Britney Spears' 18 Worst Red Carpet Looks That Make Us Think She Dressed In The Dark

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The Princess of Pop has sported many iconic and amazing looks over the years, but not all of them have hit the mark (in fact, quite a few of them have been downright awful). There’s no doubt that Britney Spears is one of music industry’s most stylish and beautiful women on the planet. But over the years, Brit has treated us to some shockingly bad outfits on the red carpet. Well, she’s only human after all.

Even with gorgeous good looks and an entourage of stylists with you every step of the way, looking glamorous on the red carpet is never a guarantee (and these pics prove that in spades). Anyone remember the time when it looked as if a Denim store had thrown up all over Britney or when she went through the horrendous early noughties phase of wearing dresses over jeans? Ugh. We love you, Brit, but honestly, who told you this looked good?

Whether you’re too young to remember Brit rocking these horrible looks or have simply blocked them from your memory, we’ve taken it upon ourselves to remind you of the fashion atrocities committed by Ms. Spears throughout her career. When it comes to crimes against fashion, Brit did it again... and again... and again.

When Dresses Over Jeans Was So On Fleek

A lot of female stars of the late 90’s and noughties sported this weird look on the red carpet, but no look was more memorable than when Britney did it. The prize for “who wore it worst” definitely goes to Spears for this one. Perhaps it’s the overuse of baby pink or the matching boots. Or simply because it’s one of the most hideous outfits we’ve possibly ever seen.

The only way we can try and understand the whole ‘dresses over jeans’ trend (how on earth was this ever a trend?) is if we imagine that some people have a hard time deciding what they’re going to wear for an event and so they end up wearing both of their choices instead. Except, instead of getting the best of both worlds, you get this—a ‘marshmallow threw up on you’ look. Neat.

Dominatrix Britney

Anyone remember the time when Britney dressed like a stripper like it was no big deal? We do, unfortunately—it’s kind of hard to forget this image, isn’t it? Brit looks as if we’ve wandered mistakenly into a seedy pool hall full of Bikers and we’ve just insulted their leader. It’s hard to compute how she didn’t rethink this ‘look’ before heading out for the night. Even for the bizarre fashion decade that was the noughties, this was pretty atrocious.

Arm-length fishnet gloves? Check. S&M-inspired leather vest top and cap? Check. This was at the 2002 MTV awards, a whole year before Brit’s infamous lesbian kiss with Madonna at the 2003 awards. Looks like she was warming up for the shock factor with this odd biker chick look that was definitely more scary than sexy.

Denim. Denim, Everywhere

Oh. My. Gosh. If this doesn’t sum up the 2000’s (the other decade that fashion forgot), I don’t know what does. This is probably the most iconic Britney red carpet blunder of all time—the era when wearing denim on top of denim seemed to be somehow acceptable. Britney and her then-boyfriend Justin Timberlake treated us all to this fashion disaster at the 2001 American Music Awards, and we’ll never be able to block it out. Not now, not ever.

It’s one thing to pair two bits of denim together (I was guilty of wearing a denim jacket over jeans once or twice in my teens), but to have your partner come with you as your denim doppelgänger? Just no! It’s nauseating enough when couples or twins look alike, but no one would ever take it to this level. Truly horrifying.

Not Such An Innocent Girl

This red carpet snap was taken just hours before Brit temporarily shook the world with her X-rated stage antics while performing with Madonna and Christina Aguilera at the 2003 MTV Video Music Awards. By wearing a fairly innocent, cutesy white dress, it’s almost like she’s foreshadowing the complete opposite—the end of pure, girly Britney as we know it.

Although, on closer inspection, her outfit isn’t all that innocent. For one thing, her dress is so short and lacey that it may as well pass for a lingerie item. Also, the pearls and frilly detail kind of looks like she’s come as a naughty bride for Halloween (and the less said about the white PVC stripper boots, the better). Brit clearly wanted to stir things up that night (and boy did she!).

The ‘Shipwrecked’ Look

Yes, Brit, your abs are totally flawless here, but don’t you think you could have shown them off in a better way than wearing this? Britney’s trying (and failing) hard to convince us why well-stitched, complete garments are so last century! Her jumper doesn’t look intentionally cropped as much as having snagged a thread when she left the house and carried on unraveling until she got there.

I guess we have no room to talk about ripped and wrecked fashion in 2018 with cold-knee jeans and whatnot, but we’re generally a little more self-conscious about our tummies than our kneecaps. And besides, even with an amazingly-toned stomach like Britney has, this is not a good look. Whoever called this fashionable needs to reassess their lives just a teeny-tiny bit.

