses–
And the shorts were not flattering.

Megan on

Terrible! And so overrated!

~Andrea~ on

Ok …wait a minute here… what is going on Jess? I’m just so confused with these choices. Why when you have endless picks of Top Designer clothing would she choose these outfits that make her look about 10pds heavier and just so not cute or flattering! And I’m sorry but, Ken could have hooked up her hairstyles a little more..or less. I just think this was a bump in the road of fashion for Jess. I think she is usally stylin and to me the less she tries the better she looks. …….And come on girl,you don’t want your Ex’s girl to look better than you do! Get it together! It’s a Public Affair :):)

cate on

wowie. thats terrible. what was she thinking? i mean seriously who would go out in public like that?

Kacie on

I love Jess! No matter what her hair or clothes are doing, she always looks so gorgeous! While she maybe could’ve chose better outfits, she still looks better than most the people out there! And, are you crazy? Like Nick’s new girl ever looks better than Jess!

Jessica on

Unflattering, tacky, and overdone – just like the rest of her!

roxyseabreeze on

“so sad…she is so pretty…but these pictures did her no justice! Sorry to say but she has had better days…and this day sure wasn’t one of them!!!

bettyboop on


Brianna on

I don’t Know What Jess was thinking but what I do Know is that the fist outfit choice should have had a warning sign posted on it. The others are still pretty bad but not as bad.


What was Jess thinking when she picked these FUGLY OUTFITS!!! Jessica is so pretty, but with the outfits she looks awful. Not to mention TACKY all over!

krystal on

i think she looks horrible. Whats with stars and their style these days its just nasty!!!

Debbie Price on

Not only were Jessica’s clothes awful, but she had on wayyyy too much eye makeup. My husband said she looked like a “lady of the night.” I don’t know what she was thinking! She is such a pretty girl and she just looked terrible on that show.

trintica on

Those ARE unflattering photos…and those outfits are probably not her best choice. But she is usually a fashion icon for the younger generation and i love her and her style. she is a gorgeous woman and i admire her so much!
[too bad about that black bag-dress though.]

Courtney on


Courtney on

Wow….i guess its true that when you get divorced it really drains you. I didnt know your fashion sense got washed out too but Jessica made it quite evident that it does go as well.

erika on

from the comments so far, ppl are always like “what is she wearing? why are these fashion choices not like her usual ones?” maybe it has something to do with her sister and her sister’s ever-changing style…maybe she opted for a bit of a change that would cause some buzz as opposed to sticking to her usual safe style…i guess fashion is about trial and error…you see what works for you…i’m sure there is a reason she chose these outfits, even if not the most flattering…maybe she was just trying to cause a stir…i never really liked her style at award shows in general…

Secret* on

Well I love Jessica her clothes where not the best choice but she probably had alot distracting her poor thing just imagine having to be in the same ROOM AS YOUR EX AND HES PLACED RIGHT IN FRONT OF YOU!!! plus no matter what she still looked beutiful goes to show she can make anything look good and she has nothing to worry about Nicks new girl looking better than her because Jess is sooooooooo muuuuuuuuuch better!

melissa on

Ok, this is another example of someone trying too hard. She has no taste or whatsoever…Jessica Simpson, everything about your look is fake, from the orange skin, the fake lips, the huge hair extensions…the outfits are so unflattering…is exhausting just looking at you ! C’MON…were does all the money go to???

Tina on

She looked awful. Her fashion choices were all wrong. And Dane should have taken over hosting duties for Jessica. She was horrible.

Jen on

I don’t like any of her outfits or hair in these pictures! I mean it’s just my opinion, others may like it, but it’s just not my style.

Cyndi on

Sorry to say it but she looks like a skank, and a poorly dressed one. I don’t know what kind of sex-tramp statement she is trying to make since her divorce but it isn’t working AT ALL!!! Nick was lucky to break free of this spoiled, childish, ridiculously stupid vamp.

