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How Would YOU Wear It? Jessica Simpson

What's with celebs wearing all black these (May) days? I know it's slimming but it can also show a lack of creativity in some cases, as in this one with Jessica Simpson at the 2nd anniversary of the Pussycat Dolls Lounge in Las Vegas. Aren't people supposed to progressively get more and more stylish as the years go by? It seems to me that Jessica has regressed. Although she's never been a style icon per se, I think she used to be much cuter back when she wore girly sweats and Ella Moss dresses.

This outfit is not in the least bit reflective of Jess' youth. Is she trying to compete with the Pussycat Dolls? The boobs-spilling-out-of-the-blazer look is not classy on anyone, especially on a bigger-busted woman like Jess. I don't mind the black pants and round-toe shoes, however. I would have opted for a colorful chiffon halter top and ditched the blazer. How would YOU wear it?


Join The Conversation
crazygirl93 crazygirl93 10 years
Personally I would........Ditch the eye makeup, it looks like she has a black eye, CestLaVie's suggestion of the messy ponytail, a pretty chiffon halter say in a lilac purple colour with beading, keep the trousers, and change the shoes to a silver peep-toe, maybe a silver cluth and a lilac bracelet too...
fashionhore fashionhore 10 years
Jessica lost her stylist Jessica Pastor I think her name was. That is what happened to her. She has been horrible looking ever since then. Some people should not be allowed to dress themselves. But who am I, no? To the question of the hour, I probably would wear the pants with a peep toe pump, say black or a bright color and a black halter with a brooch in the middle of the V. I do like slouchy knit top idea too. But the hair and the eye make-up is not a good look either. Ey, I could go all day!
blondy0806 blondy0806 10 years
let's just not go here...besides the fact that this outfit is relatively unflattering, let's muse as to why on earth she'd wear it to Pure. Honey, though Pure sounds "pure", it's a place to get drunk, down and dirty---how are you gonna do that in a 3 piece????
JKe895 JKe895 10 years
Oh my dear Jessica, you are a hot mess! I love your pants and your jacket but nothing else my dear. FIX IT!!!
crispet1 crispet1 10 years
Woah. Id wear the makeup with a non-trampy getup for starters.
asco00 asco00 10 years
She looks really bad. The fake bake, bad makeup, 3 different fabrics, and those boobs.
GIOVS GIOVS 10 years
she looks bad, wrong outfit
krisua krisua 10 years
UGLY! What's with her these days anyway? She looks BIG to me.
DosThtComInMySiz DosThtComInMySiz 10 years
Ill tell you how i would wear it...... ....take away the pants, jacket, and bust out top. what happened to her???
brazilnut brazilnut 10 years
She looks like an older woman who's still trying to shop in the juniors' department and is just trying way too hard.
lemontwist lemontwist 10 years
Jess can you say "Racoon eyes?". Audra
kungfubunni kungfubunni 10 years
her makeup looks like crap, the whole outfit could maybe work if she wasn't so severe in the face and hair, pull the hair back and back away from the eyeliner. and yeah, i'm sick of her boobs, but to be fair, most guys probably aren't!
kasey009 kasey009 10 years
I normally really love jessica but something is going on here..her coloring is off..its like her skin and hair are the same color almost..i think she needs to un-tan a bit, add some highlights or something, defrizz her hair, lay off the black eye makeup and wear a pretty dress like she used to..she looks too done up
robs1325 robs1325 10 years
One of her problems is that everything else is too dark, the hair, the skin, the makeup... She needs some pink hues on her face or to lighten up her tresses (or cut out some of the tanning gel) in order to freshen up her look. It all seems too contrived. Why is she hiding the bubbly blond that made her so lovable in the first place?
Lala77 Lala77 10 years
I would keep the pants and only the pants, she looks very cheap and shows a leak of imagination in the top of her outfit....u can see hundreds of girls dressed like that for a party it has nothing special about it
Athena1 Athena1 10 years
Tanned vampire. Where is Buffy to slay this beast?
LaLaLaurie06 LaLaLaurie06 10 years
a fun colored top underneath the blazer that accentuates the boobs without being slutty. i would also throw a big sponge at jessica's face. that make-up makes her look like she just got done snorting crack in an overheated sauna.
Glossgirl692 Glossgirl692 10 years
i can not believe jessica would wear something like this. i just refuse to. maybe the pussycat dolls abducted her into their slutty wardrobe and tossed her out in this costume. i hope.
nati nati 10 years
no... and i don't like the make up!
pinupsweetheart pinupsweetheart 10 years
I would have kept the pants, but got rid of the blazer. I would have added a very sexy fitted black shirt with a bit of cleavage showing. Then add some color with shoes and a matching cluch purse.
KerryG KerryG 10 years
I don't mind all black, actually, but from the waist up, she looks just awful. Fashion creativity is not my strong suit, but even a plain black halter top would be better or, as other people have suggested, a white or colorful halter top under the jacket instead of what looks like just a bra. Also, the eye makeup really has to go. Makes her look like a raccoon.
bonchicbongenre bonchicbongenre 10 years
I agree with you Fab, what the hell has happened to Jess?? She was never a style icon but back in the Daisy Dukes days she was very cute. Now shes just...ewwwww
sexyeyes sexyeyes 10 years
I like the look but not on her... She looks like a witch dress all in black :rotfl: _________________________________________________________ Behind every great man, there's a woman rolling her eyes :oy:
rinet05 rinet05 10 years
ok pop those back jess! pls for everyones sake, you could look so much better than this, nt tht i mind all black, bt there's two big things bothering me with this picture
CestLaVie CestLaVie 10 years
Hair pulled back in a "messy" ponytail, keep the jacket but instead of just wearing over a bra or whatever she has going on, pair it with a nude colored halter or cami with a short necklace with a bold pendant, loose the "John Mayer/ Mark A." eye makeup and I like whiplashgirlchild's suggestion of a (un-strappy) peep-toe shoe with a clutch.
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