Jessica Simpson didn't exactly look like she was nursing a broken heart at the airport in Cabo, laughing with her mom and friends all the way. She was also proudly sporting a Dallas Cowboys cap, almost as if she's trying to make a point about the seemingly endless amount of rumors about her breakup with Tony Romo. Even if things with her quarterback are on the rocks, her fresh tan and short little dress should make it easier to patch things up with her man — or land herself a new one.

















D&G
Arizona
Elle Passions
1is tony turning her out? she looks like a cheap hooker
2hahaha wow!
3HUGE shoes!!!
i guess it's just lovely for her that she's supposedly still with tony. if they are happy then that's all that matters right?
4She looks ridiculous! Mouth agape as usual. And why is it such a concern for some people that she lives a minute without a man in her life?
5Tacky shoes.
6stripper shoes!
7she looks stupid she can't dress anymore
8she really does look cheap...short short dresses and super tall stilettos do not equate sexy!!
9WOW jess looks really cute, but the outfit
minus the cowboys cap, GO COWBOYS GO
10She looks cute and happy. I wish I could go to Cabo for a few days.
11cheap shoes..love jess..but that mouth is annoying..sorry.
12YES...I totally agree Woop - why can't she ever close her mouth or smile like a normal person..she is starting to pull the smile that Heidi Montag always does..mouth agape-light-are-on-but-nobody's-home look! UGH!!
And if she is single, so what! She's young, rich and probably desired by a lot of males..the right man will come along...and if he doesn't..again, so what?? I'm sure she'll have tons of fun along the way!
13Can I ask do you people laugh with your mouth closed?
14i know i dont angel blue
15
I like her shoes. She looks more burnt than tan, though
16Jessica....ah, continues to be one of the most pathetic women in hollywood. She is just sooo desperate to let everyone know he's her man, but I thought the press ruined lives and you didn't like to talk about it jess?
17In 3 out of the 7 pics, she has managed to not look stupid because she's laughing without a gaping maw. Oh heck, she manages a gaping maw even when she isn't laughing. hehe
18She does look a little over-tanned
19wow she needs some sunscreen bad
20I agree with hotstuff. First you complain about the press, now you are practically hamming it up for them to make sure they take note that you have a boyfriend. I'm not a big fan of Beyonce but her and Jay Z's approach to their relationship really is the way to go, keep some things close to your heart. You're not in high school anymore, you don't have to wear you QB boyfriend's letterman jacket to let the other girls to stay away. And please please please stop with the stripper shoes!
21Yes your mouth open when you laugh...but is your mouth so wide a mack truck could drive through? I certainly hope not!
She looks a H.A.M.!! Please give it up Jess. You guys are over!
Woop, it seems to me Jess makes a huge deal out of it so everyone else does. She doesn't seem to feel useful with out a man (i.e. the Glamour interview "he brought me back to who I was") Like a vucuum it still works but needs to attachments...
Anytime she gets a man she (or Papa Joe) have to make a HUGe spectacle of it and she becomes a carbon copy of that person.
I bet she doesn't even know what kind of eggs she like!
22she's pregnant and I'm waiting for the announcement with bated breath.
23borrring
24the legs are GORGEOUS!!!
25jaxon - yeah, i agree that her love life being front and center is the Simpsons' doing. It's just sad that this family (mostly joe) is always looking to bank on her personal relationships. It's even more sad that she doesn't seem to mind it (until things aren't going well).
26I think with a longer dress and flip flops she would be really cute.
27She screwed it up, though.
Awe, I love Jess. I'm glad she looks happy but her taste in shoes is just ridiculous.
28Wow, she looks red!! Not a good look.
29What a weird family.
30Her legs are amazing. Dang girl! I wana know her workout routine!!!!
31she looks good. her legs are fit and i love the shoes. She killed the outfit with that hat. and maybe she should do something about that hair. and some lipgloss wouldnt hurt
32She looks like she's with child in that dress. I know they're the style but they're pretty universally unflattering.
33oh sad pathetic Jessica. I bet Tony consented to let her wear the hat in exchange for her to stop stalking him.
34Like the shoes, just not with that moo moo of a dress- and that cap- ugh! Im from Dallas and I wouldnt be caught dead in a dingy cap like that!
35@sou
Good point!! It is so not necessary to try to prove to the media that you are with him by wearing the hat.
It is okay to be without a boyfriend...
36Ugh, her dres is UGLY! But I do love her shoes. I'm short (5ft3in), so I fully support platform heels! And she has gorgeous legs!
37ew hahaha she looks so lurpy what the hell?? hooker shoes, an ass high mu-mu dress, and a baseball cap? and her tan looks like it's turning a nice shade of purple, i feel kind of bad actually.
38Why does everything about this girl annoy me?
39Aw leave her alone, some people have certain features about them that they don't like but can't control. Like me. I have a nice smile, unless it's a BIG smile then you can see my gums, it's really kinda yucky, and I was called every name in the book for it. I couldn't do anything about it short of plastic surgery, and I was NOT going to cut myself up to make OTHER people happy. So she's got a big mouth, maybe that's why Tony stayed with her as long as he did!
40she's got great legs
41She can never keep her mouth closed. Desperate and pathetic for any attention. Continuing on a downward spiral.
42She's gotten really trashy. Great legs though!
43I've always been jealous of her calves!
44All I can do is cringe at the sight of her tranny-hooker shoes!
45her shoes are ugly.
46at the first glimpse, I thought it was Britney.
47um she doesn't look "freshly tanned" she looks incredibly sunburnt which does not send a good message to all the girls copying her. with skin cancer at an all time high i am surprised you would make her tan seem glamourous pop sugar!
48Jessica really needs to learn how to close her mouth. That is NOT cute in a photo. Too many celebs open their mouths like that when they laugh. And that is so darn stupid.
49Close your mouth Jess and wear shoes that aren't so trashy looking and clumpy chunky. You are short. It is okay.
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