Celebrity Prom Night Photos Before They Were Famous
They probably wished these photos never surfaced.
Harriet King May 1st 2018 Entertainment
Prom Night is one of the most important nights of our young lives. Most of us will have fond (or embarrassing!) memories of it. Some of our younger readers may even still have it all to come; the triumph and heartbreak of finding the perfect outfit and the perfect date.
For many of us, it's the first big formal occasion we'll ever go to other than the weddings of family and friends. It's part of our progress into adulthood. We're moving on from childhood and preparing to step out into the big, wide world - and looking great while doing it.
Fashion, however, changes over time. What looked great in terms of hair and style on our prom night may not look quite as flattering many years later. You might end up wishing some of your prom night photos could stay hidden - but how did some of your favorite celebrities fare?
1. Bruno Mars
As a 'song and dance' man, Bruno Mars might be the best we've seen since Michael Jackson. He's had a string of smash hit records, made millions of dollars, and had the whole world dancing to 'Uptown Funk' just a couple of years ago. It looks like that being the new Michael Jackson may have been more a case of deliberate imitation though; he has the undeniable look of Jackson here, right down to the hair.
We can't quite work out whether the flowers we can see are some stylish flair applied to his waistcoat, or whether they're real flowers that have been draped around his shoulders. The way his date has her arms around him, it almost looks like she's trying to shield him away from the rest of the world. We don't blame her; we imagine there was plenty of competition for his affections on that evening.
2. Demi Lovato
We can see what Demi Lovato was going for here, and we're pleased to say she achieved it. We can't fault her look and her dress. In fact, the dress is beautiful. It may not be the best choice of prop - and her partner for the evening isn't up to her standards - but Ms. Lovato will have been turning heads on prom night from the moment she walked through the door.
Having your photo taken in front of a luxury car is a statement that says 'I'm a big deal.' She must have been getting practice in for all the glamorous photoshoots that she knew were going to come in her future. Not the pose that her partner has struck - he's got his arms out wide in a shrug, as if he can't believe he gets to take her out for the evening! There's nothing wrong with 'faking it until you make it' so long as you make it in the end. Nobody can deny Lovato has done precisely that.
3. Taylor Swift
Country music singer turned pop sensation Taylor Swift is undeniably one of the biggest stars in the entertainment world. She's also a poster girl for what the press like to refer to as 'Millennials,' and she's displaying the full Millennial attitude here. She's mixing pure and white prom night chic with a 'West Side' hand gesture that let us all know she's still cool and street. That's precisely the same kind of image she portrays as a pop star. She was getting her practice in early.
Wearing matching outfits to go to prom is always a bit of a risk, and if we were hypercritical we would question whether her date really needed to include that baseball cap, but then this photo isn't about him. As with the music industry in the 21st century, it's all about Swift, and she's the absolute star of the show here. Exactly as she ought to be!
4. Angelina Jolie
Many of our male readers will have grown up with posters of Angelina Jolie stuck to their walls. Jolie has been universally recognized as one of the most beautiful women in the world for the best part of twenty years, with iconic looks that have made her the female lead of many movies. She's still growing up in this picture, and she doesn't yet radiate the confidence that she'd obtain a few short years later, but you can see she's still well on her way.
As we'll see with a few of the leading ladies on our list, Jolie has chosen a prom night outfit that wouldn't look out of place at a classy wedding. Even if you weren't sure at first glance that this was a picture of her, those famous lips give it away. Looking at this picture is like seeing a photo of a friend from before you met them; you can tell it's the same person, but they're just slightly unfamiliar. This starry-eyed girl had no idea of the greatness she'd go on to achieve!
5. Ellen DeGeneres
One of the best things about being able to look at people's old prom photos is that we get a chance to see the fashions of the time! Admittedly, very few people would go to their prom night dressed like Ellen DeGeneres is in this picture. The fashion is very much 1970s, and it's never come back into style since. At the time, though, we can assure you that DeGeneres and her handsome date would have been the envy of everybody else at the ball. She's an LGBT style icon now, and she's achieved style icon status by tracking what's 'in' carefully throughout the years.
What's striking about this picture is how completely different DeGeneres looks from the way we recognize her now. If we hadn't told you who you were looking at, do you think you'd have been able to identify her? Perhaps the tartan dress would have convinced you that you were looking at a famous Scottish lady instead? Or does something about her expression give her away?
