Let’s be honest: Lindsay Lohan is everybody’s favorite trainwreck. After first hitting the spotlight as the cute 11-year-old girl in The Parent Trap, Lindsay has had an up-and-down career characterized by a weird mix of good film roles, drug problems, and struggles with the law. Lindsay’s gotten her life back on track in the last few years, but if there’s one thing that she never quite managed to get straightened out, it’s her fashion sense. Lindsay likes to get experimental with her outfit choices, and while sometimes they work out, they usually… don’t (to put it nicely). Some of these outfits look like they belong to a homeless person who just staggered out of a garbage can. Others are colorful and artistic but a little bit, what on earth is that? And some are meant to be classy and tasteful but somehow manage to completely miss the mark and come across as unbelievably garish. Despite the crazy party-girl lifestyle, Lindsay’s still a pretty attractive chick—now, if only she would dress like it. Here’s to hoping that a new sober Lindsay gets her fashion decisions straightened out soon because I don’t know if the world can take too many more of these ridiculous outfits.
20 Trying Way Too Hard To Look Classy
This outfit is aiming at classy, but it comes out somewhere between garish and trying too hard. First, we’ve got the fur scarf around her neck. What would Cady Heron say to that? Fur might be lavish and expensive, but it’s also a terrible use of natural resources and most socially-conscious celebrities wouldn’t be caught dead in it. But Lindsay’s just hanging out, seemingly obliviously, at some gala. Under the scarf, she’s got a black tank top (fine), but then she seems to have some weird glittery see-through pants. They seem kinda cool at first glance, but then you realize it’s the kind of cool of a fifth grader who just learned how to use sparkles to make herself all glittery. They seem to be showing off way too much for the muted casual look she seems to be going for.
19 Looking Like She’s Wearing A Housecoat
Geez! What even is this? In this picture, Lindsay’s wearing a striped suit that seems to be molded after a bathrobe. There’s nothing flattering about this onesie at all, and Lindsay trying to make it look good by flouting it in public makes it look that much worse. Literally, anything would be better. First of all, the thing has about three different colors, and all of them are hideous. Then, there’s the way the lines run together to make the whole thing kind of dizzying to look at and then there’s the fact that the thing covers her whole body, so there’s no relief from the horrifying pattern. Seriously, I think I just had a bad acid trip just from looking at this pic. Hopefully, Lindsay looked at the paparazzi shots of this the next day and at least realized that she’d made a horrible mistake.
18 Wearing A Green Dress Cut Way Too Short
This is a shot of Lindsay repping a short-cut green dress at Gabrielle’s Gala in 2014 for cancer research. While Lindsay was widely praised for this outfit in the aftermath of the event, we can’t, for the life of us, see why. The green on the top of the dress stands out like overall straps holding the thing together, and having it cut so short at the bottom makes for a jarring effect. It’s like the dress just forgot to end. It’s a pretty revealing look, which will appeal to those who like the risqué look but just kind of makes the whole thing look weird. But even if the overdone dress didn’t work for everybody, at least the event was for a good cause, so that’s something.
17 Trying To Be A Tiger And Tinker Bell All In One
This is another shot of Lindsay trying way, way, way too hard to look classy and failing miserably. We’re not sure what this outfit is supposed to be, but whatever it is, it was a major factor towards her being named the Worst Dressed Star of 2012 in the Boston Globe. It looks like she tried to mix a tiger with a Tinker Bell with a terrible tan, with predictably atrocious results. There’s no unseeing this eyesore, but at least everything kind of matches, right? We’re hoping Lindsay doesn’t design her own clothing because at least then she can fire whoever outfitted her in this. But hey, between her Playboy shoot, embarrassing turn on SNL, and stalling movie career, 2012 was a rough year for Lindsay. Maybe looking good wasn’t her number one priority. (If you know what I mean.)
16 Looking Like She Forgot Something
Yikes! Here we have Lindsay wearing what appears to be no pants. We’re not sure if her baggy shirt is just covering up her underthings or if she really is bottomless, but either way, there’s nothing about this photo that’s flattering. It’s unkempt, weird, and a little confusing—sort of like Lindsay’s whole life. The fact that she’s wearing high heels and a rumpled top makes it look like she is at some classy event where she managed to get into enough wine (or something else) to leave without taking her pants with her. The weird thing is that she looks alert and focused in the photo. Is it really possible that this ridiculous getup is an intentional fashion choice? If so, we think that might be even worse. Put some pants on, Lindsay. Nobody needs to see that.
15 Looking Like A Thrift Shop Band Chick
In this photo, Lindsay looks nothing if not totally average. She’s rocking the ruby locks that got her famous in the first place, but with the shades, a washed-out t-shirt, and torn-up jean shorts, she looks like a teenage girl on her way to a concert. The tucked-in nature of the shirt isn’t flattering, but on the whole, the worst thing about this look is how totally like a nobody this makes her seem. We want to ask her when the last time she took a shower was. Does she think it’s still the 70’s? And what’s with her holding two phones to the same ear at the same time? It looks like Cady took trying to be the popular girl too far, and now she’s as worn out as that t-shirt.
