Celebrity style is endlessly fascinating. When you want to look chic and casual, you might throw on a t-shirt and a pair of ripped jeans, and sure, you look pretty cute. But when you see your favorite celeb wearing the same outfit, they honestly look like the most fashionable person ever. You don't know how they do it. Well, okay, you kind of do: they have more money and resources and access to designer clothing than you do. Sigh.
There are some stars who honestly have a super strange sense of style. You look at photos of them on the red carpet or just running errands and you think, "What the heck were they thinking?" It just doesn't make sense that someone could pull together an outfit like that, but yet someone did. There are other stars who can totally rock any type of look, no matter how weird or unique. Those are the stars that you basically bow down to because, hey, that's some serious talent right there.
Whether they're grabbing a coffee, have just worked out, or are headed to an event as fancy and elegant as they are, celebrities have their own way of dressing that can be thrilling or confusing AF. Check out our list of 10 celebs who pulled off the weirdest looks... and 10 who didn't end up looking quite as chic!
20 Pulling It Off: Kim Kardashian
You probably wouldn't expect to see Kim Kardashian rocking both baggy high-waisted pale blue sweatpants and sneakers, but... here she is. And she really is rocking them. Because even if this is a bit of a strange outfit, she looks pretty good. With her gorgeous long hair, she truly makes this look work.
This just proves what you knew was true all along: Kim Kardashian is truly The Queen Of Fashion and looks good no matter what. Like really no matter what. She can pull on these pants and shoes and add a massive shiny black coat that says "LOST" and still manage to look as sophisticated and elegant as if she was wearing a super fancy dress. You get it: Kim's the chicest around and you totally bow down.
19 Should Just Stay Home: Mary-Kate Olsen
This photo is from a few years ago when Mary-Kate and Ashley Olsen were known for their boho chic looks. The thing about those outfits is that sometimes they made them look like they were swimming in their clothes. They're both pretty tiny and outfits like this one are just too overpowering.
Mary-Kate's baggy jeans with a massive hole in the knees, long sweater, hippie-inspired white dress, and massive scarf just don't look that great together. You know that the Olsen twins are super fashionable and of course, they've got their amazing fashion lines these days, but this is just one outfit that is a bit too baggy for your taste. One baggy element is usually enough for an outfit but it's just way too much when everything that someone is wearing is so baggy.
18 Pulling It Off: Gigi Hadid
Gigi Hadid is known for being really stylish. She always looks like the very picture of fashion perfection, whether she's wearing a crop top and leggings because she's just worked out or she's wearing a comfy sweatshirt and jeans. This outfit is a bit more confusing and, let's face it, it's kind of weird. And yet she pulls it off with style and grace.
You might not think that a super baggy sweatshirt with a rose on it would work with the baggiest light pink pants around, let alone matching pink sneakers, but it does work. This is totally one of those weird outfits that you see on a celebrity and can't believe that they can make it look awesome, but they do since they're just such a star. Gigi always has a ton of star power and this is one of those times. You might not wear this, but you can admit that she looks great.
17 Should Just Stay Home: Miley Cyrus
Miley Cyrus is another celebrity who is known for wearing things that don't really make much sense together. This is definitely an example of that, but of course, she doesn't care what anyone thinks about what she's wearing. You definitely love and respect that about her, even if you don't always like her outfit choices.
Let's talk about those pants for a second. They might be okay if she had kept the rest of her outfit simple, but her baggy t-shirt and leather jacket and the scarf tied around her neck don't really do the pants any favors. They just have such a strange, confusing pattern on them. You're definitely not against patterns and even patterned pants can be cute sometimes but these just aren't that pretty. Miley's scarf and heart sunglasses just don't work with everything else. This isn't one of her best looks.
16 Pulling It Off: Selena Gomez
Selena's rocking some serious holes in those jean overalls. It would be weird enough to wear full-body overalls, let's be real here since it's not the 90's anymore and chances are, you only wore those when you were a little kid. That was totally the trend at the time and you felt like the most fashionable person around. Maybe you even wore colored overalls. Now that was something.
Selena looks so pretty, though, even though her overalls are super torn and honestly look like she took a pair of scissors to them. Even though it's a bit strange that her overalls are open and revealing her white cropped t-shirt, that looks pretty cool, too. Okay, it looks extremely cool. She just looks awesome in general.
15 Should Just Stay Home: Ashley Olsen
This is just a really confusing outfit since that sweater is just way too big. It would be way too big for anyone, really, so you don't think that this would look that great on anyone.