6. Tiger Woods
It's no secret that golfing legend Tiger Woods was solely devoted to his sport when he was growing up. He made his first appearance on television as a golfer before he was even ten years old. While many of us were running around enjoying our first dates and worrying out our finals, Woods was out on the golf course, working on bringing down his handicap so he could start a career as a professional sportsman. Because of that, we could forgive him if he wasn't paying close attention to fashion, but it looks like he was!
You can never go wrong with a simple, elegant suit. The edges are clean and sharp, the bow tie looks far more sophisticated than a basic one, and the decorative accessory sets the whole thing off. His date gets extra points from us for her coordination with his outfit. They look great together!
7. Scarlett Johansson
Scarlett Johansson was already a star name by the time her prom night rolled around. She appeared in 'Lost in Translation' when she was only 17 years old, so everybody knew that she was going to be a big deal in the world of cinema. Johansson didn't need to dress to impress anybody on her big night, so she went for the 'too cool for school' dressed-down look.
Dressing down when everyone around you is dressing up is a big risk to take, because if you get it wrong, you're going to stick out like a sore thumb. She had one big advantage though - she's Scarlett Johansson. She could have turned up on the night wearing a potato sack, and she'd still have looked great. She's managed to make herself look effortlessly cool, and as an added bonus she's also dressed perfectly to hit the clubs as soon as prom night kicks out. No need to bring a back-up outfit!
8. Will Ferrell
This prom night photo is hilarious, but then what else have we come to expect from Hollywood funnyman Will Ferrell? We're used to Ferrell making us laugh, and based on this evidence it seems like he started with the jokes when he was very young. He's stolen his date's tiara for his official photograph. In a weird way it works for him too, he looks almost angelic!
His date seems to have taken it in good grace, as well; it was probably an essential part of her look for the night, but she's been covered in flower leis, so she has other accessories to fall back on. What happened to Ferrell's jacket, though? Did he accidentally leave it at home? More importantly, did anyone switch their vote and declare him Prom Queen? If he's going to wear the tiara, he might as well put himself in the running!
9. Michelle Obama
The last thing we want to be accused of is political bias on this website. You've seen how Republican Sarah Palin looked on her prom night. Now let's take a look at former First Lady of the USA and wife of Democratic President Barack Obama, Michelle Obama! And we guess that relations between the two women must have been good at the time, because Palin has even let her borrow that wicker chair that was in the background of her own photo.
We're not absolutely convinced that the chair should have made it into the shot, because it's the same color as Obama's dress. The dress probably looks spectacular against a slightly better background. She must also have had a hard night of partying, because she's had to take a seat while her date (who looks a little like Richard Pryor) waits for her to get her breath back. Something about that level, cool gaze in her eyes is letting you know that she's going to be a very big deal one day.
10. Brad Pitt
There was a famous song in the charts a few years ago that went by the title 'Acceptable In The 80s.' That's the exact phrase we'd use to describe the suit that Hollywood legend Brad Pitt is wearing in this picture. You might turn your nose up at it now, but back then it would have been considered the ultimate in cool, and you'd have considered him just as attractive as everybody does today!
We admit that if you're planning your prom night right now, you'd probably avoid wearing a jacket that clashes with your trousers. This was the time of 'Miami Vice,' though, and that's what went on all the time. This look is difficult to explain to those who didn't live through the era, but please take our word for it that Pitt was the man back then, and is still the man in the here and now!
11. Britney Spears
You can tell from these pictures that Britney Spears has worn the last 20 years of her life very well. You can also tell that red is really her color. That doesn't surprise us - we still remember the video to 'Oops, I Did It Again,' but it's remarkable that she's been able to maintain so much of her youthful appearance over time. The younger Spears, in case you can't tell, is the one on the left. At the time this was taken, she'd have been well on her way to stardom via the Disney production line.
The neckline of her prom dress might be a little daring for a girl of her age, but very soon after this she'd be dressed as a schoolgirl for 'Baby One More Time,' so we guess that's just the way the wind was blowing for Spears back in those days! At least the shape of the dress would have given her plenty of movement to dance - and we all know how much she loves to do that.
12. Jessica Alba
Here's another prom night couple who decided to go for total color coordination! It's sometimes a little difficult for a woman to match a man's colors if he goes for basic black and white, but Jessica Alba has managed to do it here. Yes, the style is very 1990s, but the 90s were a quirky time. She's taken all the best aspects of a maid's outfit - which is just a little bit risque - and turned it into something less cliched. It's a unique and striking look, and we like it.
