Awkward Prom Photos and Celebrity Prom Outfits

Awkward Prom Photos and Celebrity Prom Outfits

Prom is one of those occasions in every young American person’s life that is monumental and memorable. Hopefully for the right reasons. Countless Hollywood films have been made with a prom featured as the highlight of the movie. She’s All That, American Pie, 10 Things I Hate About You and Pretty In Pink to name but a few. For women, in particular, it is a chance to buy a pretty dress and get dolled up to the nines by having their hair done, makeup fixed by a professional and their nails painted at a salon.


The queen of the charts went to High School in her hometown of Texas and was as gorgeous as a tennager as she is today. She was in Destiny’s Child at the time this photo was taken, when they were a four piece. She went on to become one of the most famous women on the planet and is now mother to three kids, including a set of twins. She is married to fellow music maker, Jay Z and the pair are thought to be collectively worth about $1billion.

Stars and Stripes

This pair were obviously going for quite the look and went to town when they came up with the stars and stripes theme. Not content with the patriotic nature of their clothes, they have also cleverly added hearts to the patterns to make sure that a romantic feel ran through their senior prom attire. Let’s hope that they do not learn to regret their choice against wearing a tux and ball gown soon, though it must be only a matter of time. Click next to see a famous star’s dress.

Britney Spears

This picture of Britney, looking stunning before going to her prom, is a million miles away from what the singer looks like now. She has been in the spotlight since she released the huge hit, Hit Me Baby One Time and went on to become one of the most successful pop artists of all time. She dated Justin Timberlake for a while – who she met on set of The Mouseketeers. She has children with her now ex husband, Kevin Federline and is currently completing a residence in Las Vegas.

Pretty Pastels

Could this be the most awkward prom picture of all time? There is so much that is wrong with this photo. The boy’s weird nonchalant star, the unnatural hand holding that must have been suggested by the photographer, the girl’s weird tutu come angel dress and the boy wearing a white shirt and jeans. It all adds up to become one very strange coupling. She, however, looks like a very pretty girl and is at the very least trying her best to smile through the awkwardness.

Claire Danes

Claire Danes looks pretty as a picture here in her Prom dress. Who knew this girl would go on to find acting fame through the cult show My So Called Life with Jared Leto and then notoriety for her role in Homeland opposite Damien Lewis. She is now married to Brit actor Hugh Dancy who she met on set of the film Evening. She has also starred in films during her career. One was Leonardo DiCaprio in Romeo and Juliet, in which she was the female lead.

Two Different Proms

You have to ask yourself – are these two going to the same prom together? Whilst the girl may be suffering from a case of too big hair and too much sparkle and frou frou going on with her outfit, she does at least seem to be taking the dress code for the senior prom seriously. Kermit on the right however, has gone exceedingly rogue in his Borat style mankini that he has grafittied himself with a spray on penis. Plus, he’s about a foot shorter than his date.

Harry Styles

Harry Styles, as a Brit, would have had a very different prom experience to many Americans out there. In the UK, they tend to simply have end of year dances that are a lot lower key than their American cousins. That being said, he still looks incredibly handsome here all dressed up for the affair. It was taken just before he found fame with One Direction who were formed during a series of The X Factor. Styles was picked out from thousands to join by Simon Cowell.

Two Cat Shakur

This photo could not get any stranger if it tried. The more you look at it, the stranger it becomes. The cat, for starters, is an incredibly odd prop to be holding in a photo that will become a memento of this couple’s senior prom. Then, add to the mix their weird stare. Isn’t prom meant to be a really happy, joyous evening in a youngster’s life? And then, finally, add in the huge Tiger skin on the wall behind them and you have yourself a very odd snap.

Taylor Swift

Taylor Swift found fame from an early age as a country music singer and has now moved into the realm of superstar. She is one of the world’s most fashionable ladies whose style hits often make the best dressed pages in fashion magazines. Sadly, she had not quite got a hit outfit for her prom. Her evident beauty still shines through, but she has far too much fake tan on so looks unnaturally orange in this image. It remains to be seen whether she wrote a song about her date.

Three French Hens

The girls in this picture have obviously put a lot of thought into what they are wearing. Their dresses are typical prom dresses that means that looking the part at their senior dance is important to them. It makes one wonder why they have chosen to pose with hens as a reminder of this evening. The woods in the background would have made for a nice setting for just the three of them – without the winged animals. Click next to see what a Hollywood hunk wears to prom.

Brad Pitt

The world’s most handsome man still looks dashing in this image, despite his attire that has evidently dated, like his date’s who looks like she is going to walk down the aisle in her 1980s style meringue dress. Not long after this image was taken, Pitt would have landed the role that put him on the path to Hollywood leading man in Thelma and Louise. Since then he has made many a successful movie and dated (and married) many of Tinseltown’s very best actresses.

