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Jessica Simpson @ Costume Institute 2007

Jessica Simpson @ Costume Institute 2007

Jessica Simpson in Roberto Cavalli Fall 2007.

To the right, Dutch supermodel Lara Stone.

For 35+ pictures of Jessica and beau John Mayer, CLICK HERE!

Who wears it best — JESSICA SIMPSON or THE RUNWAY MODEL?

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Miguel Villagran/Getty

119 Comments

# 1
Shimmeringdew @ 05/07/2007 at 11:00 pm

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They both wear it well but yes i would have to say Jessica sure does “fill” it out a lot better…

# 2

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Model.. Jess looks ok..JESS looks different somehow cant put my finger on it…

# 3
sunshineday @ 05/07/2007 at 11:07 pm

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jessica looks kinda like a pornstar here…model.

# 4
Marie Jane @ 05/07/2007 at 11:09 pm

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The model - Don’t get me wrong, I love Jess - but the dress, the make up, the hair, the super enhanced boobs make her seem like an expensive street walker.

# 5
[ Fug Face [You] ] @ 05/07/2007 at 11:11 pm

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Jessica looks like a Fcuking-Hooker, the only reason she wins this is because the model looks disgusting.

# 6
KrungKrung @ 05/07/2007 at 11:13 pm

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ohmigod, Jessica’s t*ts are really humongous as in humongous

# 7

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The model. Sometimes Jessica gets it so wrong…she looks like a man in drag here.

# 8

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whats wrong with Jessica??? too much tan too much make up!!! she used much cuter.

# 9

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jess looks horrible!

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Oh dear, Jessica what the hell is going on inside that bird brain of yours?

Shoes4life @ 05/07/2007 at 11:21 pm

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Ewww for Jessica! I guess she’s bringing ****** back.

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what the f*ck is wrong with her face?

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you’re right sun, she’s like a pornstar

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The model looks a million times better, what’s wrong with her boobs, they look Pamela Anderson big. With her fake tan, those red lips, and those gigantic globes about to pop out she really looks like a hooker in a nice dress :S cover them Jess, please…

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JESSICA HAS:

NO WAIST

NO NECK

AN AIR OF DESPERATION AS THICK AS THAT PATTERN OF SPARKLE MAKES HER HIPS LOOK

SHE IS A TRANSVESTITE ROCKETTE

GOODBYE!

Shoes4life @ 05/07/2007 at 11:30 pm

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Do Bucky Beaver ever close her freaking mouth for photos. It is not sexy, never has been.

[ Fug Face [You] ] @ 05/07/2007 at 11:32 pm

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Jessica got that tan-in-a-can better known as the Aguilera Oompa Loompa special, not to mention two pounds of make-up. Bozo would be proud.

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a hot damn mess. she had the sleaziest look of the night, by far. she’s trying way too hard to be sexy, the real sexy ones do it with more ease.

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Both women are amazing and both look good

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Jesus, can she ever wear some form of clothing that covers up her boobs….

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Side boobage AND a down-to-your-navel-V-line-massive-cleavage-bearing front, does not a formal gown make. Jessica needs to dress her age. She looks like a ****** teenager on PROM NIGHT!

Faithinher @ 05/07/2007 at 11:55 pm

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18
tanique33 Says:

May 7th, 2007 at 11:36 pm - flag comment
a hot damn mess. she had the sleaziest look of the night, by far. she’s trying way too hard to be sexy, the real sexy ones do it with more ease.
*****************************************************************
So true! Definitely a mess.

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jess looks cheap and ******

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No one does trashy like Cavalli

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OMG.. Chestica looks like a tranny. Like a cheap, cheesy and desperate tranny.

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Jessica Simpson is an embarrassment!!! She looked horrible. She needs to stop with the plastic surgery. That body is totally plastic or steriods or something!!! She looks like a huge inflatable sex toy! Her 15 minutes are up. I’d hate for her to end up being the next Pamela Anderson…or worse! She certainly doesn’t look like she belongs at this event. Terrible.

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I do believe the Jessica looks like a human Jessica Rabbit in these photos.

But, terrible dress to wear to The Costume Institute. The fashion event of the year and her stylist **** it up by dressing her like a Las Vegas tart. Can we say arriviste?

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What the hell is wrong with her!! OH MY GOD!! In the fourth picture she seriously looks like a MAN in the face, but the flotation devices in the front make you think she’s a woman.. I’m so confused..

I have big boobs, like Jessica.. If I tried on that dress and my boobs are sticking out on the side, I would put the dress away and say, “sorry, that dress just doesn’t fit me right’.. That dress has enough fabric to cover her nipples and not much else.. I mean, her boobs are squashed in the front, hanging out the sides.. Its just a disaster.. Whoever convinced her to wear that thing needs to be shot.. Its just so so so wrong.. Everyone else looks so classy and she just looks trashy.. EWWWW.. Horrible.. I gotta go wash my eyes with soap.. AAAAAAAAAAAARRRRRRRRGGGGGGGGGHHHHHHHHH!!!!!!!!!