Alexa on

Jessica looked absolutely stunning. Her outfits were very cute and classy. All of you who disagree, it is out of jealousy. She looks damn good, and you all wish you looked as good as her.

Alicia on

I used to be a big fan and she is a beautiful girl no matter what she wears…but lately, I am just really sick of seeing her. No matter how she is dressed-I just don’t want to see any more of this girl for quite some time.

kelly on

Forget the clothes, who gave her two black eyes? She should fire her makeup artist as well as her stylist. And she was HORRIBLE as a host. No timing, not funny, not cute… Nick was better in his two second acceptance speech than she was all night.

Jill on

I am so glad that someone said something about this. I couldn’t believe what I was seeing when I tuned in yesterday. I thought she looked really awful and I really didn’t think she did a good job of hosting. The last shorts outfit was ridiculously unflattering. I agree with everyone else – for a known trendy, clothes horse, this is inexcusable and unexplainable. I think she just looks “worn” and definitely not as fresh faced as she did in the recent past.

Nick, on the other hand, looked great. I think he’s great.

Erin on

the first and third make her look like a hooker!
mostly the third.
the second one is cute but her hair needs some frizz-ease
and a comb through its not the 80’s the fro died along time ago along wiht her relationship

Aymer on

Did you get dressed in the dark????

ann marie on

I agree her outfits were just not flattering. jessica is a beautiful girl and she looks better without the heavy eye make up and long hair extensions. I mean she is a fashion icon for many but clearly this was not her best night

messy jessy on

here clothes were terrible, but her hosting job was even worse… she looked so dumb. even k-feds terrible performance was better then her

Sara on

So incredibly hideous

a-non on

The good thing about Jess….she’s comfortable in her skin…clothes are just another layer for us to judge. I say good on ya Jess for your confidence!

kim on

She just seems like she was trying to do something a little more edge-y, and didn’t quite pull it off, knowing that it was a teen show, she tried to dress down and still be glamorous, I guess it didn’t work. As for the people who keep pining for Jessica and Nick to get back together, why? how ridiculous! They were just another hollywood couple, what made it seem as though it should last? The root of all separations is selfishness and who better to get on with their selfish selves than a couple of rich, young, hollywood people who think their choices actually matter to everyone else in the world.

Krissy on

First of all no one can always look perfect. And second of all maybe she was just trying something different with confidence. Everything is always worth the try especially if you have the confidence. Even though I think Jessica Simpson is a really pretty girl, she looks the prettiest when she just has that natural look. Less makeup, no hair extensions, just normal ole Jessica.

molly on

jess must be trying very hard to “look” better nwo that she’s divorced
but she’s trying too hard! lose the extra hair! lose the extreme makeup! and just dress like a normal person for goodness sakes!

Mary on

No she was not thinking right, her clothes did not look right. Her make-up was a mess come on is she doing a movie for Dawn of the Dead. As for hosting she made herself look real dumb again. Your trying to hard to make the public like you. You make the old saying about Blondes look true. Give it up.

vm on

I would never desire to look like JS in any of these photos. It’s a joke to say any of the comments that give honest criticism are a result of jealousy. Jessica went to my highschool and she was a raving cutie. Hot! Over the last year she has become less and less attractive. Like she is trying to disguise something. Yes, a clown is about how she looks in all these photos. Go back to the real you! You never needed hair extensions, bleached out teeth and hair, or fake eye lashes in school and you glowed when you walked down the hall. This is just bad KUNTRY!

Shannon on

Normally I think Jessica Simpson dresses cute, however she was a joke as the host last night. Her clothes did now suit her and she flopped! She needs to lay off the self tanning and be herself again. As for Nick well he always looks good. I don’t like one more than the other but she is going through something that we don’t know about. She has never really been able to be young. She is 25 but was with someone older than she is for a very long time. So give her a break. Let her be free for once in her life.

