Jessica Simpson in New York City

Posted on June 11, 2014

We wouldn’t want to be the types of bitches who go around imposing rules or longing for the good old days of glamorous air travel, but we have to be honest when we say we always appreciate any fellow air traveler who ambitiously opted for an outfit with snaps, zippers and buttons, instead of one held entirely in place by drawstrings. Sure, it’s a high-security age and people shouldn’t be held to some ridiculously outmoded white glove standard for traveling around in a cramped metal tube for hours at a time. But if someone decides to put a tiny bit of effort in? We silently nod in approval.

Having said that…



Jessica-Simpson-JFK-NYC-GOTS-Tom-Lorenzo-Site-TLO (1)Jessica Simpson arrives on a flight at JFK airport in New York City carrying a Givenchy ‘Pandora’ bag.

Jessica-Simpson-JFK-NYC-GOTS-Tom-Lorenzo-Site-TLO (2)

Jessica-Simpson-JFK-NYC-GOTS-Tom-Lorenzo-Site-TLO-(2B)Givenchy Large ‘Pandora’ Bag

Jessica-Simpson-JFK-NYC-GOTS-Tom-Lorenzo-Site-TLO (3)

Jessica-Simpson-JFK-NYC-GOTS-Tom-Lorenzo-Site-TLO (4)

Jessica-Simpson-JFK-NYC-GOTS-Tom-Lorenzo-Site-TLO (5)

This strikes us as a tiny bit impractical for air travel.

It’s also a quite hilariously obvious “DON’T LOOK AT ME I’M A CELEBRITY I SAID DON’T LOOK AT ME” getup. The only way she could make herself easier to spot for the paps is if she hired someone to follow her around with a spotlight on her at all times. Or wore a sequined gown.





Please review our Community Guidelines before posting a comment. Thank you!

  • Ginmaru

    Just imagining the sound of her shoes on a cement floor….”shudders”.

    • Jennica Brocious

      I feel like she might trip though since her toes hang over….that would be a funnier sound 🙂

      • Skippymom1

        I had to scroll back because I missed the “toes hang over.”
        And here I was all verklempt because she was wearing her husband’s silky, patterned boxers on a flight. I thought she just forgot her pants/skirt.
        Nope….now, with your help…I realize…this was **planned**.

    • Introspective

      these clodhoppers deserve to be burnt at the stake.

      in associated humor regarding awkward footwear, does anyone here watch Veep? the finale when Selina’s Louboutins are squeaking as she walks up to make her first POTUS speech?? that bit was priceless…

      • Jecca2244

        we fell off the couch laughing at that VEEP bit. Whole season was hysterical. we laugh so hard we have to rewind. the perfect thing between GOT and bed.

  • Danielle

    When your tassels are tickling your lady garden, maybe it’s time to rethink.

    • OffToSeeHim

      Ok, I’m working “lady garden” into regular conversation.

      • DebbieLovesShoes

        (Me, too)

      • altermyego

        It’s a tough contest between ‘lady garden’ and ‘the fine china’. But since the good china reminds me of Peaches I have to stick with that one. Lady garden is a good alternative.

        Also, does anyone remember the show called Fawlty Towers where John Cleese is the owner of an inn? The Fawlty Towers Inn sign out front always had the letters jumbled. One time instead of saying “Faulty Towers” it said “Flowery Twat”. Now use that in your conversations!

    • Kent Roby

      I want to form a band just so I can name it “Tassle-Tickled Lady Garden”.

      • Ginmaru

        Please let me know when the t-shirts are available. I’d stand in line for one of those!

        • Skippymom1

          Me too. I will bring an extra chair for you.

      • Would make a fine madrigal: “When Thine Tassels are Tickling Thy Lady Garden”

    • Noah


    • mimi

      I love Lady Garden omg.

  • My favorite thing about these photos is the guy photobombing a side-eye

  • RussellH88

    If I were a woman, I’d be worried that I’d be flashing cooch if I sat down in that.

    • Ginmaru

      Not that I think I want to look too closely but she might be wearing shorts.