Alba's date has also forgone the traditional, choosing to go with a suit that has a white trim and lapels, as well as a white shirt. Nobody else on the evening will have looked anything like this couple, and we suspect that was the point. You're never going to be crowned Prom King and Queen if you don't stand out! Alba sells the look perfectly with her trademark superstar smile.
13. Jimmy Fallon
Given how slick he looks these days, this might be a little difficult to believe, but yes, that really is famous talk-show host Jimmy Fallon. You can see it in his smile. The suit might not be as expensive as the ones he now wears every week on television, but all the building blocks that made him who he is today are still clearly there in this picture. We'd say that this was taken in either the late 1980s or the late 1990s - the time of big hair and big accessories!
Fallon's date is in danger of stealing all of the attention in this photo, but we have no problem with that. Prom Night tends to be a bigger night for the ladies that it is for the men, and she's gone to the next level with her outfit. Fallon could afford to stand aside for one night and let somebody else have the spotlight. After all, he'd be seeing plenty of it himself in the future!
14. Julia Roberts
We might have mentioned this earlier on, but the 80s were a time of outrageous fashion. When we say outrageous fashion, we mean seriously big hair. Even taking that into account, most people would never have been able to achieve the kind of volume that Julia Roberts is exhibiting here. It's almost bigger than she is! That's in no way meant as an insult; she looks delicate, petite and feminine in her black dress.
Roberts' beautiful smile her always been a big part of persuading audiences to fall in love with her in her movies, and she obviously had it mastered from an early age. You'll rarely go wrong pairing a little black dress with an elegant accessory, and Roberts has smashed that brief with the elegant pink butterfly that's attached to her bag. What a Pretty Woman!
15. Kelly Pickler
Country music and television star Kelly Pickler certainly knows how to dress to impress. The one-time 'American Idol' singer is demonstrating that in the image on the right, which has been taken on the red carpet. She looks stylish and graceful. We wouldn't immediately have known that the younger woman on the right was also Pickler, but we have absolute confirmation that it is. What a transformation!
When we're young, we often dare to bare flesh on a level that we might shy away from a few years later. Pickler clearly knew she looked great, decided she was going to flaunt what she had while she still could, and turned up for her prom wearing a dress that's barely there at all. 'Daring' doesn't even begin to cover it. We'd go so far as to call it 'defiant!'
16. Lizzy Caplan
Lizzy Caplan is a versatile and charming actress. She was the star of 'Cloverfield,' and also had a prominent role in the high-school comedy 'Mean Girls' with Lindsay Lohan. She may have known a thing or two about mean girls during her life at school, because it looks like she was one of the 'alternative' kids. It was all about Limp Bizkit and Linkin Park when Caplan was in her teens, and based on this picture she threw herself into that lifestyle.
Many of us went through an alternative phase when we were younger, be it 'goths,' 'emos' or whatever the term of the time was. It's sometimes nice to have a collection of pictures of ourselves from a time when we didn't care what anybody else thought of our clothes, and we could push the boundaries without fear. Caplan may not have won the conventional Prom Queen title, but if there was an alternative Prom Queen for the evening, it was definitely her.
17. Matthew McConaughey
Wait, wait, wait. Matthew McConaughey, we need to have words. These photos were taken around twenty years apart. Can you please reassure us that you're not wearing the exact same suit in both of them? It's certainly a very close visual match, right down to the slightly shiny lapels. Famous people aren't supposed to wear the same outfit twice. If he's been hoarding entire suits for his whole adult life, how big is this man's wardrobe?
To many people, McConaughey is the epitome of a stylish southern gentleman. He's well mannered, and always looks clean and sharp. You can sense the makings of such a man in his prom night picture; he looks a little older than his years, but then at the same time he's still very young in his facial features! He gets extra marks from us for choosing the blue bow tie to match with his date's prom dress. That's a classy move, McConaughey. No wonder everybody likes you!
18. Ryan Seacrest
Ryan Seacrest is a man who knows a good suit when he sees one, and also knows how to wear it well. He might still have been trying to master that skill at the time his prom night rolled around, but he gets more right here than he gets wrong. We think the suit might be a tiny bit too big for him, but then baggy clothes were more fashionable in the 1990s than they are now. It's one more look we can put down to the era's style.