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WOW….Jessica became SOOOOO t*ashy. What is going on with her. It looks very sick. I was never a huge Jessica fan, but if I was….I wouldn’t be anymore after this

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Model. Jessica looks like she be turning tricks somewhere not walking up the steps to the MET.

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Lara Stone, the model, looks exquisite… You can’t get much cheaper looking than Jessica Simpson; she literally destroys the dress.

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the model wears it heaps better!!!

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Someone is looking for attention and in a very wrong way. I agree she does look like a trashy porn star who tries TOO HARD too look sexy. She has nothing to offer so might as well let those girls out!

Sweet Swede @ 05/08/2007 at 1:02 am

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The dress is very nice, but it looks beyond awfull on Jessica.

lurker opinion @ 05/08/2007 at 1:10 am

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What has happen to her? Did she have a boob job? Not that she needed one but something other than her hair color has changed.

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The model looks like hell too. The model’s too pale and Jessica’s too tan. And her boobs are too big for the dress. She also doesn’t know how to stand, she always sticks her chest out and she needs to learn to pose better. I don’t know who’s training her, but she should get better management.

Also, she makes faces and that’s why she looks crappy in pics sometimes. She always looks best when there’s just a natural shot of her. All in all she’s a hot mess.

John looks real good though. Go John.

Ace Tomato @ 05/08/2007 at 1:15 am

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The dress is supposed to look like a 1930’s silver screen goddess gown. But J.S. is too short and busty for the gown. I know why she wore it - I wish I could pull that gown off as well, but I have a similar build. Every time I go for sleek and shimmery sheaths it never quite gets where it should be.

I doubt she was going for porn star.

Somewhere she found a mirror that tricked her into thinking she looks tall and willowy. Poor thing. The dress was made for Rita Hayworth.

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What is wrong with Jess lately? She looks much better with blonde, and Lohan looks 100% better with brunette. Just like everyone else here, I totally do not dig Jessica’s look. Heavy (and so out-of-date) brown makeup and umm…, too revealing. She needs to understand that trash look doesn’t impress anyone. She was (kind of) sweet and cute on Newlyweds, but now she’s like, a totally different person. Now I’m starting to feel sorry for her.

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Twinkle. I thought the same thing. JESSICA RABBIT!! She looks just like her. Ewww.
She has become so gross. When she first came on the scene with her nose with a bump—I thought how beautiful she was. Now, she looks like a tranny freak. She ruint her look—that’s for sure.
Hey, check out my friend’s youtube. It’s celeb comedy and is hilarious.
http://www.youtube.com/peron75

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Jessica looks cheap and trashy.

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what is wrong with j’s boobz? omg there is something WRONG with those!

they are making me nervous.

stop STARING at me, hideous freak boobs!

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I have to say that this is SICKENING! She looks like a 45 year old tranny in this dress. The face, hair and tan are just too much!! She really went off in this one!

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the runway model. period. :-D

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The model. She’s elegant and beautiful.

Jessica looks like a tranny pornstar.

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You know, I never thought I’d say this, but Jessica needs to go back to blonde. She’s trying to play around with her look, which is great, she’s in her 20’s nothing wrong with it, but the blond did her features more justice. The dark hair makes her look older and even cheaper actually. The blond made her look more carefree and breezy.

But John Mayer is looking the hotness, I have to keep saying it. Damn.

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Why? Oh why, John? I love you music and you but why Jessica? You could do SO much better…..I miss the sensible John!

MerDer4ever @ 05/08/2007 at 2:31 am

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too much tan… too much make up. that lipstick has to go. what’s with her lips??? too much boobs.

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what happened to fresh jessica …….sigh

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28
Emme Says:

May 8th, 2007 at 12:22 am

I second that! What was she thinking??..but this IS Jessica Simpson, sooo she wasn’t thinking. I CANNOT believe her dad was a pastor.

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The model of course. Jessica looks like a pornstar in this dress. It’s way too small for her breasts! What was she thinking?

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the blonde hair suited her MUCH better!

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Ok, yes, the dress is definitely to skimpy for her on top, but I quite like her hair and think she looks rather distractingly sexy… but, maybe I’m just distracted by her amazing breasts (kind of hard to avoid)!

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too much plastic surgery that’s what’s going on… with both of the simpsons :p

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Whats wrong with her FACE????

Anybody else who sees it? It looks like she has implants there or botox. just very strange. plus the awful make-up. all in all she never looked that dumb.

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jessica is a pretty girl why is she always loading on a whole makeup counter? this whole fake tan looks bad and the makeup makes her look like a man. she looks so much prettier natural :) she doesnt have to show her boobs to look sexy either. John looks hot!