Neringa on

I don’t know why you guys love her so much. I find her very unpretty, I even would say ugly… And her new song “A Public Affair” – it’s so pop and don’t show her voice’s potencial. So what’s the fuss about her?

Katie on

I think Jessica Simpson’s style is amazing, but she definatley didn’t show it at the awards compared to Jessica Alba’s flattering and beutiful outifts when she hosted the MTV Movie Awards. Anyway, Jessica could have done better with her hair and she also looks a little overcooked, as in she should lay off the self-tanner. Also her makeup was hideous, the ugly black all over her eyes wasn’t flattering at all. She should has gone with a more natural look. But I

brooke on

OMG… what happend? she does look awful in those clothes. But what am I reading? poor jessica for having to think of her ex and his new belle? WHATEVER! she decided to divorce him..what do you think she should have expected? that he would never date again and dissapear? No NO… not an excuse for this terrible choice of outfits and look. There is not one thing flattering about these clothes, her hair, make-up or tan. Jeeeezzzz she’s such a beautiful girl ussualy with a great fashion sense…why ruin it by trying out stuff your grandma could’ve told you looks just ugly. hahahahahahaha

Julie on

Jess looked very tacky & cheap.Nick looked as beautiful as ever.

michelle on

Nick was ALWAYS way too hot and classy for this “girl”….she is immature and needs to grow up. I think Nick saw that, and I’m glad he did!! He’s beautiful and she is just plain trashy!! The hair is ridiculous and the make-up and clothes are hysterical!! I cannot believe someone would actually leave their house like that! Hey, Jessica, where’s your mirrors?? KUDOS to Nick!!!

Leni on

Yikes…each look is so overdone and completely wrong. She needs an intervention STAT.

Candace on

HOLD UP! Now, all you haters can stop right now … everyone has their bad days .. and Jessica is a normal human being. I completely agree that her choice of outfits probably wasn’t the greatest, but I’m sure there have been times were you guys haven’t looked so hot in what you are wearing … we all have those days. Jess is a natural beauty, and I also agree with the comment about being too done up. She needs to realize that she is a beautiful girl and she doesnt need all of these extras to look pretty! She’s going through a rough time with her divorce, and now her little sister is making headlines with her ever-changing style, she was probably just experimenting with something new so that she could be in the spotlight, once again.


SHE IS SO CUTE AND I LIKE HER CLOTHES (STYLE), HAIR, yes everything… / A girl from SWEDEN, europe ;b

Faith on

forget the awful clothes, did anyone else notice how fake and ditsy her acceptance speech was near the end of the show? Barf! I don’t know if it was nerves or what, but it seemed like she was really laying on the airhead act THICK. And the more she talked, the wider her blackened eyes got, and the dumber she sounded. And the audience was quiet…not laughing. I just think for someone who has repeatedly said in interviews how high her I.Q. is, and how smart she is, she should act like it more. She is a beautiful girl, and she doesn’t have to act dumb to get attention. I guess she hasn’t realized that yet, but either way, the extreme airhead act is getting old.

jessica on

i think she looks good but the last pic is not a look she should wear again….sorry, u do look good thought.

Shila on


j.j. on

it’s the hair that makes her look like a drag queen!

kristy on

I think jessica looked terrible in the first two outfits. The last one isn’t SOOO terrible. I give her a 6 for the evening. She looked very exhausted so she probably was clustered and didn’t really pay too much attention to her style. She should have though, I mean…Nick was there. Show him what he is missing ya know?

Ericka on

The girl needs to update her looks. Change the hair, have more personal style. Someone help her, and stop plugging herself so much. its embarrasing.

Nadia on

She has looked soooooo much better! She is totally loosing her fashion sense. It’s seems like she is trying to hard too look good and it aint happening.

Patricia on

Im not big on the clothes but I like her hair. I think she is one of the only people who can pull off all blonde.