Taking that into consideration, we won't mark him down for his outfit. We will mark him down for the way he's posing with his date, though. Note the position of her hips, and then the position of her head. She's twisting one way with her body and the other way with her neck. Only owls are supposed to be capable of that degree of neck rotation. There's no way that could have been a comfortable pose, so well done to her for managing to smile her way through it.
19. Snoop Dogg
Who would ever tell Snoop Dogg they had an issue with what he was wearing? Would you? If so, feel free, because we're not going to do it! Based on this picture, we don't think we actually have to anyway. Snoop looks great! It's not often we get to see the rap superstar wearing a suit, but perhaps he should consider giving it a try more often. He's gone for the classic look, and he's pulled it off with aplomb.
His date is clearly impressed with him; look at how broadly she's smiling! She's gone to special effort to make sure she's matching his look as well, right down to the flower accessories on her wrists. The least Snoop could do is smile for her. Come on, Snoop, you both look fantastic. Let your face know about it!
20. Carrie Underwood
Well, here's Carrie Underwood giving the 'Rachel from Friends' look a try. We think she rocks it! We're just a little sad that we only have this grainy black and white photo to judge it by. We hope she didn't destroy all the evidence from her prom night. Everybody had 90s hair once, and Underwood doesn't have to be ashamed of it!
The photographer has done Underwood something of a disservice here. This picture should all be about her - it's her big night, after all! Instead, her date dominates the scene, pushing her to the fringes. Maybe there are better photos of this evening somewhere within the Underwood household, safely under lock and key so people like us can't get our hands on them!
21. Ashton Kutcher
There is absolutely nothing worse than having someone take a picture of you on a night out when you're dancing, and not knowing the picture is being taken. We have all lived the nightmare that Ashton Kutcher is going through here. Unlike Ashton Kutcher though, most of us look like complete fools in such pictures. He actually, somehow, manages to get away with it. Maybe it's those good looks that would go on to seduce Demi Moore.
We suspect, given the dancing and the way that only one button of his waistcoat is done up, that this picture might have been snapped several hours into the evening. If Kutcher lost half his outfit, danced the night away and laughed and joked with the girls in this picture, then we bet he had a great prom night. Good for him!
This is a classic 'before they were famous' picture. You only need to take one look at the photo to know you're looking at Beyonce Knowles, but it takes a couple of seconds more than that for it to dawn on you that she's not quite famous yet. She's attractive and striking, but the slight refinement that came with her fame just isn't quite there. Even if she is absolutely owning that dress!
It's a risk to go out to a big occasion wearing a dress with an unconventional cut. It can hang in the wrong places, show more or less than you really wanted to or just generally let you down. For Beyonce, it worked perfectly. The patterning on it is on-point for the mid-1990s, and her date looks like he can't believe his luck to be standing there with her. We're not sure she's as thrilled though; check out how awkward that hand-holding is.
After reviewing the evidence here, we have to ask a very serious question. Is 'Black Eyed Peas' singer Fergie a time traveler? We're forced to consider the possibility because these pictures were taken twenty years apart, and yet she looks younger now than she did back then. We don't just mean in her physical appearance either; we're talking about the way she dresses.
When Fergie broke out into the music scene, she was presented as an up and coming artist from the streets. Her prom night picture is worlds away from that image. She's dripping in expensive-looking jewelry, she has immaculate long white gloves on to compliment her debutante dress, and she's carrying flowers. She looks like British royalty attending a high society dinner. If we didn't know any better, we'd have thought it was a picture of the other 'Fergie'; the former Duchess of York!
24. Kim Kardashian
Like Carrie Underwood, Kim Kardashian seems to have tried to rid the world of the original copies of her prom night pictures. All we're left with is this badly-scanned black and white memento of her big night. We know what you're thinking as you're looking at this, but we can tell you with certainty that yes, that really is reality television superstar Kim Kardashian.
It's no secret that Kardashian has had more than a little 'work done,' but the full scale of that work doesn't hit you until you see a picture of her natural look. She barely even resembles her younger self anymore. That's a shame, because she was undoubtedly a pretty girl. The eyes, the nose, and the lips have completely changed since this was taken, and she'd never be seen dead with that hairstyle now. Despite that, this picture serves as a reminder that Kardashian was once like the rest of us, and as excited about her prom night as we all were!
