Lindsay Lohan in Ashish on the “Late Show With David Letterman”

Posted on April 08, 2014

Oh, GOD. Really, Lindsay?


Lindsay Lohan after taping an episode for “Late Show With David Letterman” in New York in a vintage Ashish dress paired with Christian Louboutin booties.

What the hell are we looking at here? How does she manage to look both her own age and 30 years older than it at the same time? We assume she doesn’t have a stylist, since she’s both legendarily difficult to work with and hasn’t been anywhere near A-list status for close to a decade.  So, fine. She’s a gal without guidance – in more ways than one. But even so, you’ve got to have some awfully shitty style instincts to put a look like this together. This dress – which could’ve looked amazing on her – is not a dress that calls for thigh-high hosiery, booties, a white sack coat and a black fedora. It’s all way too much. To be honest, what this look calls for is a pair of black or white or silver shoes – and that’s IT. We’re always lamenting the ladystars who don’t style their looks enough, but Lindsay goes in the opposite direction and drastically over-styles everything.

We are SO ready for the “Frozen” braid trend to die, but we suspect it’ll have a distressingly long shelf life.



[Photo Credit: AO Images/PacificCoastNews]

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  • hillmad

    Grey Gardens realness, that’s all I can see.

    • Jessica Freeman

      She and Dina could do quite the remake.

      • decormaven

        Don’t give them any ideas.

    • traceyishere

      I’m sure there is cat hair on everything she owns.

      • kimmeister

        Any pet who lives with her would surely have to be rescued.

  • Kate Andrews

    OVER IT! She’s so, so ridiculous, and Oprah should never have put her on TV.

    • demidaemon

      The only good thing about it is seeing Oprah get mad and layeth the smackdown. With bleeping.

  • Alicia

    Those booties with some skinny black pants and a sparkly top would be good.

    • Mrs. Julien

      Those boots are gorgeous. Just not for this outfit.

  • HomeOfficeGirl


    • lexilexi

      YES! And THOSE LIPS!

    • Tracy M

      What happened to her face?! She’s both tight and bloated looking. Egad… just stop!

  • geans

    My first reaction was “Liza” but then I was like wait, no, Liza is cooler than this.

    • KateShouldBeWorking

      I thought Liza and Stevie Nicks. Like peanut butter and cheese: good on their own but terrible together.

    • prisma

      I thought Liza also.

    • Chase

      Yes, Liza! That’s exactly it.

    • Clash D

      Liza it is.

    • FrigidDiva

      That’s the first thought that popped into my head when I saw the first picture.

  • RussellH88

    I think she saw David Hasselhoff performing on the Berlin Wall and had a flash of misguided inspiration.

  • KinoEye

    Michael Jackson in the later, crazier years. Egads.

  • MilaXX

    I’ve been reading the recaps of her show over at FUG girls. Apparently shitty instincts is her MO. She’d have to be a style savant in order to be able to dress herself. That’s a really cute dress. Lose the hat and the thigh high socks. I’ll give her the boots and coat due to weather but the hair has to go. The she could be at least passable.

    • Jessica Freeman

      …and also know she is broke and can’t afford a stylist. But given the behavior covered on the show she wouldn’t listen anyways….

      • Alicia

        But how can she afford all the life coaches and assistants and NOT a stylist?

        • Jessica Freeman


        • shopgirl716

          I think either the production company or Mother Oprah is covering the life coaches and an assistant. I watched an episode and it was painful. Bless her heart.

          • caroline

            Maybe after this Mother Oprah will spot her a stylist, too. Bless her heart is right.

      • MartyBellerMask

        Well. Even with money, she’s been known to blow off her bills.

  • Bonnie B

    Sorry, fav uncles. I LOVE my braids and rock them daily :-)

    • random_poster

      I love the look of a well-styled braid. I’m not a fan of what she’s done with it here.

      • Trent

        I think the problem is more her thirsty weave masquerading as an overlong braid.

  • Anna

    Personally, I can’t think of anything better to go with my favourite lab coat and sequined Ashish piano border dress than the Witch-king of Angmar’s boots.

    • zuzu

      Now, if she’d borrowed his helmet, we’d be in business!

      • Anna

        The helmet would actually improve the look!

    • KinoEye

      She missed an opportunity to really make an entrance by arriving on one of those bird things the Nazgul rode — Google tells me they’re called “fell beasts.”