14 Wearing A Nice Dress With A Slit Cut Way Too High
In stark contrast to the last pic, this is Lindsay erring too far in the other direction. She’s wearing a dress that would look super fancy, glamorous, and tasteful... except that the slit is about a foot too high. While for some celebs, showing off a little under a gala dress might be a fun little tease, with Lindsay’s history, everyone just looks at this and rolls their eyes. There’s nothing tasteful about wearing a full-length dress that doesn’t even cover up a tiny bit of leg. It just makes it look cheap and like she’s trying too hard. And if there’s one thing we’ve noticed with Lindsay, it’s that when she tries at all, she tries way too hard—there’s just no middle ground for this movie star. On the plus side, at least from the waist up, this is a good look.
13 Looking Like Someone Who Hangs Out At Burger King
Here we have Lindsay trying to bring the 90’s back, as she rocks a plaid button-up shirt and sips on a fountain soda. Between the black-and-white, the style, and the old-fashioned drink, this shot could be an outtake from the movie Singles, which is all about broke musicians in Seattle before grunge ever hit. This isn’t the worst offender on the list, but it does make Lindsay look more like a small-town rube than any type of celebrity. Maybe this is the look Lindsay would have gone for if she’d never found Hollywood—just hanging out at the Burger King with her lumberjack buddies, cracking jokes, and sipping on Coke ‘til midnight on a weeknight. Sounds like quite the life, right?
12 Wearing Too Many Colors
What the what? Here, Lindsay’s wearing some bright purple thing which appears to taper off into a ball of fire at the kneecaps. It’s an eye-catching look, but it’s also offensively bright and not something anyone should ever be caught wearing in public. In her defense, though, this is actually an outfit worn by her character, Lola, in the 2004 movie Confessions of a Teenage Drama Queen. Just think: this was Lindsay before all the drama, back when she was still wowing us with her cute looks and natural acting talent. And she still dressed terribly! It’s good to know that time and fame hasn’t changed Lindsay too much. Maybe she should go back and talk to the costume director from that film because it seems like she may have learned a little too much about style from that set.
11 Looking Like A Secret Agent With A Bad Tan
Now this, this is just awful. In this photo, Lindsay has managed to mix jet-black hair, dark glasses, and a dark shirt with a horrendous tan that just makes her look like a mangled Barbie doll. Her look here is low-rent Russian spy chick—someone who got the idea to imitate a sexy dark-haired Soviet spy skulking around in dark clothing but totally failed to execute. On the one hand, it’s not Lindsay’s fault that her orange tan clashes so horribly with the all-dark look. But then, on the other, isn’t it her fault? Shouldn’t she have been able to look in the mirror, recognize the tone of her skin, and say, “This is a terrible idea.” On the other hand, maybe if she’d avoided those tanning salons in the first place, she wouldn’t have this problem…
Sorry, Agent Lindsay.
10 Wearing A Pink Dress That’s Way Too Loud
Ugh. This is another shot of Lindsay trying way too hard to stand out in a classy setting and coming across as simply garish instead. This silk pink dress looks like something that was commissioned for royalty but then thrown in the trash because it was deemed too hideous. We’re not sure what Lindsay was really going for here. The floral prints completely fail to make the dress pop; instead, making it look like the dress that someone who didn’t know the bride wore to a wedding to try and make it look like she fits in with the bridesmaids. The worst thing about this dress is that it’s just trying so incredibly hard. If she’d just worn a t-shirt and jeans, it would have looked better only because it wouldn’t have been so painstakingly obvious that she was trying and failing at high-end fashion.
9 Trying To Look Like A Country Girl
Here we get Lindsay rocking a casual look as she prepares for a joyride on an ATV. She’s gone with her low-rent raggedy jean short look here, which wouldn’t be so bad except that she decided to rock enormous aviators that still try to say “movie star.” Overall, this look wouldn’t be so terrible for a typical back country girl just hanging out, but realistically, we know that Lindsay’s not really cut out for that kind of life. I mean, it’s cute that she wore the cut-off jeans to prepare for the off-road mud splatter, but was a collared white shirt really the right choice if she’s really planning on doing serious off-roading? Newsflash: dirt and white clothes don’t mix.
In general, this look tries to combine movie star Lindsay with country bumpkin Lindsay, and the results are mixed at best.
8 Trying To Revolutionize Plaid
Here Lindsay goes back to the plaid. But instead of a trucker shirt, she’s tried to make it fashionable by wearing it as a dress for a stylish photo. Unfortunately, the whole look kind of misses the mark. Really, who’s going to be wearing a plaid dress to prom? It just looks halfway between classy and cheap. It’s like the dress that your mom stitched for you when you couldn’t afford to shop at Walmart for a Halloween costume. Even worse, Lindsay’s wearing makeup in this shot which makes her face almost unrecognizable. Even if Lindsay is a plaid girl at heart–and it seems like maybe she is–this is not the way to go about it. Maybe she should go back to plaid shirts and jean shorts. It may not be the most fashionable, but at least it’s a recognizable look.