25. Lady Gaga
Who needs to dress up for prom night when your mission for the evening is 'just dance?' Lady Gaga was a few years short of becoming a global music and fashion icon here. Based on her habit of wearing truly outlandish clothes both on and off stage, you probably expected her to push the boat out for her prom night. Instead, she went in the opposite direction. That was good news for her date, who likely wouldn't have looked as happy to see her if she was wearing a dress made of meat.
Between the light blue strappy dress and the sunglasses, this shot looks more like it came from a summer holiday than a prom night. It's only the presence of her date's suit that gives the game away. Wearing shades indoors is the ultimate celebrity cliche, so it seems Gaga was dressing for the lifestyle she wanted long before it became a reality.
26. Natalie Portman
We have a lot of time for Natalie Portman. She's one of the coolest actresses in Hollywood, and she's really made us laugh with her appearances as a rapper on 'Saturday Night Live.' She's regarded as a princess by 'Star Wars' fans, and she's the epitome of a 'cool mum.' It's a real throwback to see her looking so young on her prom night; we know how old she must have been, but she looks around 14, and nervous. We want to reach back and tell her not to worry; everything's going to turn out great!
At first glance, it looks like she's gone for the two-tone approach, but we think she's just covering her ball gown up with a separate top to keep herself warm before she enters the dance. We see the tan lines a well, and we absolutely feel her. We've all been there! We hope she eventually shook off the nerves and had a wonderful evening.
We didn't really expect Jersey Shore's Snooki to appear ultra-stylish on her prom night; it's hardly what she's known for! In fact, we'd say that Snooki who lives by the motto of 'what you see is what you get.' What we get from Snooki's prom night photo is precisely what we expected to see, and she wouldn't have it any other way!
Like Ashton Kutcher's picture earlier on, we think this may have been a 'late in the evening' snap. We're basing that off the jaunty angle of the sunglasses, and the poses everyone is striking for the camera's lens. Snooki is getting some excellent party practice in ahead of her 'Jersey Shore' days; although by the standards of a 'Jersey Shore' party we're not sure that a standard prom night would even have counted as a warm-up.
28. Tyra Banks
If a prom night photo of Tyra Banks existed, it was always going to make it onto this list. She's the woman who's taught millions of others how to turn, pose, wear a dress and look great for the camera! She hasn't quite nailed her signature pose in this picture, but she's well on her way towards it. Her choice of dresses has already made the grade. It's the perfect balance of stylish and sexy.
We've seen less awkward pictures of couples standing together, and we're not sure why both of them are frowning, but perhaps they were doing for the sultry and sulky look, which would be in keeping with the dark hues of that ultra-early-90s color palette around them. If you were shown a picture of Banks at this age and asked to guess what she'd be when she grew up, you'd probably have made 'model' your first or second choice. Some people are just born to do it.
29. Sandra Bullock
Sandra Bullock is obviously another celebrity who's mastered the art of time travel. She looks so similar now to the way she appears in this photo that you could be forgiven for thinking it's a candid photo from her wedding, and that this was the first dance. It's nothing of the sort. This is a black and white still from Bullock's prom night, and she looks like she's having the time of her life!
We're not quite as convinced her date is having as much fun. To us, it looks a bit like he's just leaned in for a kiss and been turned away. Oh well; he should be happy that he got to dance with her. Even if she is holding his thumb rather than his hand. As for her hair; that's full on 'Xena: Warrior Princess' - an icon of the time!
30. Reese Witherspoon
So, it turns out that Reese Witherspoon has been lying to us this entire time. She's spent most of the past two decades as one of the best-known blondes in Hollywood; her hair color was even one of the central points of the 'Legally Blonde' movies she starred in. As this picture proves, though, she's never actually been blonde. She's a brunette.
As well as being a brunette, it looks like Witherspoon was a late bloomer. She looks about twelve in this photo! The style of dress, with what looks like a t-shirt covering her cleavage, is the kind of thing you'd dress a younger child in as well. We imagine she was still having to carry her passport to bars with her to order alcohol until she was almost 30. You know what they say though - if you look 20 when you're 30, you'll look 30 when you're 50!
31. Adam Levine
You've got to be an absolute superstar to pull of an all-white top-and-tails look. It's a big outfit that calls for a big personality. It's just as well that the man wearing it is a rockstar. He may not yet have the beard or the tattoos, but that's Maroon 5's Adam Levine. It doesn't look like 'this love has taken its toll' on him either; he looks positively delighted to be standing there with his date.