Kimberly Fierro on

She’s really trying way to hard. With her looks she can make the simplest outfit look glamorous. She needs to go with a more polished look.

Bre on

Wow!! I didn’t see the teen choice awards, but from the looks of these pix she def. got worst dressed at the show!! lol.I think she is beautiful but needs to relax with the tanning and makeup, The really sad part is that these outfits probably cost more then my house and they are realllly realllllllly gross!!

Megan on

im not quite sure if you people have any clue who hate jessica what yall are talking about. she is FREAKING absolutely GORGEOUS, if you think she isnt you are just jeaouls and cant accept the fact that she is one of the prettiest women in the world!…and dont say nick deserves better…were you there with them EVERY second…what did you see except for what was on TV? I think jessica deserves better….and she doesnt look that bad…she is ALWAYS gorgeous…and whats wrong with wearing something that isnt too flashy…or something somewhat normal? last time i checked…there was nothing wrong with that. =o)

esther on

I think Jessica Simpson is a perfect example of a “dumb blonde”. She was a terrible host, trying to play this bimbo funny chick. I think she is too much into her self and continues to demand attention by chosing ridiculous outfits. Easy on the bleach!

stephannie on

i think jess needs to pack a lifesize mirror with her and look in it before she goes out in public. then she would see that these outfits just don’t fit her like she thinks. jess is a very beautiful, young and talented artist that needs to fire her stylist. and to all the other posts who say she needs to get back with nick, what she needs is to find someone 10 times better looking than nick.

charli on

i heard her hair stylist, Ken Paves, the one who she ALWAAAAAAAYS is with these days dresses her too. Basically, she should fire him and hire a new stylist.

mc on

I think she needs to fire Ken Paves ASAP! She is a beautiful girl when she’s natural, but the fake lips, fake eyelashes, and fake hair are too much. She is fabulous looking without any of that. Now she just looks like she’s headed towards being just a big haired Texas blonde.
The sad thing is, now he’s doing it to Ashlee too.

chicky on

What is with her little shorts outfits lately? They’re not flattering on her in my opinion. Espescially since in many pics she has camel toes issues…hmm…that third picture…a bustier and cargo pants? come on…I think her look says it all there, “what the heck am I wearing?” Oh, and the hair…she should hang out with fellow divorcee Jennifer Aniston. Maybe she’ll get a few new ‘do ideas.

Jenna on

I think Jessica is a very pretty girl, but, here lately, she has been looking overdone and fake. Her lips look too plumped, her hair is pretty, but obvious its extensions, shes always orangie, and the clothes were horrible! I really didnt even like to watch the awards that night because she is so ditzy and i think she acts like that to be cute, but its not! I dont by the whole “blond” act. I think Nick is better off where he is now.

Julie on

I never saw anything she was in…never listened to her music. Until Sunday night all I really knew about her was what was printed. I’d say that for the most part, the gossip I have read appears to be accurate…”fake” “dumb” “over done” “talentless” etc.

nicole on

jess is loosing her sense of overall fashion completly…. somebody help her!

mom2morgan on


Forget her clothes, she needs to lay off the botox. I thought she was so much prettier in her Newlyweds days.
Maybe it was that she looked much better with her Nick on :-)

Elvy on

I remember the days when she wanted to keep everything covered. It’s amazing what a little Hollywood will do to ones values and ego. Don’t get me wrong I’m all for tasteful yet sexy. I just think that’s an interesting transformation not mentioned much.

Liza on

As I watched the Teen Choice Awards, I was overcome with how embarrassed I was for her. From the horribly tasteless plugs for her new album, which, let’s face it, is going to tank, or if it sells anything it all it’ll be bought by 12 year old girls who like bubble gum pop, to her voice which seems to float in and out of this accent that has no specific origin. Most of the time, she looks stunning. We’re not going to lie here. But, even my boyfriend who believes she’s one of the hottest women on the planet said she looked used and abused, and that the outfits added on an extra 10 pounds to the other 15 she’s gained since Dukes of Hazard. The best moment of the entire night was when Nick accepted his award for Best Love Song and said “Awkward!” Yeah…awkward because you looked gorgeous and your ex-wife looked like trash. Nick, keep it up. You’re going to blow her undeserved fame out of the water.

