Katie Holmes has been in the spotlight for two decades now. She first became famous in 1998 when she landed the role of Josephine ‘’Joey’’ Potter on The WB (now The CW) teen drama Dawson’s Creek. She then successfully transitioned to the big screen with the movies such as Disturbing Behavior and The Ice Storm while still shooting Dawson’s Creek. After Dawson’s Creek finished in 2003, Katie was able to focus even more on movies, starring in Christopher Nolan’s Batman Begins in 2005 as Bruce Wayne’s childhood friend and sweetheart Rachel Dawes.

From 2005 onwards she became a tabloid staple thanks to her relationship with actor Tom Cruise. They were considered a super-couple, being given the nickname ‘’TomKat’’. They caused a lot of media attention which was often controversial, especially due to their heavy involvement with Scientology. Katie gave birth to their daughter Suri, and the couple got married in 2006. Katie filed for divorce in 2012, breaking away from Scientology and gaining full custody of Suri.

While Katie has regularly been included on ‘’Most Beautiful’’ lists, she never makes the ‘’Best Dressed’’ lists, and anyone who has seen her outfits knows why! If you’re unaware of her weird dress sense, stay tuned to see some of Katie’s weirdest outfits.

Could This Outfit BE Any Worse?

Oh dear. Where to begin? This is one of those outfits where every item would be terrible enough on its own, but then they all get thrown together and the results leave everyone else with second-hand embarrassment. The mustard yellow shirt is not the best shade (despite Katie usually pulling off yellow quite well), its neckline is weird, the sleeves are horrible, and let’s not even get started on the weird designs on it! The overalls are truly quite wacky, with the super-deep neckline and the weirdly-cropped trouser legs. The shirt and overalls are terrible both apart and together, but those ugly grey sandals really are the cherry on top! The bag and sunglasses are actually quite cute, but there’s no saving this mismatched and bizarre outfit! However, Suri’s polka dot dress is adorable!

Weirdest Pants Ever

Katie Holmes has always been a fan of scarves, and in March 2009, her scarf of the month seemed to have been this blue tartan one, which kind of looks as if it was made out of someone’s old tablecloth. Although the scarf is a bit on the weird side, with the right outfit, it could actually work, especially with Katie’s dark hair. In this case, however, the rest of the outfit is just terrible! The shirt is fine and it matches the scarf, but what is going on with those pants? How could you even describe them to someone else? Are they cropped tracksuit bottoms? Do those even exist? They’d be bad enough on their own, but Katie decided to pair them with footless tights and black pumps! That is just unforgivable!

Jumpsuit That Is Not Exactly Flattering

Yikes, what is going on here? Katie decided to wear this outfit to the after party of the official opening night of her Broadway debut in the revival of Arthur Miller’s 1947 play All My Sons. Although her performance was well-received, this outfit sure isn’t! The black lace top clashes horribly with the cream white suit, which isn’t really that nice to begin with – it’s not the ideal white suit for Katie, and the billowy pants are just plain awful. The gold necklace is really quite tacky and makes an already bad outfit look even worse. The sandals are fine because they are a classic and versatile style, but they just look funny beside these Aladdin-esque trouser legs! Katie, if you don’t have a stylist – hire one, and if you’ve already got one – fire them!

Big Bird, Is That You?

This was Katie’s outfit for the 2014 Met Gala. Sure, Met Gala outfits are known to be extravagant and not something that you would wear to any other formal event, but there is a fine line between gorgeous extravagance and a terrible outfit choice, and Katie is so far past that line that she can’t even see the line anymore! Huffington Post even declared her to be the worst-dressed person of the night, and they certainly didn’t make the wrong choice! This off-the-shoulder gown looks as if it was inspired by Gone With the Wind, but with the crinkly satin skirt, horrible shade of yellow, and red beading which resembles a blood stain, Katie’s not so much like Scarlett O’Hara as she is like Big Bird who just got stabbed! The messy hairstyle certainly doesn’t help!

Grandma Holmes' Cardigan?

Katie has always been a fan of cardigans, but there is a difference between a cute cardigan from H&M and a cardigan that your grandma wears! This actually could have been a really cute outfit – the white blouse is a simple and classic style, it goes well with the suit trousers, which suit Katie very much, and the ankle boots also work well. But that cardigan is so bad that it ruins everything! Katie was only 33 when she wore this cardigan, but she might as well have been 83! It also really clashes with the red and black bag and what appears to be Suri’s pink scrunchie around her wrist. Mind you, she’d just split up with Tom Cruise, the poor woman was probably still traumatized from 6 years of Scientology!

Dad's Cardigan Over Cocktail Dress

Sure, Katie has mentioned multiple times that she sometimes prefers buying clothes in the men’s department. However, there’s a difference between throwing your boyfriend’s hoodie on over your jeans and T-shirt when you’re a bit chilly and grabbing a big chunky cardigan usually worn by old dudes and wearing it over your dress! This grandad-style cardigan isn’t worn even by the most dedicated hipsters out there. Somehow Katie thought it would be a good idea to throw it over a red satin dress, which wasn’t all that cute of a dress to begin with – it is badly creased and the asymmetrical hemline isn’t as fashionable as it is just plain weird. Then you have the brown hat and shoes that don’t match anything. All in all, this is a truly mismatched outfit.

When Fitness Is At 8 But The Party Starts At 9

Someone could say that Katie Holmes has possibly the worst street style ever, and this photo proves that that wouldn’t be too bold of a claim. The red cheetah-print leggings are definitely an acquired taste, but they might work with the right outfit and in the right place, for example, with some plain sneakers at a rave. But wearing leggings with heels has got to be one of the biggest no-go style codes! You can mix casual and classy, but not like this! The heels themselves are actually really pretty and suit Katie’s frame, but the gold parts look tacky beside those leggings. The denim shirt is also fine, but it just doesn’t go with the leggings and the heels. The silver backpack with red stars just makes the already-bad outfit even worse!