Our only reservation here is that it looks a little warm. White isn't a good color to be wearing when the sun is beating down on you! It's to be hoped both Levine and his partner were able to find some shade when they went indoors. We might associate the all-white look with purity - something that we don't always readily associate with rock stars - but Levine looks cherubic here.
32. Blake Lively
Here's Blake Lively exhibiting the kind of prom night look that would surely have caused some gossip, girl. It's not uncommon for a girl to go for the Disney princess look for prom night, but the combination of the tiara and the sparkly pink dress is really pushing that idea to the max. She was brave with the way that it was fitted around her shoulders, too. We hope she didn't do too much enthusiastic dancing, or she may have suffered a wardrobe malfunction!
One of our favorite things about many of these photos is how awkward some of the dates look. The gentleman in this picture is a perfect example. He's happy to be photographed with her, but he's so unsure of himself that he can't even bring himself to put his arms around her or even touch her shoulders. Instead, it looks like he's measuring her for a suit. As for her - have you ever seen an expression more carefree?
33. Jon Hamm
As characters go, they don't come much smoother talking or looking than Don Draper, as memorably played by Jon Hamm in 'Mad Men.' Draper is the sort of salesman who could persuade you to buy sand in the middle of a desert, and has the kind of finely-tailored look that oozes sophistication and class. Based on this photo, Hamm was already in training for the part from his teenage years onward. Most boys on prom night look like kids in their father's suits. Hamm doesn't.
He hasn't quite got the million-dollar smile down yet - that will come with time - but he's clearly happy to be posing for pictures with his date. They've even managed to hold hands without it appearing to be awkward. That's how it's supposed to work! We can always rely on Hamm to show everybody how it's done - even if he wouldn't buy anything from him.
34. Halle Berry
Wow, Halle Berry. Wow. And we mean that in the best possible way. This is an absolute jaw-dropper of an outfit. If the internet had been a thing back then, this would have broken the internet long before Kim Kardashian ever tried it. The Hollywood screen icon truly looks like royalty here.
We think we know where she got the idea from - a lot of young girls growing up in the 1980s saw Britain's Princess Diana as a style and fashion icon. Berry seems to have taken 'the Diana look' and made it her own, right down to the hair. We wish we had a clearer picture than this grainy image - which might have been taken from a yearbook - so we could give it our full appreciation. We hope that she still has a few mementos of the evening laying around at home somewhere. Absolute Queen!
35. George Clooney
We would recognize that jawline anywhere, George Clooney. Even if you're wearing the most 1980s of all 1980s suits, and you've gone with the most dreaded hairstyle of the era, too! The 'business out front, party out back' mullet was briefly the must-have haircut of the decade. If any man had the looks to carry it off, it was Clooney, and to our shock, we have to concede that he's done it!
It's easy to point and laugh at the white suit and the hair, but ultimately that's still the man who most people feel is second only to Brad Pitt in terms of looks during the past twenty years, and the outfit was of its time. Style changes, class is permanent. Clooney is permanently classy. We can tell that his date definitely agrees with our assessment. She'll cut off the circulation to his shoulders if she grabs them any harder!
36. Lindsay Lohan
You probably think you can picture what Lindsay Lohan looked like when she was attending her prom night. After all, she was very young when she was in 'Mean Girls,' in which she played a bratty high-school kid, so how far from the truth could the portrayal be? Well, if this image anything to go by, very far indeed.
Instead of dressing up for prom night, Lohan dressed down. Like Scarlett Johansson, she was already starring in movies by the time she reached prom night, and so she probably didn't feel the need to dress to impress anybody but herself. It's a little hard to follow this picture, because everyone's stood at an odd angle, but once your eyes adjust to it, you'll see that she's actually wearing jeans. She'd already made it; she didn't need to go over the top with a ball gown to prove it!
Rap stars didn't come much more stylish than Usher during the late 90s and early 00s. He never seemed to put a foot wrong - even when he went as far as trying an all-white look for his prom night. 99% of people couldn't get away with this outfit in their wildest dreams. Usher is not 99% of people. He's in that top 1%, and he's styling it out here!
His date has risen to the occasion too, with a sleek red dress that matches his rosette. They look like a great couple, but they might have been caught in the middle of a debate here. Neither of them appears to be too happy about being photographed. Also, is it us, or is there a rip down the middle of this photo, like it's been torn apart and then put back together? We hope their evening together was a happier one than this image seems to suggest!