      • MoHub

        Pretty sure those are shorts although it took me several looks to come to that conclusion. And then: long-sleeved sweater with shorts? And those shoes are beyond fugly.

        • YousmelllikeAnnaWintour

          They look like they are made out of cement.

          • DebbieLovesShoes

            Or silly putty.

    • Cynica

      I found myself actually hoping it was a romper rather than a skirt for that reason.

    • zuzu

      I’d be worried about my skin touching the seat.

      • Who wants to actually feel airplane seats against one’s legs? Maybe she has a sweater in that bag.

      • smh4748

        Yup, she is violating rule #1 of air travel, which is “Always assume the seat fabric is toxic, because it probably is.”

      • DebbieLovesShoes

        Or sitting in the seat AFTER she had sat there and sweated for an entire flight. Ew.

  • schadenfreudelicious

    Nice gams Jess, too bad about the hooves attached to them….

    • LuisaNL

      girlfriend has clearly been working out. a lot! those shoes, I can’t even…

  • Funkykatt

    I want her personal trainer.

  • deelup

    No way I want that much of my leg… err… or any other part of me, touching the seat on an airplane.

  • teensmom99

    Sorry to pull rank but I think some of you just don’t understand how much easier it is to remove platform sandals when you go through the screening . . . NOT!

    • EveEve

      Pre-check = don’t take off your shoes. But I doubt she was there to fly out – more likely there on the pretext of meeting someone. I doubt she’d go to that trouble with hair and makeup and purse placement, unless she intended to be photographed.

    • RunAmuck

      Platforms with TWO buckles!

  • MilaXX

    She’s just happy to have lost her weight from back to back pregnancies. Nevertheless I think this outfit is tacky for anyone not catching a plane, but for sitting on a gross airplane seat? Super ew! Also the shoes are hiddy. The sad thing is, if she was wearing skinny jeans, this would be a cute look.

    • AnaRoW

      You’d be in much more danger from the trays and armrests than from the seats themselves. It’s what your hand touches that’s a concern, not your legs.

      • MilaXX

        I can and do wipe those plastic covered areas with my own sanitizer. However, I’m pretty sure those cloth seats aren’t being wet vac’d between flights which means her bare skin is touch whatever funk & nasties the previous passengers deposited there. That’s a rash waiting to happen.

        • PeaceBang

          Oh, man, I’m getting a little woozy just thinking about that. Ewww.

      • Skippymom1

        Would you want to sit in the seat she occupied while wearing*that* on the flight following her deplaning? I don’t think a Nun’s habit could prevent contamination from whatever she might have left behind. Everyone can wash their hands and use sanitizer, but I certainly don’t want to trust my jeans to ward off the sweaty, sloppy.

  • CakesOnAPlane

    uh…Jess? Do you think we can’t tell that you are sucking in your cheeks like you were storing nourishment for the flight in there? Cause…we can tell.

    • onetinkerbell

      Yeah, the semi-pursed lips are a dead giveaway.

  • MilaXX

    On the other hand, that bag is to die for.

  • EveEve

    And how does one know it was a Givenchy bag? Because her publicist issued the press release about this casual stroll down the concourse (the same one that informed everyone of exactly where and when she’d be on said concourse so the paps could take up their positions.). Gah – so contrived. Having said that, she’s really gotten herself into fine shape, hasn’t she?

    • quiltrx

      I was thinking this is a total bag fail…it’s on the wrong side for the cameras. Someone from Givenchy is probably slapping her right now.

      • EveEve

        Yep – a rookie mistake. Somebody f’d up. Wanna take bets who it was?

  • majorbedhead

    Oh dear god, those shoes are hideous and ridiculous with that outfit, if you can call such a getup an outfit.

  • Rhonda Shore


  • Julie Chase

    This is terrible on all accounts, but man do I envy her thighs.

  • Sarah

    Those shoes are a dead giveaway for either Celeb or Kept Woman. Also, the tassels on her sweater(?) first appeared to be emerging FROM the shorts, which gave me all kinds of confusion re: the need for ladyjunk bell pulls.