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The women’s expression in the second to last picture is priceless!

Jessica looks horrible. Something is definitely wrong with her face and why does she keep making those expressions. The last picture is awful, her arms and shoulders are so manly.

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Gosh, Jessica is horrible! She looks like a hooker.

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oh my god…. I think she confused the place to go….. what a pity of dress.. and girl

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Jessica - trying for classy but failing so bad.

MissCarla @ 05/08/2007 at 7:16 am

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Maybe she’s playing up a different angle to win John’s heart. I’m still not convinced that he’s that into her.

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Why is she turning into a black woman? How much tanning juice does one person need to smear on their body? She looks rediculouse. As far as the dress, the model is MUCH better. Jessica looks like a **** - very trashy. Having your breasts pouring out of a skimpy dress at an event like this is A BIG NO-NO. It’s like she doesn’t understand what it means to be and look sophisticated and classy.

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Not crazy about the tan or the dark hair. To me she was much cuter when she left things to the imagination instead of throwing them out there for everyone to see.

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The model. I think this dress is completely inappropriate for Jess to wear to this glamorous event given her “talents”. She should have gone for something a little more modest.

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Anna Nicole LIVES!

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Why would someone as young as J-Simp want to look like a tough old broad, esp. among this guest list on this occasion?!?! Must share the evening’s Tranny Award, though, with poor ol’ Molly Sims …

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Jessica looks like pornstar….. she wan’ts to be sexy

Mediterranean @ 05/08/2007 at 9:10 am

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Are her breasts real? I am not joking at all. Are they real?

[ Fug Face [You] ] @ 05/08/2007 at 9:21 am

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wow.. Jessica finally got more than 40 comments, and it only took her dressing like a dirty hooker to do it. Congratulations Chest, keep up the good work loser.

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I can’t take people who are mad at John Mayer for dating someone they don’t. People act like they own celebs and they can’t have a life that doesn’t fit in the box fans have created for them.

John Mayers entitled to like, love, date anyone he sees fit. It’s just tiresome all the time with all the, he’s not that into her. He’s dating her! I mean, really dating her, he is that into her. She hasn’t killed anyone. She needs better fashion sense that’s all. That’s not a crime.

And I don’t think she’s that stupid. It’s not like anyone on here is walking brillance. And when did that become a requirement to be loved. They might not grow old together, but dammit if you can’t sample around and have some fun.

I just had to rant about that. Sorry.

shut up haters @ 05/08/2007 at 9:28 am

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Jessica, looks great. shut up you flat chested haters

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she looks AWFUL-too trashy for such an event. i think she looks just like jessica rabbit here too. oh and since when did john mayer get hot?

Mediterranean @ 05/08/2007 at 9:49 am

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If her breasts are real, they look very beautiful. Her face looked much nicer before. I prefer her blond.

Alexandria @ 05/08/2007 at 9:53 am

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OKay I know Jessica’s boobs are big but seriously, I swear they are BIGGER than usual. She needs to control those puppies, she looks so trashy. She looks so illproportioned. IS THAT THE WORD? Whatever.

Model looks 1000x better

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Ha ha ha, now that you guys said it, she does look like a drag in those pics. How did she do that ? she has like the sweetest face in the biz, how did she mess up so much and look like a drag queen now?

I guess its the over-the-top red lips. But I’m sure with different light the make up might look better.

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to much boob, the model looks better

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Poor Jess, she looks so desperate. She looks hideous and way too masculine. She’s too short and buff.

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she looks very manly

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i mean Jessica of course

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her boobs look bigger has she got a boob job??

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Jessica looks like a drag queen here.
The model looks pretty.
John Mayer looks hot with shorter hair.

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Awful on Jessica but perfect for the model. Jessica seems to be trying so hard to look a high class hooker.

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her boobs are outta controllll!!!!!!

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John doesn’t look comfortable in the pictures. Trouble in paradise? Jessica trying hard to be sexy, Meyer feels he’s gone so trashy with her looks or… well….

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What’s up with the boobs? She looks like a porn star reject!

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What the h*ll happened to her? She used to be pretty on the cusp of beautiful. Now ‘Pam Anderson’ boobs, Bozo makeup, hooker clothes. Stop trying so hard jeez…. Sexy??? NOT

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Model hands down..Jessica looks like cheap trash.

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Jessica Simpson looks like a drag queen from tailand!!! please dun even try to be sexy u got it all wrong!!! FUGLY!!!!!

[ Fug Face [You] ] @ 05/08/2007 at 12:52 pm

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“cheap trash” Lol there’s expensive trash?