      • Anna

        Ha, yes! That’s what this look needed besides the Witch-king styling: more “fell beasts.”

        And I certainly shriek like the Nazgul whenever I see her 😉

        • leilah

          Glancing through, I totally thought I saw “fell breasts” and thought, “yeah, that would be them … “

          • demidaemon

            That sounds…very painful for everyone involved.

  • SewingSiren

    The only thing I like is the hair.

  • Sarah

    God help the poor soul who plays THAT piano. *Shudder*

    • kimmeister

      He will need copious amounts of hand sanitizer.

  • Celticharpist

    “Ashish” is strangely reminiscent of “hashish.” Maybe that is what gave her the idea to smoke some before deciding what to wear.

    • Alicia

      I had to hold myself back from making the drug joke. Poor love.

    • wisenhar

      I actually misread the title as “Lindsay Lohan on Hashish”. That might help explain this outfit, though.

      • Boulderista

        I misread to it be “Lindsey Lohan in Amish … ” those two concepts in the same sentence about knocked me out of my chair. If ONLY Lindsey was Amish.

    • FrigidDiva

      That’s what I think every time I see it.

  • @Biting Panda

    Hooker, please.

    • Sarah

      Her love affair with strumpet hosiery is so bizarre.

      • KinoEye

        “Strumpet hosiery.” Love it.

        • Sarah

          I like me some, too, but it is like all the time with her. And she’s a fan of the black thigh-high, which just serves to give her short legs, whereas I think she thinks it’s sexy.

          • demidaemon

            You are probably correct. Unfortunately for everyone involved in putting these on and viewing them.

  • Jacqueline Wessel

    Giving Paul Shaffer a run for his money.

  • Counterpoint

    All I see is a 28 yo looking like 48 yo trying to pull tricks she learned as a 8 yo. That covers both styling and acting.

  • Danielle

    She’s almost unrecognizable.

  • littlevase

    Somewhere, Liza Minnelli is swooning.

  • Kayceed

    So I saw the thumbnail, got a glimpse of the hat, and immediately misread Lindsay Lohan in Amish. That would have made more sense than this.

    • KinoEye

      The Amish would be (rightly) horrified to be associated with this. Although, Amish life might just be the thing for Lindsay. She wouldn’t have to worry about dressing herself or putting on makeup anymore, she wouldn’t have access to drugs/alcohol, and no one would ever take pictures of her. Hmm. Not a bad idea, now that I’m thinking about it.

      • Kayceed

        Waitaminute! Isn’t there a reality show based on Amish life. Somebody call her agent on the double!!!

        • demidaemon

          There’s like eight gazillion. And they are pretty much universally horrible.

          • KinoEye

            Sadly, I watched one of them — Breaking Amish. It took me about two minutes to figure out that it was staged and fake on a whole other level for reality shows, which the internet confirmed for me. For instance: a pair of Amish people supposedly met for the first time when they left the community and started dating soon after. Turns out they’d been married and had a kid in real life. Kind of a shame, because I was actually curious about them and their lifestyle. The show teaches you precisely jack squat. Not that I was expecting to, y’know, learn anything from a show made by The Learning Channel. Not these days.

          • demidaemon

            The only one I’ve actually seen–and only because I could not find the remote to change the channel–was Amish Mafia. HORRIBLE. I can’t even put words into how fake it looked. It makes the Real Housewives series look like Emmy-winning television.

          • KinoEye

            Amish… Mafia. That seems like an oxymoron. What do they do?… Run a black market for raw milk and farm fresh eggs?

          • demidaemon

            Well, from the little I saw, they send people out to retrieve wayward children and some other stuff that doesn’t make sense, like drug trafficking? I really don’t know. It was really, really dumb and hard to follow. Not that i was trying, mind you, but still.

      • alyce1213

        Worked for Vanilla Ice.

  • Stella Zawistowski

    I’m getting Wynonna Judd out of this.

  • random_poster

    This is way over-styled. I don’t really care for the dress, but agree it would look 1000x better without everything else she has on. That hosiery is not a good look for her at all.

  • Imasewsure

    Gawd her makeup and that silly hat make her look like a aged but overly “refreshed” star in her 60’s…
    Plug in just about anyone who was famous in the 40’s and featured in an episode of the Love Boat or Fantasy Island in the 70’s or 80’s…. yikes!