38. Kobe Bryant
We understand that basketball players aren't like us regular humans. They're all giants, with oversized bodies. They can't just walk into an average store and buy a suit off the rails; chances are they need to find a specialist venue, or have something specifically tailored for them. Kobe Bryant probably struggled to find an outstanding outfit to go to prom in; especially during his pre-fame years when he couldn't just pay one of the world's greatest tailors to solve the problem for him.
Considering all of the above, he's done just fine here. If you're in doubt, always go for the classic look, and you'll be in no danger of embarrassing yourself. He's also sending the world an early statement about how cool he is by passing on a tie. Ties sometimes feel like the most unnecessary garment of them all, and if you can play it off like Bryant, then why should you bother with one?
39. Faith Hill
One of two things is true here. Either country music star Faith Hill decided she was going to be so extra on her prom night that she was going to have two posies of flowers; one to carry and one to pin to her dress; or she's already been named Prom Queen for the evening, and the second posey is her reward. If that was the case, we wouldn't be surprised. She's gone for a flowing and elegant design which is both simple and sophisticated. No wonder her date looks overjoyed.
The picture looks a little bit like a wedding picture - and he probably wishes it was - but this is a really nice memento of what was hopefully a lovely evening for both of them. Also - at the risk of being harsh - it never hurts to have a slightly less good-looking date, so you stand out even more. We commend Hill on her strategy!
40. Elizabeth Banks
If it weren't for the picture on the right to confirm it, you probably wouldn't have guessed that this was a prom night picture of 'Hunger Games' star Elizabeth Banks if we'd given you ten guesses. Everything from her hair color to her smile has changed beyond all recognition over the years. She still manages to look classy and beautiful, but she's rocking a completely different look and style.
If Banks was given a chance to go to her prom night again, we've got a feeling that she'd vamp it up and really go for the 'big dress, big hair' look. We don't think she would need to. It might be worlds away from how we're used to seeing her, and a little girlish, but there's no denying that Banks was a cute teenager. The slightly quirky dress that doesn't quite know how many shoulders it wants to be on is working for her here, too.
41. Courteney Cox
Earlier on, we said that we suspected both Fergie and Sandra Bullock of being time travelers. If she is, it would appear she's let Courteney Cox in on the secret. We just can't get our heads around the idea that it really is the 'Friends' stay in the picture on the left. It looks like a photo of her mom and dad, taken somewhere around the 1960s. Everything about the photo from the black-and-white image to the hairstyles comes from an era decades before this was taken!
Nobody says you have to bare all your flesh on a prom night; Cox obviously decided she was going to go with the conservative look. It's hard to tell from the black and white picture, but we think she made it work for her by contrasting two different tones in the outfit. Plus, that smile would stand out a mile no matter what she was wearing.
42. Debra Messing
What is it with all these time travelers? Do we have to add Debra Messing to our list now, too? If anything, she looks younger now than she did on her prom night! That's not a sleight against her prom night photo either; she just looks fantastic for her age. Looking at the image on the left though, we have to wonder if she went to the same school as Courtney Cox. Perhaps they even lived close to each other, were best friends, and swapped fashion tips. They've ended up going for the same outfit strategy.
Again, we feel like we might be losing the finer details of this outfit to the black and white picture. It looks like it's all white, but it's also possible that it's a combination of white and another light color. The overall style of the dress is 70s, but the shoulder pads just scream 80s, so this is Messing bringing two eras together!
43. Bella Thorne
Bella Thorne is not, never has been, and probably never will be someone who plays it safe with her fashion and outfit choices. She's bold enough to strike her own path, and she does it with style. You can tell from the image on the right that she's confident with her figure and unafraid to show herself off in loud colors. It would seem that she was no different on her prom night, when she took the Disney princess look to a whole new level!
There's a surprising difference between the pictures, given that Thorne is still a mere 21. Prom night is a recent memory for her! She's been a familiar face to us since she was a child, so like Scarlett Johansson and Lindsay Lohan, prom night was probably a little dull as they'd have been to far bigger parties in the past. Unlike the other two ladies, though, Thorne put in the effort with her dress and her look. Her date seems to appreciate it - although she could at least have looked at him!
44. Kerry Washington
Kerry Washington obviously had a great prom night in her sparkling dress, but did this picture take her by surprise? She looks shocked to have been approached by the gentleman behind her, although he looks somewhat suave and debonair. We can't help wondering whether he was the date she came to the part with, or the one she ended up leaving with instead!