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jessica for sure…those boobs…:P

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It is her lips, her lipstick is several inches above her actual lip (upper) she is trying to hard to push she lips and be sexy instead she just looks funny and like a street adult film start trying to go main stream. Boobs look great tho .. WOW

SweetyKat @ 05/08/2007 at 1:52 pm

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Is is me, or has this girl had a boob job?

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wow…she really CAN get trashier…

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Model. Jessica wins the noise….negative publicity!

[ Fug Face [You] ] @ 05/08/2007 at 2:17 pm

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Cant people tell real booobs from the fake ones?!?

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Why is she orange?

yuckyuckyuck @ 05/08/2007 at 3:03 pm

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the model. the dress on the model shows off her curves. the dress on jessica looks like it’s smashing and barely able to support her huge boobies. not a flattering look. there are plenty of styles suited for big boobs, this is not one of them.

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JESSICA LOOKS LIKE A DRAG…STOP PAYING KEN PAVES TO TELL YOU LOOK GOOD…OBVIOUSLY HE’S THE ONLY ONE WHO THINKS THAT!!!

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cannot believe this trash got invited to that soiree
you know this gathering being what it was, the anna wintours of the world were snickering and laughing at her all evening… does she not know that there is no place for bazoonkas like hers in haute couture, esp. paraded to the point of desperation like that - good lawd!

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Stop with the damn pouts! She is trying way too hard to try to look sexy. I miss Jessica the way she was when she was with Nick: natural and herself. She wasn’t trying very hard back then, yet she always looked sexy and great, IMO. I loathe post-Nick Jessica.

I’ll sum up what I read on another site, which I think hits the nail on the head:

Jess left Nick because she thought she was hot and that every guy wants her. Of course, she only found out that nobody really wants her and that she’s not all that. Her album failed and she couldn’t get a boyfriend for months (when she does get one he’s fugly and weird). Nick, meanwhile, went on to release a good-selling album and met a wonderful girl, Vanessa, whom he has been wth for months and they are still going strong.

Tough luck, Jess. You made a mstake. BIG time.

latin_kaos @ 05/08/2007 at 3:24 pm

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Jessica looks every day more and more like Jessica RABIT…lmao

SF Stylist @ 05/08/2007 at 3:27 pm

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The Model Looks much Better in that Dress.

The dress is too long for Jessica Simpson and the waist doesn’t hit the right spot on her curvy figure. Also, I agree with all the posters who say she looks like a pornstar in that dress. The costume institute ball is one of the most elegant high fashion events and she showed up looking like a pornstar.

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Listen Me Jess …

NO MoRe BOOBS!!
Stop that …

Aucune Classe maintenant…

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Oh no, how embarrassing… Simpson has no class. The way she shows her boobs aren’t even sexy, but grotesque.

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Jessica looks nasty.
She’s fake.

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John looks HOT. Jess is now the FUG half of that relationship!

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It’s really sad that Kev Paves is there. Can’t Jessica function without him? He is behind her in one of the last 5 pictures. There is something not quite right with that snake Ken, I can’t put my finger on it. I agree John looks hot - for once.

Rocky (female) @ 05/08/2007 at 4:43 pm

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When Jessica Simpson did the reality show with Nick Lache, she was, effortlessly,
genuinely cute and sexy. After the show, her “success” went straight to her boobs!

Lately, she looks like she is auditioning for a remake of “Whatever Happened to Baby Jane”. It’s sad that someone so young can become a has been so quickly.

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lets talk about john !
he looks smokin’ hot… LOVE the hair!!!
gorgeous face, eyes, lips, and skin!

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wow jess seriously needs to stop with the lip injections! i miss the good old days with a light tan/less makeup.

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Well are they real or fake? Can we blame this new look of Mayer?

Mondo Bongo @ 05/08/2007 at 9:50 pm

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~ :( ~

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I think Jessica Simpson looks soooooo much better now that she’s put on a bit of weight! she looks great! you go girl!!!

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Awful dress, and neigther of them looks good in it. Yuk!!

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The model. Jessica makes the dress look really ******.

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why does jess try too hard to look sexy?

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Jessica, honey, when will you learn less is more?!!!!!!!!!!!!!!!!! That is not the dress to be wearing when your chest is that big. It doesn’t fit. And what is with all the fake tan? I’m not a huge fan of yours but you’re a pretty lady. Why do you do this to yourself?!!! Why do you insist on looking this trashy?!!!!! Sort it out!!!!!!!

On a brighter note, it looks like John Mayer finally bathed…….

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her boobs are too big for that dress. but the real story here is john! did he finally let ken paves give him a hair cut? he cleans up real nice! i think they spend all there time ******** and that’s why she walks around looking so trampy now. so much for her good christian values. ha!

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For girls that used to sing in church, and a father who was a minister, Joe took them to Hollywood to make stars(and money) out of them, but in my opinion he only made ****’s out of them! Maybe God won’t judge him too harshly!!!!!!!!

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