    • Kayceed

      Bell pulls for one’s nether regions! I am laughing pretty hard over here…

  • OffToSeeHim

    Well it’s probably easier if you’ve got your own plane.

  • Kent Roby

    If she’s jetting off to see her gynecologist (or planning to join the Mile High Club) I’ll give her bonus points for time-saving practicality.

  • ojosazules

    I kinda don’t mind if Jessica Simpson moves through airports looking like this. I bet it makes a shitty day of traveling a little more fun to look up and see this madness.
    Are those bloomers?

  • OffToSeeHim

    Plus she gets a pass no matter what from me right now, because she worked so hard to lose that weight and she just looks SMOKIN’ hot. Good for you sister, WORK that short skirt and CFM heels!

  • shirab

    My kids and I sometimes while away the hours before a flight by looking for super-ridiculous airport footwear. We’ve seen some crazy choices, but those shoes might be the worst, aesthetically and ergonomically.

    • kimmeister

      Ah, people watching. Such an entertaining pastime!

      • Kayceed

        I once flew to Vegas the same weekend as the NBA All Star game (not that I knew at the time) and WOW the ladies on the plane were wearing some ambitious footwear.

  • FrauKrissie

    I can’t help staring at the bruises on her knees.

    • somebody blonde

      I don’t think both her knees are necessarily bruised. Some of us pasty folks just have knees that get excessive blood flow when we’re exerting ourselves, which turns them a different color and makes them look kind of bruised, especially in pictures. The one on her inner right knee is probably an actual bruise though.

  • numenah

    Even worse hair, if that’s possible, than Gwyneth’s.

    • evave2

      The first shot had her hair looking green to me; I figured it was just the light she was in because the others look appropriately blond.

      But the shoes! Not so much the color but I approve of whoever said hooves.

      Ah, flying: I remember when one dressed for the air travel. Now I just want to be comfy and have my sudoku book close at hand. And my rosary in the top part of my purse.

      Susan6 (below): other than the greenish tint to her hair and the weird pinkish shoes, NEXT on my list was the idea of her skin STICKING to her plane seat. YUCK.

  • susan6

    I hope that huge bag has a pair of pants in it, because bare legs on airplane seat = gross. As for the legs….well done to her and her personal trainer.

    • kimmeister

      Well, if Sheldon Cooper can have “bus pants,” then Jessica here can have “plane pants”!

  • marlie

    First, those shoes look like a pain in the ass to walk in on the best of days, much less one in which you’re schlepping through the airport. Second, and it’s been said before, do you really want your bare ass on a public airplane seat? GROSS. Third, her hair is a (not so) lovely shade of yellow-green. Girlfriend needs to stay out of the pool and get her hair color corrected, stat.

  • Anna

    I like the bag. That’s about it.

    • kimmeister

      I like the shades.

      • Anna

        I think may need them to shield my eyes from the eyesore that makes up the rest of the outfit.

  • Bad Idea Jeans

    I’ll take the bag. She can keep all the rest of it. The bag deserves better.

  • bhl_1123

    Kudos to Jess for working so hard on the figure–your legs look killer! The outfit (especially the shoes)–YIKES!! But most, importantly–>Girl, what is up with those knees?!! Did you crawl halfway through the airport because you couldn’t hoof it in those horrible shoes?

  • yethica

    I think the neon yellow, dirty, stringy hair is what makes it for me…

    • MoHub

      Her hair is making me cry.

  • HomeOfficeGirl

    What’s the female equivalent of a douche bag?

    • demidaemon

      That’s a really good question. I have no idea.

  • JP

    Those shoes must be a bitch to take off for the security line.

  • Carleenml

    It looks like her lips are physically pulling the rest of her around the airport.

  • somebody blonde

    Wow, she’s definitely lost weight since the last time I saw a picture of her. I actually didn’t recognize her because her face looks so much thinner. She looks good either way, though a miniskirt with platform heels is definitely a bit much for the airport. And I say this as a person who has worn 4-inch heeled boots in the airport because they were too bulky to fit in my carry-on. It’s really the combo that seems so misguided.

