Gloriously & Awkward Photos of Celebrities at Prom Night

Long before the days of red carpets, Oscars, and awards the rich and famous were just like the rest of us.  Take a look at this gallery of teenage nervousness and awkward poses as we delve into the world of celebrity prom photos. Although they may be rich and famous now, the likes of Taylor Swift, Blake Lively, George Clooney and Brad Pitt all when through the terrible teens.

Rhianna

Even Rihanna had to start somewhere!  The super-stylish Bahamian beauty now has her own line of sexy lingerie but back in the day she still had a few lessons to learn.

To be fair, Rihanna could never look bad in anything, but this look couldn’t be further than the fashion queen she is today.

Don't take off your corsage, there's more:

Natalie Portman

Natalie Portman could never be anything other than stunning, but what is it with this dress?! It’s hard to find anything good to say about this particular style.

In actual fact Portman’s first film had already made her a start when this photo was taken in 1994.  She obviously took a few more years to develop a personal sense of style.

Meghan Markle

She might have seen the future that night as she left for prom with a royal looking tiara. Well, this is Meghan as homecoming queen at her prom at St Francis High School, in Los Angeles. In the picture, she is 17-years-old. Her prom was back in 1998, when tiaras were actually a big thing, but lucky for us we got to see her with a real royal tiara making her a real homecoming queen. We wonder who's the lucky guy who took her out.

Harry Styles

He may well be a heart-throb these days but back at high school it seems like he was just another awkward teen.  Later, though he would develop his style and go on to date (and break the hearts) of many.

Bella Thorne

American actress Bella Thorne may have been a child model but there was obviously no personal stylist involved judging by this photo taken just before her prom.  No one would imagine that this innocent teen would make history through her pot smoking and partying antics on Instagram.

Amy Poehler

Although Amy favors the casual look these days, she is working the glamour in this picture of her prom.  Later she would become one of the best female comedians as well as a talented writer and actress.

Blake Lively

Gossip Girl Blake manages to look amazing even in a pink glittery prom dress.  Whatever you say about the dress, she manages to totally own this look.

Gigi Hadid

If you use social media you just can’t miss Gigi, she is everywhere!  This stunning supermodel shows that she has that natural style.  Gigi Hadid’s dress is actually pretty cool compared to some of the celebrities on this list.  And she rocks  it.

Lady Gaga

This brunette beauty in indeed Lady Gaga.  It is hard to imagine that this innocent looking Prom Princess would go on to rock out in barely-there costumes and impossibly high heels.

Meryl Streep

Before she was probably the most acclaimed actress of her generation, Meryl was just another all-American teen on her way to her prom.  Later she would receive over 20 Oscars and 10 Golden Globes.

Michelle Obama

After this photo Michelle Obama would go on to graduate from Princeton and Harvard Law School – and later become the First Lady of the United States of America.  She is looking sassy in her pink silk prom dress and she knows it too.

Brad Pitt

You can see the future sex-symbol in the Prom pic of Brad Pitt.  Just a normal guy heading off to a prom with his date.  Way back before his blockbuster movies, Jen or Angelina, Brad had that star quality.

Britney Spears

Britney Spears was already well known by the time she graduated having been a star of the Mickey Mouse Club alongside other notable names like Ryan Gosling and Justin Timberlake.  She is wowing the camera in her prom dress.

Robin Wright

Robin Wright would later become an actress and director and she certainly had personal style at an early age.  Living up to her Princess Bride reputation, she shows red carpet looks all topped with a little tiara.

Lindsay Lohan

Lindsey is pretty well know for being a party animal and living wild.  It is hard to imagine that this cute teen on her way to Prom would party so hard.  Look closer, and there is a glimpse of mischief to be seen.

Ashton Kutcher

Looking smooth, Ashton takes to the dance floor at his high school prom.  Judging from the picture he already has  a small fan club in the making.  Doubtless he was already a heart breaker.

Bruno Mars

The guy who got his nickname for being so cute (he was out of this world according to the girls!) is certainly living up to his reputation in this picture.  He certainly looks as cute as they come in this pose with his former girlfriend from their prom.

Carrie Underwood

Before she became a famous country star with a great sense of personal style, Carrie was a gauche teen just like the rest of us.  Here she is looking very sweet and innocent with her date on Prom night

Claire Danes

Although we can’t really comment on her outfit, Clare Danes looks amazing in this head and shoulders prom pic.  The simplicity of her hair style and make up allows her natural beauty to shine through.  Once she graduated from high school Clare would go on the wine multiple awards as an Actress.

Courteney Cox

A lovely innocent picture of Courtney Cox before she shot to fame as Monica in Friends.  Who would have guessed the future for this bright-eyed teen?

Danielle Fishel and Lance Bass

Not everyone loves their Prom.  ‘N Synch front man Lance Bass took his girlfriend, actress Danielle Fishel to his High School Prom.  Although they looked great, the Prom was so bad they only stayed 20 minutes.