A Quick Lookey

This boy could not have been caught more in the act if he tried. His prom date has evidently worn a dress to show off her slender figure to the best of her ability – including a deep cut neckline to show of her cleavage. This teenager is obviously making the most of his chance to take a beauty to the ball by making sure he has checked out every inch of skin that her revealing dress is showing. To see what another handsome actor wore to his prom, click next.

George Clooney

This girl probably never thought that by being George Clooney’s date to the prom, she would have a story that she could dine out on for the rest of her life. He’s now not only one of Hollywood’s most respected and likeable stars, he’s also incredibly wealthy owing to a deal he made to sell his drinks company, which he co founded with Cindy Crawford’s husband. He recently attended the wedding of Meghan Markle and Prince Harry with his wife, the human rights lawyer, Amal Clooney.


Is this the most inappropriate Dad photo bomb ever? If we assume that the chap in the background, half naked, is indeed this poor girl’s father. Whilst her style may not be to everyone’s taste and perhaps a little dated for a young girl with pretty features, she certainly does not deserve for her moment to be ruined by her dad embarrassing her. Especially without her knowing. See what one of Hollywood’s most beautiful actresses wore to senior prom by clicking next.

Courtney Cox

The pretty star has made quite the fashion statement here in her prom dress. Her beauty shines through however and the star looks great to this day – especially now she has spurned using fillers and other injections to hold back the hands of time. She famously made a name for herself on the silver screen as Monica from Friends – a part she played for 10 years and made her a large fortune. When the final series was made, each of the stars was making a reported $1million an episode.

Neon A Go Go

Let’s hope there was a theme to this couple’s wedding was neon bad taste, because they would have hit the nail on the head if that was the case. Looks aside, on a more practical note, they both, him in particular, must have got exceptionally hot wearing this get up. It looks to be almost totally plastic which is not known for its breathability when turned into clothing. Given that they were probably dancing at some point, they were both inevitably very sweaty at the end of the night.

Ellen Degeneres

Ellen Degeneres made a bold style decision when she chose this head to toe tartan number. Perhaps the funny comedian was making a joke through her clothes when she turned up to her senior prom. Either way, the star is now a firm favourite with TV audiences and YouTube viewers alike. She has her own eponymous talk show now, but started to become famous when she wrote and starred in the show, Ellen in the 90s. Her quick wit and acerbic humour made the show a huge hit.

Flyaway Hairs

At first glance, this image looks awkward owing to the fact that the girl is looking away, with the gentleman looking directly at the camera. It’s a strange set up that is not at all in keeping with the usual shots taking at a prom. But, then, you spy what’s going on with the girl’s hair and it goes from awkward to plan weird. It is simply a terrible look –  though due respect must be given to the stylist that was able to defy gravity with this one.

Kim Kardashian

The famous reality star and wife of Kanye West took Michael Jackson’s nephew to her senior prom as her date. It should have been a sign of things to come for the woman who claims she was born to be famous by filming a show about her life. She now uses that fame to make millions and is building a business empire through brand endorsements, app development and her own clothing lines, amongst other projects. Not bad for a lady who namely became famous for a leaked sex tape.

Blue Lagoon

Another prom outfit made out of sweat inducing material. Plus, the style of both of these are not flattering to either person – not including the very generous cod piece that can just been made out on the young gentleman’s knight uniform. They’re smiling in the picture, but with a material so unforgiving, they both must soon have suffered from uncomfortable chafing. Plus, it is a wonder if either of them were able to visit the restroom that evening. Read on to see what a famous golfer wore to his prom.

Tiger Woods

Who knew that the lady posing in this picture with one of golf’s biggest stars to be, would also be posing with a man who so famously cheated on his wife? Tiger Woods is equally as well known for his skills on the golf course as he is for his philandering ways that saw him exposed as a serial adulterer. His career made him the first sportsman ever to make a billion dollars – half of which he had to give to his now ex wife in their divorce settlement.

The Statue Of Liberty

This young lady needs to be praised on two things. One, the colour of her dress looks great on her. Secondly, the lace material is quite pretty. From that point onwards, there is nothing to recommend this outfit to anyone. It has obviously been inspired by the Statue of Liberty but the theme has been taken too far so that the dress should really be seen at a fancy dress party as opposed to a senior Prom. Click to see what a popular actress wore to her prom.

Jennifer Aniston

The lady who’s hair is almost as famous as she is, has a style here that is probably soon forgotten. Aniston’s Rachel Cut, however, was probably one of the biggest styles to be requested world over at salons since Meg Ryan’s barnet made waves. Her pretty face is clear to be seen here though and her all American girl look is apparent even before she became famous on the set of Friends. Aniston recently separated from her second husband Justin Theroux. She was previously also married to Brad Pitt.