  • TLJezebel

    Pee-colored hair in desperate need of conditioner.

  • LadyVimes

    How are those tassels not getting stuck between her legs? Anytime I wear a scarf that kind of length, It ends up stuck so attractively in between my legs when I walk.

  • Hair doesn’t really come in yellow like that, right? First Goop and now J-Simp? Why do they think this color is good for anything but highlighting text?

  • smh4748

    Girl loves her Restylane, doesn’t she? Wow.

    And Jess, that is not your hair color. Or anyone’s.

  • mimi

    I hate that subtle duck-face she’s got going.

    • CakesOnAPlane

      It’s not subtle. Picture 3 looks like she is literally chewing on the insides of her cheeks.

  • decormaven

    The only reason she should be wearing those shoes is if they are from her own footwear line. Totally inappropriate, otherwise.

  • V No Privacy

    It’s the shoes that ruin/make it. If she was in sensible sandals, she’d be more believable. (even better if she pulled her hair up/back and switched out of the glam glasses).

  • OhSheila

    She said, “you WILL look at my muscular thighmeats!”

  • Andrea Lentz

    the shoes are ridic but otherwise i think she looks cute and comfy. And her legs…damn. maybe if mine looked like I would wear heels to the airport too.

    • Nancer

      Totally agree!

  • frannyprof

    The duckface + platforms + sunglasses + skirt up to *there* = desperate celebrity begging for attention. She bugs me. Not in the way Gwyneth Paltrow bugs me. I can (grudgiingly) admit that GooP is a talented actress. Ms. Simpson, here, is bereft of talent. Other than making shoes for the masses (and, making a profit in the process, I know), there is nothing to this gal.

  • boweryboy

    Get rid of the stripper pumps, replace them with some simple black flats, pull her hair back in a loose ponytail, and I would be in love with this look. As it is, I’m more in love with the serious bearded shorts wearing guy behind her. Woof!

  • She looks both like a set of badly mismatched Fashion Plates, and a celebrity impersonator of herself.

  • Bernadette

    This is a hot mess, obvie, but Damn, girl got some gams!

  • MarissaLG

    I just imagine her having to sit there and buckle TWO BUCKLES PER SHOE after going through security. That or having her assistant do it. Yuck.

  • miscorrections

    Giiiirl, toning is for more than just your legs. Hire a kind professional to sort out that mess of plastic horse chow on your head.

  • uprightcitizen

    I guess she’s worked really hard to get her Daisy Duke body back, but there has to be a better way to show off that effort than walking through an airport looking like you just need to peel off your sweater to get back to your pole-dancing shift.

  • melanie0866

    She could crack walnuts with those legs. Damn.

  • Jennifer Bober

    Okay, seriously? These are the shoes you wear for walking around the airport? I’ve done major travel and there is no way I would wear heels, never mind THOSE heels in the airport.

    The whole thing screams “I’ve lost the baby weight bitches, so leave me the hell alone.”

  • crash1212

    Naked legs on airplane seat. NOPE.

  • ashtangajunkie

    Needs to work on her bitchface. It’s too forced. See: Jones, January for a how-to.

  • seventeenwest

    “In the event of a water landing, we will catch fish to survive with my pool cover up, y’all.”

  • Jennifer McGuire

    All I can think is that i personally would FREEZE to death on the plane with bare legs. Gah. Also, please no with the band-aid colored platforms.

  • paintedfish

    Gawd, thems some stripper shoes.

  • AMartel

    Impressive tone and definition she’s got going there. Put some bass in your walk!

  • SierraDelta

    Are she and Gwyneth sharing the same box of lemon Jello for their hair color?

  • Jecca2244

    those legs. Wow. it pains me that no matter how hard i work at the gym i would probably need a trainer and 3 hours a day to make them happen.

    • marlie

      I’d bet that Jessica *does* have a trainer and does at least 3 hours/day at the gym.

  • Joanne Abrams

    ouch, what’s with the bruising around her knees?