It's also a confusing style since one side is a plain beige (but kind of a greenish beige which isn't the prettiest color out there) and the other side is grey and black striped with a huge green patch on the bottom. Um, what is happening here?! You just don't get it. The fact that Ashley Olsen has paired this with a leather jacket and black boots is even more confusing, but it's just a confusing outfit in general so, really, you're not going to get any kind of clarity on this.
14 Pulling It Off: Kendall Jenner
Would you wear a red and white striped suit, with a jacket and pants? And would you pair that suit with white shoes? No. You probably wouldn't. Because that doesn't sound even remotely chic or cool or pretty. It doesn't sound like something that one of the most fashionable young models around would wear, not to mention a member of the Kardashian-Jenner family.
Well, here's a photo of Kendall Jenner wearing a suit that's red and white striped, and she looks really beautiful. She's definitely someone who can pull off a look like this and you have to admit that it's one of the coolest things that you've ever seen her wear. Weird? Sure. Gorgeous? Yes, absolutely. She even manages to make a fanny pack kind of situation look really awesome.
13 Should Just Stay Home: Kristen Stewart
Kristen Stewart doesn't look like herself here, so if we didn't tell you it was her, you might not recognize her at all.
Her plaid pants aren't the worst things ever, but with this plain white t-shirt and suspenders and her very messy hair that looks kind of unwashed, they don't look as chic as they could. Sure, you get that Kristen is one of the coolest actresses and that she doesn't care what people think or say about her. She's not a star who cares about being famous and she just wants to focus on her acting, which you totally get and you definitely think that she's got tons of talent. This just isn't her best outfit ever. It's honestly just not super flattering.
12 Pulling It Off: Hailey Baldwin
Hailey Baldwin's wearing both blue and turquoise in this photo, and you might never think that those colors would look good together. After all, those are hard shades to pull off even on their own, orange in particular. The outfit that she's wearing -- a massive blue coat with yellow patches, a huge orange turtleneck, orange pants, and blue shoes -- is even harder to pull off.
And yet she looks incredibly chic. She looks exactly like the cool young model that she is. You might never have picked something like this out and you still might never want to wear something like this, but Hailey looks amazing. She really looks wise beyond her years and like she really has her own unique and fabulous sense of style.
11 Should Just Stay Home: Jessica Simpson
There's a lot going on here and it's all pretty confusing. Those pants would honestly be weird enough because it's hard to believe that they really look like that. At first glance, it kind of looks like she's wearing a skirt, but nope, she's totally wearing pants. They're that huge and there is that much fabric.
How did she walk around without tripping?! That's the first question that you have and you're probably not alone there. That seems like a pretty logical thing to ask. The second question that you have is why she chose to pair those pants with that jacket. Because the jacket is fur and multi-colored and just really confusing and loud and too wild. It's just all too much. Phew. You need to take a deep breath now.
10 Pulling It Off: Katy Perry
It's a bit strange to see Katy Perry in such a girly AF outfit, isn't it? You're used to seeing her with colored hair for one thing, so the fact that her hair is brown and pulled back in a plain low bun is shocking enough.
She kind of looks like a teenager exploring her punk rock side in this patterned dress and cardigan and combat boots... and she looks like the coolest person ever. It all really works. You might not have thought that this outfit would look so good but Katy honestly looks really beautiful and fashionable. It just goes to show that everyone has their own way of putting clothes together and that originality is the best and most fun part of fashion.
9 Should Just Stay Home: Bella Thorne
Bella Thorne is known for wearing really, really confusing outfits. Like the kind of outfits that make you say "WTF?" because you can't imagine that someone would ever put those items of clothing together. This is one of those outfits, and it's hard to say that you like it... because you really think that it's weird. It's up there with her most confusing outfits.
Any element would be bad enough, from the clunky white boots that say "Fragile" on them to the red fishnets to the bra top to the huge white sporty jacket. Add her bright pink hair and huge white sunglasses and way too many accessories and the whole thing just kind of gives you a headache. This is a fashion don't if there ever was one... Sorry, Bella.
8 Pulling It Off: Kylie Jenner
Kylie Jenner is known for looking stylish at all times. Like literally at all times. She can make a plain t-shirt or baggy sweatshirt look like a ballgown. It's just one of her many talents and skills.
This is one of those times. Kylie looks incredible in this long red t-shirt and tall black boots. You would never, ever think that someone could leave their house in a long t-shirt and boots and call it an outfit. This looks like something that you would try to wear as a teenager and your mom would yell at you for an hour about how you could never go outside looking like that. But, hey, Kylie makes it work and even her bright blue hair looks really cool. You're a big fan of the whole thing, even if it's a bit of a weirder outfit than what you typically see the star wearing.