I Woke Up Like This?!

This outfit is what happens when you take the phrase ‘’I woke up like this’’ too literally. Casual outfits are great, especially when you’re just running errands, but this is a bit on the messy and slobby side. What’s hilarious is that this outfit is actually worth more than other people’s entire wardrobe! The tracksuit bottoms are designer (and also from the men’s department!), the espadrilles are from Chanel, and the handbag is Celine and retails at around $2500! Sure, Katie’s rich, but it’s silly spending so much money on leisure wear, especially when the sweatpants are so big that you have to roll them over on the waistline to keep them up! Also, when wearing a purple sports bra, it’s a good idea to wear a darker T-shirt over it instead of a sheer white one!

Stirrup Leggings

Ah, the ‘80s. So many weird and wonderful fashion items came from that period. Some of them have been welcomed back with open arms, probably because everyone was secretly waiting for them to be fashionable again, whereas some should just be left in the ‘80s as they were ugly even then. Stirrup leggings are firmly in the second category. They’re uncomfortable, impractical, and they just look tacky. Katie attempted to revive them in 2008, but thankfully, it didn’t take on and become a trend. Well, they maybe would’ve made a comeback if they’d been worn as part of an awesome outfit, but awesome this was not! Sure, shorts and tights are a popular combination, but it works better with hot pants and thinner tights – these shorts just don’t go with the leggings, and the heels don’t go with either of them.

Flower Power?!

Floral jumpsuits can be really beautiful and fashionable, especially when paired with great accessories, but this jumpsuit is neither beautiful nor is it paired with great accessories. The actual floral pattern of the jumpsuit is more reminiscent of someone’s curtains, and the neckline is just too much with that busy pattern. The color of the cardigan clashes horribly with the jumpsuit, and it is also a style of cardigan that is more often worn by old men! The brown peep-toe boots aren’t all that nice to begin with, so naturally, they also clash with the jumpsuit, and the belt is unnecessary because it – you guessed it – clashes with the jumpsuit! Basically, everything clashes and will clash with this jumpsuit because it is horrible and should be burned. Suri’s adorable outfit would’ve been a much better choice for Katie!

When Stripes Go Wrong

Black and white stripes usually go really well with red accessories, for example, a cute black and white top paired with black skinny trousers and red heels. This outfit makes a theoretically good pairing but turns it into something awful. Katie’s wearing a shapeless black and white top (or is it a tunic?), which does her no favors, and has paired it with black dress shorts, black footless tights, and red pumps. The dress shorts are cute, and the pumps would probably work with another outfit (for example, a flowing dress), but it’s just all so mismatched. Footless tights were probably one of the worst trends of the ‘00s, much like the stirrup leggings of the ‘80s, and they certainly weren’t meant to be worn with dress shorts, and dress shorts weren’t meant to be worn with ballet pumps!

Tablecloth Blouse

Okay, sure, checked blouses are one of the cutest items of clothing around and they go really well with jeans. The thing is, the checked pattern needs to look nice, the jeans are also supposed to be nice, the outfit should be accessorized with the right things, and you should make sure not to accidentally flash your bra! Whoops! In this case, the pattern of Katie’s shirt looks more like the pattern of a tablecloth from a pizzeria in New York. Well, Katie spends most of her time in New York, so maybe she was inspired by those tablecloths? Also, it would have been a good idea to have checked if any of her buttons was unbuttoned. The jeans and wedges are separately okay, but this is a mismatched outfit.

Yellow Peril

To be honest, this is actually a really, really cute yellow dress, and Katie looks gorgeous in the right shade of yellow, especially in a dress that shows off her long legs. So why has this made the list of her weirdest outfits? Well, a dress needs to be styled properly, and Katie has failed miserably at that! That denim jacket just doesn’t go with the dress, and those ankle boots were a downright terrible choice! And that is how you completely ruin a perfectly cute dress. Instead of a cute summery outfit, Katie’s ended up looking like she’s cosplaying a Minion! And all because she doesn’t know how to match clothing! A few wrong choices have given her yet another mismatched outfit. Mismatched outfits seem to be a staple of Ms. Holmes’ wardrobe, don’t you think?

Can She Even Breathe In That?

Okay, this outfit is for her role in the 2016 movie All We Had (which was also directed by her, go Katie!), but it’s so bad that it had to be included! Poor Katie, not even her characters know how to dress! Denim dresses can be really gorgeous, but the first rule is to wear something in your size, and this rule has been broken so badly that it looks as if Katie has squeezed herself into a dress meant for a petite teen! While Katie’s a slim woman, she’s also very tall, so mini-dresses will be extra short on her if she’s not careful, and this one is not only too short, but it’s also too tight. In fact, is it even possible for her to breathe while wearing it? It’s definitely never easy being an actress!

Denim Failure

Katie has always made some interesting choices when it comes to denim, but the reason why she’s not an edgy fashionista is because she pairs them with some seriously questionable items of clothing. The boot-cut jeans aren’t for everyone, especially because they’re a bit on the long side, but pairing them with plain footwear was a decent choice. The top half of the outfit, however, is a completely different story. That white jacket, blazer, cardigan, whatever it is, is a crime against fashion! It looks as if someone was inspired by Jackie O but then designed it while tripping on acid or something! The brownish top also needs to go. Oh Katie, why are you like this? You really need to hire a good stylist!