Cassie on

Allright ….. yes jess’s new song is pretty bad, she cant catch a break, but shes still beautiful, i think all of u girls writing nasty things about how she looks are sIMPLY Jealous!!!!!!!!!!!!!GET OVER IT

Dawn on

Normally I think Jessica dresses ok but yes, she too makes mistakes as seen in the photos. I agree with some with the over the top tanning!!

Hannah on

i don’t think she looked that bad

lora on

I would have to say that jess looked just fine, she is a gorgeous young woman. I am a big fan of her….and don’t be jelous of her look….

Kelly on

I love Jessica SOOOOO much she makes anything she wears look good. Although i personally would not wear the clothes doesn’t mean thay dont look good on her.

Lauren on

Okay, so it’s not the best look for her, and yes she’s a little heavier then she used to be…but…these celebrities can’t win for losing! When they loose too much weight, they’re critisized for having alleged eating disorders…then if they’re not rail thin, they’re critisized for being heavy and compared to other stars. Like in Jessica’s circumstances, her newly renovated little sister! Give her a break! All women are victims of emotional eating or lack there of at some point in my opinion! She just walked away from her 1st love and marriage, and she’s constantly being condemned lately for not being better then other people! I think she’s beautiful regardless!

Erin on

She used to have really good style – but lately, it’s been terrible. I agree – the extensions have got to go. I’m not a huge fan of long hair in the first place and her mane just looks out of control. And…she definately had some interesteing makeup moments on the Teen Choice awards – aka hot pink lip stick that looked about as rediculous as it did in the ’80s.

kiks on

Jess is trying to start her own fasion statement. But unfortunily, shes not doing so well. She needs to stick with tight clothing and Less hair. Also she needs to stop trying to cover up her boobs with heavey fabrics. She has too cute of a figure to do all this. Good luck jess.

Calgarygirl on

Honestly I would give my right leg to look half as good as Jessica does!! she is gorgeous…I will agree with the pic of her in the corset (not the best) but overall not really seeing what most of you are seeing!! Jessica is HOT! :)

Norah on

Does anyone notice her face and makeup in pic # 3??? It is not her usual gorgeous face and makeup. The first outfit in pic # 1 is definitley not as bad as the other 2 pics. Jessica is 100 times better than Nick’s girlfriend Vanessa. Why did she dress so horribly??!!! But I do give her credit for hosting. Jess did act really ditsy and fake, but any other person would not have the guts to host when their ex hubbie is sitting right infront of them. I don’t know why should would agree to hosting that award show when her private life and divorce with Nick is SOOO public. Jess is BEAUTIFUL, but musically, she is not talented. Everyone is saying people are jealous when dissing her music. But come on, you would actually listen to “public affair”? Everytime I hear it on the radio, I turn it off. Her cd will probably suck. But Jess is soooo hot and gorgeous, and she seems like a really good person. But her music is bubble gum YUCK.

Audra on

One bad night of clothes. It’s a shame designers make such ugly duds She’s still adorable and Nick sucks!

Nikki on

I love Jessica, she may not alway’s wear the cutest clothes but who doesn’t ever have a bad fashion day, I think every woman can say they have!

Amanda on


Sarah on

It is increasingly obvious that Jess should have never left Nick. It seems she has lost all the style that she ever had. It seems now she is jumping onto the worst dress list. So much for trying to make your ex miss you.

monica on

She looks a hot mess. She will never be the same. She is over doing it. Her hair, make up everything looks awful she needs a stylist. But Nick’s new flame is georgous. Jessica needs to worry more about her imagine instead of Nick’s life. Because if she really cared she would have kept her marriage together.