7 Looking Like A Piano
Oh, Lordy. Did we mention that Lindsay won an award for worst-dressed celebrity? There’s nothing classy about wearing a black dress intended to look like a piano. Like, what’s the point of that? Was there a huge demand for women wanting to look like pianos? There’s nothing remotely attractive about that. If that wasn’t bad enough, she’s covered it up in a white trench coat which doesn’t do anything at all to improve the situation. She’s also wearing awful makeup, and overall, this is a look that belongs in a school play–where the kid who doesn’t know how to act gets to play an inanimate object–and not out in public. Even worse, this outfit doesn’t seem to be a gimmick. It actually looks like she’s trying to dress classy here.
6 Wearing A Pink Baseball Cap
Why is she wearing that hat? It would be easy to say that there was nothing wrong with this outfit if Lindsay hadn’t, for some reason, decided to add a bright pink baseball cap. While we appreciate that wearing a pink cap is a subversive way to assert her femininity while co-opting a male status symbol (the tilted baseball cap), she didn’t seem to take into account that it clashes horribly with the rest of her outfit. It’s like she had a handler who outfitted her in a decent look, and then she walked out of the changing room, grabbed the ugliest hat off the rack that she could find, and added it on without consulting her stylist. It seems like Lindsay just knows exactly how to ruin every outfit anyone puts her in.
5 Looking Middle-Aged
This one isn’t horrible. It’s just not the most flattering. Here Lindsay’s wearing the kind of puffy skirt usually reserved for women who are struggling a little bit in the weight department and need a subtle way to cover it up. Lindsay’s a good-looking girl who shouldn’t need to hide the shape of her legs, but for some reason here, she’s decided to wear this bulbous skirt anyway. The look aims at something dignified, but between the pose, the makeup, and the skirt, she looks more like a 40-something mom going to church than a movie star showing off her stuff. We know Lindsay’s been through a lot in her 31 years, but I don’t think it’s quite time for her to embrace middle age yet.
4 Trying To Look Like The Pretty One
This is a shot of Lindsay hanging out on the set of Ugly Betty with the star of that show, America Ferrera. While true to the name of the show, Ferrera’s hideous costume grabs the eye in this photo, and Lindsay’s not doing much better. She’s got her typical “trying too hard to look good” thing going on, with a striped top and glitzy jewelry that’s probably supposed make her look like the successful good-looking one next to Betty. But she can’t quite pull the look off because who are we kidding? It’s still Lindsay Lohan, the worst-dressed actress in Hollywood. Shortly after this photo was taken, Lohan was apparently kicked off the show for creating drama and not getting along with her co-stars. Sounds like the Lindsay we know and love!
3 Looking Confused About What Country To Represent
Here we get Lindsay dressed in all kinds of what the heck is that? We start with the Russia cap. It seems a bit weird for an American actress to represent Russia in the first place, especially with everything that’s going on in the USA these days, but if she wants to, I guess that’s her choice. Then we get to a sweater which has all sorts of writing all over it representing Paris. It’s hideous, but that’s not really the point. She’s already representing two different countries, and we’re only halfway through the outfit. Under the sweater, she’s got something completely different sticking out like a kid who forgot to tuck in her t-shirt. The whole look is uncoordinated and clashing and really constitutes a true fashion crime.
2 Looking Like All Of The Animals
Here we get a shot of Lindsay rocking a whole lot of fur and leather. Setting aside for the moment that it looks horrible, this getup is also incredibly thoughtless. How many animals died for this photo? And the getup itself doesn’t seem to do Lindsay any favor. She seems to have decided to go all-in on the animal theme with spotted high heels but throwing it all together. It just looks gross. For some reason, she’s combined thick fur on top with bare legs on the bottom, which just doesn’t make any sense logically—if it’s cold enough to wear the fur, then why doesn’t she need any pants? Combine it all with an unappealing tan, and this is yet another look where Lindsay’s trying way too hard to flash some fashion sense and failing miserably.
1 Looking Like The Cowardly Lion
Here we get a shot snapped by the paparazzi of Lindsay going out for dinner for her grandmother’s 94th birthday. While we appreciate that even after all she’s been through, Lindsay keeps her family close to her heart, but what on earth is she wearing in this photo? It seems to be a kind of collared fur coat type of thing that covers her up completely and makes her look like a stunt double for the Cowardly Lion in the Wizard of Oz. You’d think that dinner with the fam would have been a great time for Lindsay to dial it down and not make everything about her horrible fashion sensibility, but apparently, Lindsay didn’t get the memo. As usual, she’s trying way too hard to look like...something. Maybe next year, for Grammy’s birthday, Lindsay can just wear a casual dress and a decent jacket like a normal person.