Debra Messing

This picture really is ‘of its time’ - big hair, and silk Prom dresses were all the rage.  Later Debra would prove more stylish and reveal her talent in the hit TV show Will and Grace.

Demi Lovato

Demi Lovato has had a really hard time of late but we are sure she will bounce back.  Take a look back at a happier Demi on her way for a great night out at her prom.  She gives us a peep at future Demi as she flashes some thing in this sassy dress.

Ellen DeGeneres

Ellen started in sitcoms but is now better know for hosting her own TV show.  Ellen stood up and was counted for the LGBT community in Hollywood long before it was mainstream. We all totally love Ellen.

This picture of Ellen  in her prom dress is one of the few you will see of her not wearing her trademark pants and shirts style that she is now famous for.

Faith Hill

This country music queen has sold over 40 million albums and is one of the top country singers of all time.  Faith shows her country roots go way back with this country prom frock, complete with a huge floral bouquet.

Fergie

The super glam Black Eyed Peas front woman always had an eye for a good outfit.  Even when the dress might not be the best she still rocks out.

Fergie has now gone solo but for us she will always stand out as the power pack singer in the  Black Eyed Peas.

George Clooney

Even in high school George Clooney already had those drop dead looks.  All dressed up for a night to remember, his date certainly looks pleased with her catch for the evening.

Halle Berry

Before she shot to fame in that iconic scene in James Bond, Halle Berry was just a cute high school teen in an old-style prom dress.

Only a few years later Halle would be working with Eddie Murphy – Boomerang was a real break through for her and life’s just got better for her ever since.

Jennifer Aniston

Jennifer Aniston is one of those women who just seem to grow into themselves.  Back in the day Jen rocked the brunette locks but now we can’t imagine her anything other than the blond queen of romcom.  Not to mention the fact that she bagged Brad Pitt long before Angelina came along.

Jaden Smith

When Will Smith’s son Jaden went to prom he was not only the coolest kid on the block he also caused a media storm but wearing a skirt.  We think he kills this look and his date looks pretty cute too.

Jennifer Nettles

Jennifer Nettles shows her country credentials with plenty of spangles and huge shoulder pads.  She certainly looks really happy with her look in this striking blue dress.  Jennifer later went on to front the country band Sugarland.

Jessica Alba

It’s a flowery look for Jessica Alba, on her dress and in her hair, all topped off with a corsage. Jessica looks every bit the all-American girl in this picture, and her date looks like he knows he has really lucked out.  What a super cute couple they made.

Jon Hamm

You can see a little bit of the prom night nerves in this photo of John Hamm.

Of course, after this picture, he would spend some time in Los Angeles working towards his big break.  Now this Golden Globe winner is well known for his role in Mad Men.

Kim Kardashian and T.J. Jackson

Looking at this no one would have imagined that this innocent looking prom princess would go on the achieve so much fame and even try to ‘break the internet’!  Her prom date was Michael Jackson’s nephew Tito who was her boyfriend at the time.

Kobe Bryant and Brandy

Even celebrities were just normal teens and Kobe and Brandy were no exception.  Of course, for these 2 teens there were cameras and the media to contend with alongside all the usual prom night nerves but as Brandy said, ‘it felt normal’ and that is a really important part of keeping it real.

Lizzy Caplan

Even before she played Goth girl Janis Ian in the movie Mean Girls, Lizzy Caplan showed her quirky side in this photo taken at her prom.  She event managed to match her hair and nail color.

Lizzy clearly is not taking life too seriously in this picture and she is rocking her look.

Matthew McConaughey

Looking clean and fresh faced Matthew McConaughey really looks the part for his prom picture.  He even managed to coordinate his bow tie with the color of his date’s dress.

As we all know this clean cut young man would go on the star in the movie Dazed and Confused as well as being a producer, actor, writer and director.  A talented young man indeed!

Reese Witherspoon

Even back in high school Reese was showing some serious movie star looks.  Later she would go on to star in the  hit movie Legally Blonde and you can certainly see her star potential in this photo taken at her prom.

Sandra Bullock

Perpetually single star Sandra loves the solo life but back in the day she was clearly have a great time and was very much in love with the lucky gentlemen featured here in the picture taken at her prom.

What a wonderfully, happy picture they make!

Taylor Swift

Always one to make a statement Taylor and her date both chose to wear white to the prom.  At least their outfits weren’t going to clash!

The look like they are having a fun time.  Even though her date’s hat looks slightly ridiculous.

Will Ferrell

It seems that Will Ferrell may have already donned the funny man crown at his prom. You can see the naughty glint in his eyes way back then so no surprise that he went on to be one of Hollywood’s great funny men.

Laurie Hernandez

Laura took the night off from training to enjoy some glamor at her prom.  Ditching the leotard in favor of this long flowing dress, she looks amazing alongside her date.  Laura has been friends with Randall Anderson ever since they first started school together – who better to go to prom with?!

Jeremy Renner

Many years before he played the super-cool Hawkeye  in the Avengers, Jeremy Renner was just another teen on this way to prom.