  • Capt. Renault

    If she’d have taken a bit of treble, she could have looked really sharp, and not have fallen flat.

    • decormaven

      You played that bar so well.

    • AnotherG

      Alas, she too often succumbs to some bass instict.

  • Tracy_Flick

    Stay with me for a second. You know how sometimes in a marriage where one partner is an addict/alcoholic, and everything is turbulent? And then they sober up and you think everything is going to be on the upswing now. But then they get divorced anyway, because it turns out that when sober, the person is still kind of a jerk and now you can’t even blame the booze. That’s how I feel about Lindsay and fashion. I expected when she started pulling her shit together, she’d start dressing better. But it turns out, it wasn’t the drugs. She just has bad taste. Such a disappointment.

    • Sarah


    • decormaven

      Called it on the nose.

    • demidaemon

      Sadly correct. Usually those with taste deficiencies are either a) not in the limelight b) rich and smart enough to hire someone to make up for said deficiencies or c) ladies of the night. I believe, unfortunately, Lindsey is none of the above, unfortunately.

  • enchanted216

    If you didn’t tell me who that was, I would never have guessed. So sad :(

  • wisenhar

    “When I am an old woman I shall wear piano keys
    With a big hat that doesn’t go and doesn’t suit me.”

    • kimmeister

      Oh man, if it had been a red hat with a purple ribbon . . .

  • Rhonda Shore

    it’s so tragic. I remember when “Mean Girls” came out thinking that she had a Liz Taylor type of real beauty and look what she’s done to herself.

  • MzzPants

    Hey, she’s bathed, not orange, and got herself a Letterman gig. Let’s not ask too much of her.

    • Lori

      I give her full credit for bathing and not being orange, but beyond that all I really want from her is to go away and stay gone. We just don’t need to be looking at her train wreck any more.

  • Cheryl

    I don’t know what a Frozen Braid is, but I actually don’t mind this kind of messy braid. I would expect any hair product called Frozen, would actually make the braid, tidy and controlled not messy, but whatever. And I like that it’s red, not that hideous blonde she was sporting there for a while. Her skin looks the best it’s been in a long time, too. I’m studiously avoiding talking about the outfit….because for some reason I want to be be nice today.

    • IMNAngryLiberal

      Frozen braid like the braid on one of the princesses in the movie Frozen. Clearly you have no small children in your life. My 4-year old great-niece has explained the movie to me several times (some recitations taking longer than the running time of the actual movie).

      • Cheryl

        You are correct Sir! (read that in Johnny Carson’s sidekick’s voice). The only chilluns in my life are big lanky teenage boys that wouldn’t be caught dead in a Disney movie. Off to Google this Frozen thang.

        • majorbedhead

          Frozen is a lovely movie. I took my girls to see it and then watched it all by myself one night, I liked it so much. But that Let It Go song will get stuck in your head for DAYS.

          • random_poster

            DAYS that turn in to WEEKS…

          • marlie

            Possibly the first Disney song that I can’t stand. UGH.

          • random_poster

            I do like the song. I just don’t like it on perpetual repeat mode in my head, and that’s more about me than the song. (I feel there’s a joke here about not letting it go.)

          • Qitkat

            Is that the one Adele Dazeem sang at the Grammys? 😉 Not a fan either.

        • IMNAngryLiberal

          Go out to YouTube and search for kids singing “Let It Go”. They are hysterical. I especially like the one where the little girl is singing and acting along with the movie and she passionately FLINGS OFF her tiara along with Elsa. You will, as other posters have noted, then be humming the damned song for hours, days, and weeks, but it is a small price to pay.

          • Tapetum

            I have a soft spot for “Google Translate Sings”‘s version of “Let It Go” – most of their stuff is funny, but the Frozen songs are hilarious.

      • kimmeister

        I haven’t seen it and do not have children, but have definitely seen its pandemic-like reach. I was just at the grocery store the other day, and two kids were belting “Let It Go” at the top of their lungs. Then others started commenting on it with benevolent approval – I was afraid it was going to turn into a flash mob singalong!

  • alyce1213

    Train wreck. Make that Circus train wreck. Well, at least she’s not orange as far as I can tell.