7 Should Just Stay Home: Anne Hathaway
Anne Hathaway usually looks as chic as her short hair, but these pants are way too baggy to be cute and that's just not something that you would ever want to see anyone wearing.
Sure, the angle of this photo isn't the best and makes her pants look even wider, but still. You're still not into these pants. Maybe, just maybe, they would look okay with a plain white or black sweater or something, but you definitely don't think that they look that good with this red t-shirt. The pants are just really distracting you. They just really seem like a strange outfit choice. Couldn't she have worn leggings or jeans or something else? Why these pants? Maybe they're having a moment with celebrities or something but you're just not sure that they work.
6 Pulling It Off: Kendall Jenner
Suspenders are kind of a weird thing to wear. You never see anyone wearing them, do you? No, you definitely don't. Were they ever a thing?! Maybe guys would wear them on 90's sitcoms. That's really the only time that you can remember seeing them.
You definitely wouldn't expect to see Kendall Jenner wearing suspenders. This outfit is a surprise because she looks so good in something that you wouldn't think would work. It not only works but she looks like an incredibly fashionable person. Her beige turtleneck sweater, white skirt with massive slits on the side, suspenders, and white sneakers look great together. You might have no clue how this looks so good. Maybe it's just the fact that Kendall is wearing them and she makes everything look amazing.
5 Should Just Stay Home: Britney Spears
Sure, Britney Spears has a totally amazing figure and all those hours of dancing and performing pay off for sure, along with the hours that she puts in to train and work out. You love her and have always loved her super fun pop music. You just don't really love this outfit.
From the pink Ugg boots to the jean shorts to the super cropped top (which is more of a crop top than you might have even thought existed), well, it's just too much. The jean shorts would be totally cute and fine with another top, and the top might even be okay if she was wearing jeans. There's just something about the combination of this top with these shorts that isn't the best. Sorry, Brit. Your music still rocks.
4 Pulling It Off: Elle Fanning
Yes, Elle Fanning is wearing pajamas. Yes, she's wearing pajamas and walking around. Yes, she's famous and went outside in her PJ's even though people could definitely see her.
Did she care? No. And she shouldn't care because she looks so cool. She looks like she's wearing the most beautiful designer outfit ever. Maybe it's the big smile on her face or how comfy she looks, but you have to admit that this look is really working for her. You're probably not ever going to want to walk around in your pajamas, but this has probably changed your perspective on what fashion really is. As long as someone looks confident in what they're wearing, they really can look good in almost anything. It's pretty cool when you think about it. Plus she's wearing sunglasses on top of her head, so you know that she looks awesome.
3 Should Just Stay Home: Khloe Kardashian
Khloe Kardashian always looks absolutely amazing but this headband is really distracting. Like really distracting. It's the kind of thing that you would expect to see on someone going to the gym... or going to an 80's costume party. It's just too old-fashioned for the rest of the outfit and pulls your attention away from the other elements of the outfit.
Okay, so her massive fur coat is pretty distracting, too. This would have been the coolest and prettiest outfit ever, if she wore a simple blazer or something over these skinny jeans and this top, and if she ditched the headband for a sleek ponytail or something. Khloe just doesn't look like herself since you never see her wearing something like this. The best style decision that someone can make is to truly look like themselves, right?!
2 Pulling It Off: Katie Holmes
Katie Holmes is wearing a lot of strange things that somehow and magically go together in this picture. She's got a jean jacket, bright red sporty pants with a white and black stripe on one side and a black leopard-ish pattern on the other side, and black high heels. Oh, and a white backpack with red stars. You can't forget about that backpack. It's pretty cute and definitely something that you would buy and use all the time.
Honestly, it's hard to admit that this all works, but she looks pretty adorable. Sure, if she was wearing the jean jacket and backpack with a plain pair of black leggings, this might look a bit better, but that's okay. This is a quirky outfit and it's creative and you like it. Go, Katie!
1 Should Just Stay Home: Kourtney Kardashian
Kourtney Kardashian obviously looks super stylish all the time, but this huge dress and these strappy sandals are just a bit much together. They might look okay if she paired them with something else, but together? It's a bit overwhelming.
The thing with this dress is it's just a bit too wide and a bit too frilly. If it was a bit less frilly, it could be really cute. It's those two layers of fabric, right? The dress is also too sheer when you really look at it. It just doesn't look like the kind of thing that you normally see Kourtney wearing, so even though you love her and think that she looks great all the time, you probably don't think that this is her best look.