Erin on

I thought the point of this blog was an opinion about her style, not how trashy she is? Or am I wrong? Although I am personally not a fan of her, I don’t think she should be bashed about her divorce, sister, etc. I agree that she looked “used”. Her skin looks pretty dried out and leathery. But doesn’t everyone in Hollywood? Remember how beautiful she, Kiera Knightley, and Kate Bosworth were when they just arrived on the scene? Now the more popular they get, the more they try to fit in this skinny and tan persona. They all look pretty terrible now. Celebrities barely look like normal people any more.

traci on

Jessica is either waaaaaay over done with her fake smile or a MESS!!! There is no happy medium with her. All these outfits are beyond awful. She needs to fire her stylist and get a brain.

LeLa on

y is she so famous?and for wat?y does she get so much exposure?and for wat?im sick to death with seeing her face everytime i log on to this website or open a magazine.i wish she would just disappear!!FAST!

sabina on

i dont know why everyone is being so mean she is so unbelievably beautful and everyone is just way too jealous. everyone wishes they can look like her and people shouldn’t say mean things like that at all!! that’s mean. if u don’t have anything nice to say, don’t say anything at all!!

jesse on

love the hair. more should cut theirs.

Stephanie on

i love all the outfits. anything looks good on jessica simpson

102394 on

jessica simpson is sooo pretty and she can pull of9af almost anything. so she didn’t dress her best at the teen choice awards. she is going through a lot and she has a little less to worry about. she will come back drop-dead beautiful next year. and i agree with bettyboop (above) her and Nick should get back together. but you never know what will happen with celebrities!!! come on jess, pull it together!!!!!!!!

Mona on

I think she is doing great without Nick. It seems to me HE cheated the whole time especially just jumping out of a divorce into something he is not sure of yet. He hasent been with her long enough to remarry yet. He’s jealous of jess and she can do alot better than a womanizer like him. Her out fits look better than most of the other stars have on . Lets not get into that subject.

Trish on

Keep your head up Jess. Just laugh it off…Your better off without him. And BTW she looks good in everything she wares so don’t hate…

Jen on

Jess looks like a deer caught in the head lights and her eyebrows are a tell tale sign of botox use! This girl does not need botox. What is she thinking? She looks scary.



Brittany on

I love it how everybody keeps saying the people who trash her look are JEALOUS. Good Lord—teenagers should stay off these boards. The topic of this board is “what was she thinking?” and seriously WHAT WAS SHE THINKING? I am not a fan of Jessica Simpson’s but she is a very cute girl who has an amazing body (I personally like her with the extra pounds but by no means is she fat) but these clothes do NOTHING for her. They maker her look even heavier, the tan looks horrible on her, the hair is too much, and the eye make-up—OY! No Jessica! I thought make-up was supposed to look natural? I guess I’ve been doing my make-up wrong for the past 13 years then. Jessica—fire your stylist, get rid of the trashy extensions, quit using spray on tan and I promise you’ll be so hot that Nick will want you back.

Okay that last line was a line. Nick will never take you back but you’d be good enough for a Kevin Federline back-up dancer. Think about it honey.



Jess on

I really like the two black outfits, but not the other 1 i think shes really stunning and i luv her new hair do. Not every1 can look their best all the time (can u)??

night on

Each of these outfits accentuates the fact that she is short…and each one of them also seems to be making her bottom half look kind of large. She is not a large size woman, but these clotes make her look as though she is.

Les Talented on

ewwwww! please stop dressing like that and get a stylist!!!!

Jack on

I don’t really care about any of the bad rap she’s ever gotten during her time in the limelight. I really like her… No… I really like her looks. Really a sexy girl, and maybe that’s about it, no one will hardly get the chance to actually met her, so who should care about anything else.

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