Throwback Thursday

The amusing point behind this picture is that it wouldn’t have been awkward when it was first taken. Haircuts like the ones so perfectly displayed in this 1980s throwback were all the rage with men sporting Brian May perms and ladies looking like a mix between Axl Rose and Jon Bon Jovi. The fashions on display show why the 80s are so often ridiculed in the press and why most women hide pictures of themselves from that decade. See what a Hollywood Pretty Woman wore to her senior prom, next.

Julia Roberts

The Pretty Woman star seems not to have aged one iota since her prom picture was taken. Her wide smile is on show, as ever, much like her slim physique. Roberts has since become one of Hollywood’s biggest names and is hugely popular with audiences. She makes fewer movies now in comparison to the past as she is a mother of two. She is married to their father, Danny Moder who is a cameraman she met on set of a film she was starring in.

Strong Hair

This couple could, arguably, be well dressed (even today) if you look at them from the neck down. The lady in particular has a chic little black dress on, but when you take in her harsh haircut, it jars the overall look. This is all before you take into account the ridiculous bouffant that is on her date’s head. It is a ridiculous cut and style and perhaps should have been left in the wig shop. For eternity. For a well groomed celebrity throwback, click next.

Natalie Portman

The elfin featured beauty first graced our screens when she landed the role in Leon: The Professional when she was barely a teenager. This picture of her at her high school prom shows her inherent sense of style and also the fact that she has barely aged – even with two decades of acting in Hollywood under her belt. In that time she won an Oscar for her role in Black Swan, the film where she met her husband and father of her children. She is also a Harvard alumni.

Tango Warriors

Whilst satin tends to be the predictable material for girls’ dresses at senior prom, it is usually a predictable mistake as well when they use too much fake tan. The two guys in this picture apparently did not get the memo that said, men just have to hire a well fitting tux. They, instead, got some fake tan and applied it far too liberally to the point that they are glowing in what is otherwise quite a darkly lit picture. Not a look to be repeated.

Scarlett Johansson

The ex wife of Ryan Reynolds has been gracing our screens since she was very young. She had a lead role in The Horse Whisperer opposite Robert Redford and has been acting ever since. She is always looking stunning, much like she does here in her prom picture and it’s good to see that even as a young starlet she still partook in such a momentous coming of age landmark. She is now a mother and one of the highest paid actresses in Hollywood.

Her Hips Don’t Lie

Wow. This is a bold look even for a fancy dress party. Just practically speaking, there is a reason that dresses this wide went out of fashion with women – they simply were not easy to move about in. It seems hard to think of a door that this girl could get through without having to walk like a crab. Her date, too, is no better with a zebra print blazer that is as awful as his matching shoes. She has a pretty smile though.

Angelina Jolie

Those famous lips are as recognisable back then as they are now. Jolie appears barely to have aged since this picture of her going to her senior prom, though she has undoubtedly matured in her life. Once the wild child of Hollywood who famously wore a vial of her second husband’s blood around her neck at their wedding, Jolie is now a UN ambassador and mother to six children – three of whom are adopted. Their father, biological or not, is Brad Pitt from whom she separated after two years of marriage.

Background Check

These two seniors look like the perfect couple. So perfect in fact that they have apparently already planned their future together as a mother and father. Or, what is more likely the case, someone did not think about framing the picture of the two subjects well enough to take out, not only the fire hydrant and tree, but the glaringly obvious planned parenthood sign that makes this prom picture farcical. See what one of the most stylish women in Hollywood wore to her prom by clicking next.

Jessica Alba

Jessica Alba often makes it on to the sexiest women lists – and it is easy to see why in images like this at her prom, even before she has been given a Hollywood makeover. She is now a successful actress, mother and entrepreneur who runs the hugely profitable Honest business that sells ecologically produced beauty products. She initially made a name for herself in films like The Fantastic Four and Blue Crush. Her prom date probably couldn’t believe his eyes when he saw those films.

Winnie The Pooh

One of these two must really have a thing for the fictional character of Winnie The Pooh. Cute as he is, with his round tummy and dedication to eating honey, he just should not be printed on any adult clothing. Especially not adult clothing to be worn to senior prom. It’s a shame as the happy couple both look pretty and handsome respectively but their matching ensembles just draw attention away from their otherwise attractive natures. Click next to see what a previous FLOTUS wore to her prom.

Michelle Obama

The former First Lady of the United States looks stereotypically stylish in this picture of her going to her senior prom. Whilst the fashion may have dated, she wears her outfit with a certain panache that helped make her one of the most popular First Ladies that the United States had ever seen. She is married to Barack Obama who was the first black President. They have two girls together. The Obamas succeeded in having two full terms in the White House and were followed by Donald Trump.

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