Given the lack of activity going on in the background, we'd say this photo was taken towards the end of the night, and Washington and her man have seen prom night through to the bitter end. That's the way it's supposed to be done - it's one of the nights of our young lives that we never really want to end. We hope all of our readers looked as happy at the end of their prom night as Washington seems to be in this moment.
45. Kevin Garnett
When we talked about Kobe Bryant earlier, we discussed the limitations that being tall can place upon your choice of outfit. Kevin Garnett appears to have found a way around those limitations. He's playing a little fast and loose with how wide those trousers are - they wouldn't look out of place in MC Hammer's wardrobe - but he's pulling the luck off with confidence. Full credit for the coordination with his date's outfit, too.
We can't help but smile at the pose here. Dating a basketball player is always going to lead to major height differences for most couples, but the way Garnett's cummerbund matches with her dress makes it look like it's part of one and the same outfit, and he's carrying her around with him, physically attached at the waist! They make for a cute couple.
46. LeBron James
Gray suits can be cool. Especially on a prom night, where everyone is likely to wear black (other than the ill-advised souls who make the sometimes -regrettable decision to wear white), the color can make you stand out. The key to carrying it off is picking a high-quality gray suit with some style and flair. LeBron James has done it here. He must have found a local tailor who'd worked with basketball stars before, because that suit is perfectly fitted to his huge frame. Great work!
We love seeing pictures which show that a couple has made an effort to coordinate their look for the evening. James and his date have taken the subtle approach of having matching rosettes, and they look all the classier for it. She's a queen of 90s style, and we're sure James was very proud of having her on his arm that night!
47. Meryl Streep
First off, congratulations to Meryl Streep. Based on this picture, it would appear that she and her date for the evening were voted as prom king and queen! We assume that's the case anyway, because otherwise we're not clear on why they're taking a walk through the gardens with an audience, and she's wearing a tiara. If we're right about them winning, it's the ultimate vindication of Streep's bold choice of dress.
A few of the style choices on this list were products of their era, and this is another one. It would have been the 1960s when Streep went to prom, and dresses like this one were all the rage. We shouldn't hold that against her; we imagine it was quite a common look on the night. She looks like a hippy and a flower child; perhaps she was in training for the summer of love, which was right around the corner!
48. Sarah Palin
We don't expect politicians to be style icons, but then Sarah Palin is (or should that be 'was?') quite an unconventional politician. She brought a touch of glamour to her role as Governor of Alaska; a touch of glamour which is also present in this picture. Knowing how far to go with dressing up for prom night isn't an easy decision to make. She's gone for 'less is more,' and it's really paid off for her.
It's no surprise to us that a conservative woman would go for a conservative dress, and there's a lot to be said for her selection. It's a simple, elegant ball gown that suits her and works for the occasion. We're a little less sure about her date, who appears to be dressed as a snooker player. Maybe that's why this picture is another one for our collection of people holding hands awkwardly!
This might be hard to believe for some of our younger readers, but there was a time during the 1990s when every fashion-conscious guy had curtains as their hairstyle. That parted, floppy fringe was the look that every guy tried to grow out, and every girl went crazy for. If you could pull it off, then you too could have the pick of the girls as your prom date. Even if that girl was future pop star, Rihanna!
She may have made her name as a 'rude girl,' but Ri-Ri looks anything but rude here. In fact, she looks quite shy and demure. She certainly knew how to dress for the occasion even back then though - she's managed to pick a dress that blends in with the decor of the venue. We wonder if she was using it as camouflage to hide from her date on the dance floor?
50. Jennifer Aniston
A Prom Night dream and a beauty queen! We bet competition to be Jennifer Aniston's date for the evening was fierce. Even back then she was a strikingly attractive young woman, and she'd surely have been in the running for Prom Queen on her big night. Her prom night date probably still dines out on the story.
There was a time when her 'Friends' era haircut was so popular that every teenage girl wanted it. They could walk into their hairdresser's salon and ask for 'the Rachel.' This hairstyle isn't quite 'the Rachel,' but even at this tender age, it's clear that Aniston was on her way to a lifestyle of looking fantastic. Her look is on point for the fashion of the era, and you can rarely go wrong with a flowing black dress. Our only issue is that some might say she even looks better now!