  • Lily

    Those shoes scream Debbie Does DFW.

  • PeaceBang

    Is she giving duck face or is that an unfortunate side effect of a cosmetic enhancement?

  • Ankle straps in the security line. We frequent flyers hate her.

    • colleenjanel

      I agree! Though I’m betting she travels enough to qualify for PreCheck and doesn’t have to take her shoes off.

  • warontara

    The shoes are a horrible decision, but I’ve been that girl before (getting that last pound out of my checked bags), so I won’t judge…much. But those shorts?!

  • cat772

    Totally cute with a pair of flats or flip flops. Unfortunately that’s not what she’s wearing.

  • Mothra

    My goodness she looks toned. Even her lips! Although I am questioning the oddly green blond hair.

  • J. Preposterice

    daaaaaammnnnnn girl tell me what your leg workout is these days

    • poggi

      It may in fact be those shoes. Fit Flops my ass, bring on the sky high clodhopper heels!

  • demidaemon


  • Wink

    Her hair color is ‘chicken fat yellow.’ Ask for it at your salon.

  • Emily S

    She has THE WORST TASTE IN SHOES. I know she has a multi-million dollar empire, but there’s absolutely no taste there. Awful.

  • nancymae

    Those shoes! And those toes?!! And this woman has a relatively cute shoe line. As my friend says, “you think you looking cute but you really looking curious.”

  • d4divine

    She kinda looks like a tired hooker, but her legs are banging!

    • Skippymom1

      The minus and plus of Walking the Streets.

  • FibonacciSequins

    Short shorts for sitting in an airplane seat? Ew. I bet she also takes those shoes off the minute she sits down and puts her bare feet up on the arm rest of the seats in front of her. But the shorts and shoes got the job done, since we’re looking at her and talking about her.

  • Sif

    looks like something that Willam Belli would wear.

  • Esz

    She’s thin again??

    Those shoes are dirty.

  • The sweater and sun glasses are really cute. Everything below that is pretty amusing, but I don’t think that’s what she was going for.

  • largishbearishAtlish

    Are those lips new? or a fresh injection? and not to nit pic, what color is that hair?

  • Gatto Nero

    Those shoes.

  • Sabin

    No really, that’s a drag queen…right?

  • ms_kat

    As the fug girls often say: CONSIDER PANTS.

  • Lizzy

    Well… she’s really got her pre-baby body back. The tassels. .. how would that not bug?

  • altermyego

    It’s funny that you write “look at me” because it seems like all the guys in these pictures aren’t noticing her at all. Even if they didn’t know she’s a celebrity you’d think a pretty blond like her would at least be getting some glances. Maybe they sat next to her on the plane and she wouldn’t shut up the entire trip.
    What a fantastic looking travel bag. Looks like it’s practical too.

  • carnush

    Yep, I always wear my six-inch platform heels when I fly. Helps me reach the overhead bin.

  • Bower Bird

    I really love Jessica SImpson and think that she has a great attitude. That said, I can handle the shirt, the bag, the heels.

    However, the shorts are SO Richard Simmons ca. his 1979 General Hospital days of exercise class at the Campus Disco.

  • Skippymom1

    My hair turned that color after ever season of swimming in a chlorinated pool.
    J. Simp – get you a salt filter for you swimmin’ hole and save the tresses.

  • Juniper

    Why is no one taking about her legs? Her amazing strong, when-did-she-get-those-legs, legs?! I don’t even see the rest of what’s going on in these photos. (Well, that’s not entirely true. Her shoes and hair did sear my eyeballs just a bit.)

  • Terri Terri

    She’s doing that Erica Kane thing where the lipstick goes way beyond the lips.

  • Candigirl1968

    I guess she is in no danger of missing her flight because I can’t see running to the gate in those way too tall, way too small shoes.

  • webslice33

    those are killer legs!!

  • hillmad

    Those shoes must be as treacherous to walk in as they seem; look at the bruises on her legs and, especially her knees! OUCH!

  • heartbot

    Those are my mom’s swimsuit bottoms from 1993.