High school is an awkward time for everyone. Unless you were some kind of sports star or the head of the cheerleading squad, or at the very least in with the right kind of popular people, chances are those years were filled with cringe-worthy moments and some heaping helpings of insecurity.

Even if you were somehow at the top of the pyramid, you probably weren’t immune to all of those doubts and worries, and you probably looked at the posters of celebrities you had on your walls and wondered what it would be like to be as cool as them. The reassuring news is, they were probably just as awkward and uncomfortable in high school, and the best evidence out there are there prom photos!

20. Lady Gaga

Lady Gaga is one of the biggest stars in the world and, at the Met Gala this year, she also proved that she was one of the most fashionable. However, she has made some pretty questionable fashion choices over the years, from heels so high she fell over every time she took a step, to the infamous meat dress.

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The funny thing is, maybe her worst fashion moment ever came from before she was famous. This prom dress is hardly fashion roadkill, but it is far more bland and normal than we’re used to seeing from the Queen of pop, and that make-up is pretty questionable too.

19. RuPaul

RuPaul is another person famous for his outrageous fashion. He spends most of his days in printed suits so brightly coloured that they’re hard to look at, and when he’s not wearing those – he’s wearing a full face of make-up, a floor length cocktail dress, and a lace front wig.

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I’m not sure if RuPaul was told he couldn’t go to prom in drag, or if he just didn’t want to, but either way he didn’t settle on a great option. Though it’s cool he was brave enough to wear make-up, and his date looks like a fairy queen, his outfit just makes him look like a Tim Burton character.

18. Courtney Cox

Most people know Courtney Cox as the uptight cook with a heart of gold from Friends, where she takes second place behind Jennifer Aniston as the most fashionable woman in the cast. Despite that, she went on to have a pretty successful modelling career in her own right.

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Her reputation as a stylish person only makes it more surprising that she went to prom in a vest dress with a sweater underneath it, with some kind of bizarre name badge on it to boot.

17. Blake Lively

Blake Lively is famous for being one of the most beautiful women in the world, and there’s no denying that even in her prom picture, she looks absolutely adorable.

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With that said, there’s no getting over how brilliantly tacky this pink sequin dress is, especially since it’s got a band of floral silver sequins over the pink. Not only is it pretty ugly, but it also looks like it would be super uncomfortable.

16. Beyonce

When it comes to fabulously stunning pop stars, there’s no debate about who is in the top spot. Beyonce is famous not only for her incredible voice and amazing dance ability, but also her cutting edge fashion.

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To be fair, Beyonce looks beautiful in her prom picture, and her minimal make-up and slick hair hold up pretty well. The same can’t be said for that spiral print prom dress with the oval cut-outs though, as that’s not one of her fashion high-points.

15. Natalie Portman

Natalie Portman is another celebrity so timeless looking that she manages to look gorgeous no matter what she wears, and to be fair, the dress she decided to wear to prom is actually pretty blameless.

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The reason this look ended up on the list is that Portman clearly hadn’t learned to be comfortable in front of a camera yet, and she looks as though she was forced to take this picture by her parents, when she just wanted to leave and get to prom already.

14. Jennifer Aniston

When it comes to the nineties, there are few style icons with more sway than Jennifer Aniston. Her iconic looks on Friends had every nineties chick tuning in to copy her, and her unique layered bob started a trend that lasted for a full decade.

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However, Aniston hadn’t figured out her signature haircut by the time she went to prom, so instead we get a super eighties looking bob that looks like its more backcombing and hairspray than actual hair. She does look happy to be there though, which is nice.

13. Reese Witherspoon

Now, compared to some of the other looks on this list, the dress Witherspoon chose to wear to prom is actually pretty tasteful. With that said, the trend of wearing vests under dresses for formal events is one that isn’t coming back any time soon.

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Not only that, but something about the way she chose to wear her hair scraped back makes her look super startled in the picture, and the super dark lipstick isn’t helping either.

12. Scarlett Johansson

Scarlett Johansson is an accomplished actress who has played a whole host of iconic roles in the past, but she’s also super passionate about fashion. She loves androgeny and edgy looks, and has done a bunch of photoshoots where she owns that aesthetic.

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However, if you want to see her tackle that vibe way less successfully, it’s worth looking at her bizarre prom look, which involves blue eye shadow, hoop earrings and a men’s shirt with a diamond necklace. No part of this look aged well, and she’s even abandoned the nose piercing since.

11. Shane Dawson

Most of this list focuses on women, but that’s only because women’s fashion changes far more rapidly than men’s – so men have a much better chance of wearing something they won’t look back on and cringe. Shane Dawson just got the short end of the stick.

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Though Dawson has said he was super unhappy at the weight he was as a high schooler, the bigger issue is that haircut, which is somewhere between a classic emo/scene cut and just completely out of control. Not only that, but the suit doesn’t fit, and his tie is way too skinny.