When Cargo Pants Ruled The World

If you never owned a pair or two of baggy cargo pants growing up in the late 90’s and early noughties, congratulations, you’re a very wise and sophisticated person. The rest of us, on the other hand, fell into the trap of thinking that these actually looked flattering, and it seems like the curse even took hold of our pop princess at one point too.

While receiving her star on the Hollywood Walk of Fame in 2003, Brit decided to celebrate the proud occasion by wearing an outfit that looks as if she robbed the contents of a ‘lost and found’ bin. Forget the fact her fluffy coat looks as if she’s skinned Lots O Huggin’ bear from Toy Story 3—the baggy, zip-covered, multi-pocketed cargo pants are definitely the cringiest part, as it reminds us of a time where some of us clearly didn’t own a mirror.

Morbid In Black

If it weren’t for the text advertising Glamour magazine in the background or the huge smile on Britney’s face, you could end up thinking that Brit was snapped on her way to a funeral in this photo. The all-black theme Brit has gone for here (not to mention the black fascinator hat) seems weirdly morbid-looking for a red carpet event. Maybe she was observing a respectful minute’s silence for the death of fashion?

Seriously though, if you were invited to Glamour’s ‘Woman of the Year’ awards and a star-studded after-party, is this the kind of get up you’d want to be seen in? Who knows how Britney’s mind really works when it comes to red carpet fashion, though? We love you, Brit, but you’re crazy to have left the house like this.

The Pink And Orange Maxi Dress

For those of you who have ever seen the third Austin Powers movie, Goldmember, this dress looks a lot like it’s ripped straight out of one of Austin’s 70’s-inspired wardrobes. Yuck. Britney has a figure to die for and was only 19 at the time this was taken—you’d think she could do no wrong when it comes to wardrobe choices. Sadly not.

We’re struggling to decide what is actually the worst thing about this “outfit.” Is it the matching hat and dress? The bright pink tights peeking out from underneath? The hideous suede and patent toe-capped boots? If Britney can’t pull this look off (whatever this ‘look’ is supposed to be), then the rest of us mortals need to stay the hell away from pink and/or orange at all costs.

50 Shades Of Brown

When they weren’t wearing matching denim together, Brit and her ex-beau Justin Timberlake liked to challenge themselves (and fashion, by the looks of things) by wearing as many shades of brown as possible. Fans of the sitcom Friends may remember the episode where Joey’s character gets back at Chandler by wearing every item of clothing he owns—Britney and Justin’s weird idea of layering kinda reminds us of that.

The couple posed for pictures here for the release party of Brit’s second studio album Britney in 2001. But by the looks of things, they’re going to a 70’s costume party instead. JT’s sporting the kind of cringy disco flares your dad wouldn’t have even worn in college. And what is up with Brit’s cowgirl boots and fur-lined coat? In fairness, she probably had a gorgeous dress underneath...unless that was brown too.

Country Girl Chic?

It looks as if the cowgirl boots were a fave in Britney’s early wardrobe because they made another appearance here at the 2003 Kid’s Choice Awards. Brit may have been a whole two years older and wiser from the last cowgirl boot photo on this list, but she definitely hadn’t learned how to make them look fashionable yet (to be fair, who can?).

Strangely, the boots are not even the worst thing about this outfit. It’s the strange mismatch of cute and girly with try-hard accessories. The floral pinafore dress is sweet and innocent, but Brit went ahead and teemed this up with the kind of belt that Christina Aguilera wore in her Dirrty phase. If Britney was going for country girl chic with an edge, it really didn’t work out here.

Yet More Denim

Miss Spears certainly had a love affair with Denim at one point, didn’t she? At least she isn’t wearing it all over in this pic like her original and iconic denim car crash. Although, since we’re only seeing the top half, maybe she is wearing denim jeans, but let’s pretend that’s not true! Technically, this is Brit snapped at the front row of a fashion show rather than the red carpet, but it has to be included for the overwhelming irony alone.

While sitting on the front bench of a catwalk show, Brit was not at all fazed by wearing... this much denim. The newsboy cap, the vest, and the offensively-glittery necklace? It’s all a bit too much. Notice the guy next to Brit wearing as much denim as her. Maybe it’s something she curses people with if they get too close.

Sheer Black, Sheer Madness

They say, “If you’ve got it, flaunt it,” and when it came to Britney’s toned tum, she definitely had it. The only problem is, she didn’t always show it off in the most graceful way. She loved to leave her midriff bare on stage and in her music videos, but there’s something about this look that isn’t too flattering to miss Spears (or her perfectly taut belly).