  • Jessica Freeman

    I saw her posting these photos on Instagram last night and thought it looked pretty bad WITHOUT the coat. She has no clue how to style herself. I really love the dress, but burn the rest of the shittery.

  • tallgirl1204

    This is the opposite of the previous post. Ms. Diaz was completely under– no — NON-styled. Ms. Lohan has piled on so much that the extras hide the super-cute dress as well as the still-pretty woman underneath all of that… stuff. Keep the booties and lose all of the other extras, and this would be a cute look. And if the hat is hiding a need for the trip to the colorist, well, it’s hard for me to imagine that she didn’t know about this appearance until the last minute– if you want to make a comeback, you need to get your schedule organized. If that wasn’t the issue, this dress and occasion would have been the right moment for a simple braid (which might be what is hiding under there).

  • stubbornthoughts

    She looks like she’s wearing Liza Minnelli’s back up wardrobe and face to the Oscars. This is a horrible, horrible thing.

  • Linderella

    You know what’s even sadder than the clothes? The face. If you hadn’t told us who this was, I honestly would not have recognized her.

  • Kent Roby

    If you listen carefully, you can hear the piano playing “Claire de Loon”.

    • majorbedhead

      That made me snortlaugh.

  • Shawn EH

    Lost it. Just done. If this is her twenties, what the hell is awaiting in her fifties? She’s already at full-on Sally Kirkland.

  • Denise Rambo

    The coat would have even been OK with the dress and a pair of nice shoes but that floppy hat has GOT TO GO! In fact, ALL floppy hats have GOT TO GO! FOREVER!

  •!/Space_Kitty Space Kitty

    Well, we *are* talking about her, so I guess she’s got that going for her.

  • Uncle Spike

    “How does she manage to look both her own age and 30 years older than it at the same time?”

    It’s called drugs and alcohol. She’s been giving Demi Moore a run in the cougar department for years now. I’m even reading Elizabeth Taylor (and not necessarily the young one), which…well, she did portray Liz in that Lifetime movie.

    She’s sui generis. Bless her addlepated soul.

  • Fred Vaughn

    Baby Jane Realness!!

    • YousmelllikeAnnaWintour

      “I’ve written a letter to Daddy…”

  • Columbinia

    She’s got her clothes and the paparazzi cameras. That’s what’s left of her career. I swear, there have been times when I thought she got herself arrested or cited just so she could dress up and walk the gauntlet of cameras on her way into court. If she showed up for court and no press showed up, she just might stop getting in trouble.

    • alyce1213

      Or do something REALLY awful for attention.

  • Chase

    Linds, it’s time and past time to put on a bra.

    She’s a little young to already be into her Liza Minnelli phase, isn’t she?

  • marlie

    I hate to say it, but LiLo manages to make anything she wears look trashy. That’s absolutely a cute little dress, but the thing-highs and the sloppy-looking makeup (in addition to the hair, the coat, and the hat), shove this way over the line into Tackytown.

  • Luzia

    TLo really don’t like braids. why is that? is that personal taste or is it fashion sin?

    • marlie

      I don’t think they summarily hate braids, just the sloppy, sometimes uber-trendy ones that aren’t necessarily appropriate for the outfit or the setting. I don’t hate a braid either, as long as it’s deployed correctly.

    • Laylalola

      Probably personal. Though, they generally aren’t fond of tussled women’s hair (with a few exceptions) and that I sometimes think is fashion — we’re still in the keratin straight era for white women, i keep wanting natural to come back –fashion that has been around so long it’s hard to know when it merged into a strong personal taste.

  • ModernDowager

    My first thought with that dress was “Liza”

    • Eric Stott

      My first thought was “Edina Monsoon”

      • YousmelllikeAnnaWintour

        “It’s La Croix, sweetie.”

  • YousmelllikeAnnaWintour

    LET IT GO.

  • Ashleigh

    This makes me very sad, even tho I can’t stand her. It’s like she spends every dime she can on clothes to show up for this, recycling those damn thigh high things, borrowing shoes from someone, and manages to pull off a sorta-smile. It’s just sad.

  • Eric Stott

    She HAS looked a lot worse than this in recent years.