10. Jeremy Renner

Jeremy Renner is a super nice guy, but you’d never know that from looking at his work. He’s pouting in almost every model shoot he has ever done, and he has a knack for playing either stoic characters or straight up villains.

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The good news is, he’s smiling in his prom picture. The bad news is, he has the weirdest mullet on record, and the pink and all-white suit isn’t exactly fashion-forward either.

9. Michelle Obama

Michelle Obama is one of the most aspirational women on the planet. She has multiple degrees, she has done huge amounts of charity work, and as the First Lady of the USA she implemented multiple initiatives to make people’s lives better. Not only that, but she’s super stylish too.

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Unfortunately for her, she probably didn’t know the powerhouse she’d become when she took her prom pictures. Otherwise, she might not have chosen a silk blazer and high-slit dress combo, and she probably wouldn’t have posed in a wicca chair like it’s some kind of woven wooden throne.

8. Barak Obama

Likewise, former president Barak Obama is probably one of the coolest people on the planet. As well as being super intelligent, he’s also genuinely kind and funny, not to mention fashion-forward and slick in his own understated and presidential way.

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With that said, there are some weird choices being made here. Why is he wearing a white jacket with a dark blue shirt and a light blue paisley tie? Why does he have a garland of leaves around him? Why does he have two dates?

7. Amy Poehler

Amy Poehler is a comedian, so she has more licence than most female celebrities to look ugly or goofy. Even so, she’s got a reputation for being glamorous and put-together, at least in a kind of relatable and wholesome way.

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The issue with her prom photo is that she kind of looks like she’s showing up drunk to her own wedding, or being roped into being a bridesmaid at a wedding she doesn’t really care a lot about. That, plus the fact that the dress looks retro in a really bad way, makes this a prom photo she’d probably rather forget.

6. Ellen DeGeneres

Ellen DeGeneres is not a dresses and skirts kind of person, there’s no denying that. However, she’s a TV personality with her own slick and put-together fashion sense, which often involves her looking cool and stylish in awesome suits and blazers.

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She obviously hadn’t realised that keeping away from dresses made her feel more comfortable by this point, and so she opted for this gingham-print shirt dress for prom instead. Not only is the colour eye-popping, but it’s weird seeing her without her signature pixie-cut, and she just doesn’t look very happy with her choices.

5. Rihanna

Rihanna is one of the most fashionable people on the planet, to the point where she’s almost as famous for her red carpet looks as she is for her music. Not only that, but she has a highly successful lingerie and make-up line, meaning she’s even an authority on fashion and beauty for others.

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When you take that into account, it’s not surprising that she actually looked pretty good at her prom, with a dress that looks dated now, but is simple enough to go end up fully in cringe territory. Instead, this look is on the list because of how far she’s come since then, and how she probably looks back on this in dissapointment.

4. Will Ferrell

Will Ferrel is the kind of comedy actor who loves making himself seem dumb, annoying or unattractive – sometimes all three in the same movie. That means we don’t tend to see him as a heartthrob or a romantic lead, even if he’s undeniably kind of handsome.

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The same can be said for his prom picture – he seems to be going for funny and dweeby rather than handsome, hence the mini tiara and the uncomfortable look. With that said, there’s no getting over the fact that he kind of looks like Ryan Reynolds, which is a definite plus.

3. Taylor Swift

Taylor Swift is another pop star who has a reputation for being stunningly beautiful, even if her red carpet looks have always been a little on the pedestrian side. She’s started to branch out into more edgy and high fashion looks recently, but that definitely wasn’t true of her in high school.

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Not only is she a million miles away from her natural porcelain complexion, but the dress looks kind of cheap and boring. That, plus the seriously early-2000s minimal make-up and fried hair, and this probably won’t rank highly on a list of her best fashion moments.

2. Jimmy Fallon

Jimmy Fallon is another celebrity for whom fashion doesn’t really factor into their day to day life and career. It’s obvious that he knows how to wear a nice suit, but that’s kind of as far as it goes when you’re a late night chat show host.

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Wearing a nice suit isn’t that difficult of a skill to acquire, and even his prom suit isn’t that bad. The bigger issue is that he kind of looks like a vampire, and he’s letting himself be completely overshadowed by his super eighties date in the sparkly nylon stockings.

1. Brad Pitt

For a while in the early nineties, Brad Pitt was considered one of the most handsome men in Hollywood, and there was definitely a reason people thought that. He consistently shot ad campaigns for fashion and perfume brands, and he even had his fair share of magazine covers.

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That makes him the perfect candidate for a “See? Even they weren’t cool in high school!” list, since he definitely didn’t come into his own until later on. Part of that is to do with the baggy, ill-fitting suit, but it’s actually the horizontally striped tie and the mullet that are the bigger problems.