Maybe it’s the fact that her dress(?) puts us in mind of some kind of nightgown on the set of a really cheap adult movie. It’s hard to know what’s more garish about Brit’s look here—the sheer polka dot sleeves, the abundance of black feathers, or the OTT makeup. Tarty isn’t a word that comes to mind often when describing Britney, but let’s face it, this looks more like a Vegas show costume than a glam red carpet dress.

Combining Snakeskin And Metallic

It has to be said. These are two materials and textures that no one would ever think to put together—like not even Nicki Minaj going to a fancy dress party. And then, along came Britney Spears. She still looks beautiful as always which is kind of unfair... and almost against the laws of fashion logic because this outfit is almost enough to give you a headache.

This is what Brit chose to wear at the MTV Video Music Awards in 1999. The good news is, she performed a few numbers on stage that night, so all the costume changes probably meant that she wasn’t sporting this outfit for much longer (but if you carry on through this list, you’ll see that Brit’s other wardrobe changes that night weren’t exactly an improvement either!).

Not So Pretty In Pink

Don’t get me wrong. It’s Britney Spears at the end of the day. She’s always been pretty (and still is even 18 years after this red carpet snap was taken). But it doesn’t change the fact that this dress now looks more than a little trashy in our eyes. Not only is the garish shade of baby pink way too Barbie-ish for our liking, but it’s the horrid fringe detail. Everything about it screams discount prom dress.

I think Brit was hoping the gigantic surfboard next to her would maybe hog the spotlight and divert attention from the overwhelming pinkness on display. Maybe we could forgive the girl, though. We’ve all made questionable fashion choices as a teenager, experimenting with colors and textures that don’t quite fit together. Britney was only 19 in this picture too. Still, it’s not as if she got more fashionable in the years ahead either...

Leg Warmers Over Pants... And Boots

Brit’s outfit is so horrendous in this photo that most people may not even realize the weird German translation of Britney’s 2002 road movie Crossroads in the background. The poster reads “Not a girl” as the title instead, probably in reference to her song I’m Not A Girl, Not Yet A Woman. But, for no one who knew this at the time, that had to look pretty strange.

Anyway, back to what’s happening in the foreground. Yikes. We’re sure Brit can pull of leg warmers in the gym or maybe when she was dancing around on stage as a little girl in the mid-80’s. But not... like this. Sparkly beige leg warmers are not a good look in any context, but over brown two-tone jeans and pointy heeled boots? Hell to the no.

Those Leggings Though...

Before we pass judgment on how awful some of these elements look together, we should acknowledge that Britney intended to make a good statement here (and no, not about the importance of dressing in a well-lit room!). She’s wearing a shirt with the words “Page Six Six Six,” and this is thought to be Brit’s attack on the tabloids and poisonous celeb coverage in the media.

Of course, she went on to make a more catchy statement about this years later with her song Piece of Me, but I guess this shirt did the job. Now that we’ve got Brit’s good intentions out of the way, can we talk about those odd leggings for a sec? Why are they under a barely-there mini skirt? As risqué as this micro skirt might have been on its own, perhaps Brit should have ditched the garish leggings altogether.

Promoting Crossroads... And Promoting How Not To Dress

Proof that even if you’re as gorgeous as Britney Spears, you definitely can’t make lime green work. Like ever. She looks as if she’s turned up to her first day at an office job, during “wear something wacky” week. Can we also talk about that bizarre style of mini skirt? Skirts and mini skirts came back into fashion throughout the noughties, and it was always tricky to strike the right balance between cute and tacky.

Unfortunately, these are definitely in the tacky category. Not only does the green-and-blue color combo remind us of bathroom floor tiles, but the skirt almost looks DIY, as if it’s been made by weaving strands of recycled plastic bags together. But if it’s not DIY and Britney actually paid something for this skirt, we hope she returned it after this was press tour.

Pink Sequin Pants

The 1999 Teen Choice Awards were a big deal for Britney. Her career was just getting started and she was crowned the winner of the Choice Female Artist award at just 17 years old. Life was looking bright for Spears (and thanks to these blinding trousers, things were looking a little too bright, if you ask us).

What did Britney choose to wear to her first major music awards show? Pink trousers that are absolutely covered in pinky gold sequins. Don’t get us wrong, Brit looks kind of cute–and far more modestly-dressed than some teen singers have dressed in recent years–but it hurts our eyes just to look at this getup for too long. We think Brit should have gone into her closet Baby, One More Time...