He looks pretty cute in his tux, all kitted out to match his date’s dress.  We aren’t too sure about the hair though – glad he went on to ditch the mullet.

Presley Gerber

Preseley Gerber has obviously inherited his mother’s good looks – when your mom is Cindy Crawford you have petty much lucked out.  Preseley uploaded this picture saying his mom had made him change his socks – well a guy must look his best. 

Jimmy Fallon

Jimmy Fallon uploaded this picture of his Prom to Twitter. The Tonight Show host was apparently really surprised to see his date so tanned and sporting pretty high heals.  The result was as you see here – a very pale (and quite short) Fallon and probably the most mis-matched prom pairing in history.

Harley Quinn Smith and Lily-Rose Depp

As well as dating for a while Harley and Lily-Rose also went to Prom together and what a stunning pair they are.

Although they both have a mischievous look about them other prom-goers confirmed that they were on their very best behavior.

Gwen Stefani

A lovely picture of Gwen Stefani in a hand made prom dress modeled on Grace Kelly’s dress in the Hitchcock movie Rear Window.

Gwen worked on the dress with her mother and we think she looks amazing.

Paris Jackson

Paris Jackson shows how to do color coordination by dying her hair teal to match her date’s dress.  She doesn’t forget her outfit either – making sure to wear a matching tie. She is totally rocking her look in this picture.

Candace Cameron Bure and Scott Weinger

These two are just too sweet!  Candace Cameron Bure’s date to her real life prom was her Full House sweetheart Scott Weinger.  Sometimes art really does mirror life.

Ariel Winter

Ariel’s look for prom would not look out of place on the red carpet.  From her stunning red locks, to the lacy black and white dress, with its strapless bodice and mermaid train, Ariel rocked out before heading to UCLA.

RuPaul

Back in 1983 RuPaul was already showing his unique and eclectic sense of style.  His prom photo is a clear sign that he has always been a trendsetter.  I think you will agree – he does look pretty amazing.

Bethenny Frankel

This dress sums of the 1980s look – the color, the puffy sleeves and the big hair.  She was at the fashion forefront of the decade.

Later, of course, Bethenny would achieve fame by starring in Real Housewives of New York.

Dinah Jane

Dinah Jane looks perfect in her bright red gown which has all the ruffles any girl could need.  We all stress out about what to wear at special occasions and Dinah was no exception.  Luckily she had Bobby Wesley, the stylist from Fifth Harmony to save the day!

Barack Obama

This is a 17-year old Barack Obama having a great time hanging out with friends back in the day.  Barack wore a dashing white tux which we are sure you will agree was a look he owned.

The former US President’s photo was shared by a former classmate, Kelli Allman, who said that it was a really fun time

Tupac Shakur

Shakur was considered one of the best rappers of all time.  Tragically, he died in 1996 aged just 25 years old.  The rapper wore this fancy white suit to his prom.  His date was the stepdaughter of his friend, KATO.  We think he looks pretty cool in this pic.

Snoop Dogg

Snoop Dogg’s date looks happy but this is a pretty awkward image.  Snoop looks miserable and like he would rather be anywhere else but at his prom. He’s not owning his look either, probably a night (and a photo) he would rather forget.

Tiger Woods

Before golfing fame Tiger Woods was just your average American teen on his way to the prom.

These two look so cute with their matching floral accessories.  Sadly Tiger’s golfing career would later be rocked by scandals, a far cry from these innocent times.

Dakota Fanning

Dakota Fanning ditched the guys and took to the Prom with a group of her chick pals.  She looks every inch a rock chick in her 1990s style pink chiffon prom dress.  Go girls!

Nicole Polizzi

The changing faces of Snooki – from party animal in Jersey Shore to normal, everyday mom, this throwback pic shows her being just an average teen girl enjoying her prom.

She shared the image and told the world how much she loved the night, her date was awesome and she also bagged a bargain dress.  We think she looks fantastic.

Tyra Banks

Tyra Banks is the power behind the Next Top Model series and is a model in her own right.  In fact, she was a ground breaker for black women on the catwalk.  In this picture, taken at her prom, she already has the supermodel looks and stage presence she is now so well known for.

Nick Cannon

It was a while silk suit for Nick Canon’s prom night.  Here is is pictured striking a pose at the bottom of the stairs as he waits for his date. This 17 year old Nick already had a flair from drama.

Ryan Seacrest

Proof that we all have our awkward years – modern day Ryan Seacrest is a world of confidence away from this nervous teen.

He looks pretty cool though and his date is as cute as a button.  What a lovely picture.

Usher

Usher seems to have always had an innate sense of style.  The subtle coordination of his suit with his date’s dress, just a simple rose, speaks volumes about how seriously he takes his style.

Scarlett Johansson

Scarlett Johansson is one of Hollywood’s top stars. This picture of the actress at her prom shows her owning the suit look.  Later she would star in top movies including the Marvel franchise.

Beyoncé