    • OffToSeeHim

      She’s worn a lot sluttier and a lot more awful stuff… but does she really look healthy? To me she looks spaced out again, and like she’s trying really hard to enjoy herself. I just want to find out where she lives and go put my arm around her. Although if she wouldn’t listen to Oprah, why the hell would she listen to me? But she just brings out all my motherly instincts – is there really no Mom-figure or best friend or ANYBODY that would be excited that she’s going on Letterman and giggle and try on clothes and say, “Oh God, we’re way past knee-highs!” and they both collapse on the bed laughing because she was never REALLY going to wear knee highs with those boots on Letterman? I’m rambling, but… she just breaks my heart.

  • KendraMR

    Her hair looks like one of those $2 synthetic ponytails at Sally Beauty Supply.

  • Wink

    Cosmetic surgery, puffy face, multiple career comebacks, and in a few years we will have forgotten that she once had talent. She’s well on her way to becoming Liza Minnelli. Get her into some vintage Halston. Pronto!

  • Jenna621

    I actually didn’t mind the look until I hit the shoes. Good grief.

    • Vtg Fashion Library

      Those shoes terrify me.

  • crash1212

    A bra. The look could’ve used a perfectly fitted bra as well.

  • onefifteen

    Honestly, I think it’s a fun look.

  • bitchybitchybitchy

    The dress is cute, and is enough without the wackadoo hat, but truthfully Lindsay looks relatively healthy here, so I’ll give her a pass.

  • MarissaLG

    Lindsay and I are the same age and I honestly don’t feel like it’s age appropriate. Maybe it’s cute for a 17 year old, but me and Linds are pushing 30 and those knee-highs just ain’t gonna cut it. She looks and acts like a fool.

  • Scott Cooper

    Sequins even Liza could loathe.

  • Tom Markiewicz

    Boys, that definitely is NOT a fedora…

  • B_C_J

    The stockings/knee highs together with the booties make this eccentric yet cute outfit move into the “what was she thinking” category.

  • CatherineRhodes

    Her face is turning into Michael Jackson.

  • antonialee

    Train wreck.

  • VCR1

    Sorry for the ignorant question, but wouldn’t Lindsay be a great opportunity for a stylist who is trying to get his or her business launched? I would guess that it would be a resume builder to style Lindsay and make her look amazing?

    • alliekat9090

      It would be a wonderful opportunity if it werent for the fact that she listens to no one who tries to help her or offer good advice. She has blown off her sober coach, her life coach, her managers & even Oprah. She certainly would never listen to anything a stylist suggested.

      • OffToSeeHim

        Right, and then every time she goes outside, your budding new business gets a “plug” as everybody says, “WHO’S her new stylist? They must be insane!” I wouldn’t hitch my brand-new wagon to that star. I see where you’re going with that, but it’s just such a huge risk.

  • Michael Martin

    This outfit screams, “Yeah, I’m totally not sober anymore.”

  • demidaemon

    Well, somebody let her out again. And she got into Grandma’s closet too. Time to send out the Fashion Police.

  • alliekat9090

    This whole thing really makes her look mentally ill. Seeing as we now know, thanks to Oprah, that her entire wardrobe lives balled up in in cardboard boxes stacked to the ceiling, it explains why everything she wears always looks so wrinkled and dirty. I can see her rummaging about pulling out random things and saying “oh this is cool, I forgot I had this. It has to be chic because it has a designer label!. I’ll just give it a quick shake and wear it all on Letterman”.

  • ThaliaMenninger

    Huh. Never saw Liza as a redhead before. Oh, wait…

  • cocohall

    I’m getting Lara Flynn Boyle from these pictures. Another attractive young woman who felt compelled to distort her face to the point that she is virtually unrecognizable. My guess is that part of the draw of having procedures (other than fixing perceived flaws) is that these starlets are fawned over by the medical staff/doctors AND there may be access to painkillers as well. And you can pretend you are “sober” as long as you have a prescription. Which also might go a long way to explaining how this look came together. Because if this isn’t DWI (Dressing While Intoxicated) what is?

    Lindsey is so frustrating in that she had so much talent when she was younger. But you only need to watch a few minutes of either of her parents many public mudslinging sessions to know that she was working against very long odds from the beginning. Unlike Amanda Bynes who seems to have parents who are trying to act in their child’s best interest, Lindsey has two self-absorbed egomaniacs competing for media attention.

  • nycfan

    Looks like she raided Liza Minelli’s closet and make-up.

  • LambeeBaby

    Styled as a Drunken Wiccan Art teacher