Thanks to teams of stylists, expensive wardrobes, and talented glam squads, it’s easy to forget that celebrities are still people, prone to fashion mishaps and beauty faux pas when they don’t have access to all those things. The easiest way to see a celebrity in a normal light? Check out their prom photos! Before expert filtering and photoshop, before makeup artists and hair stylists, before designer duds and tailoring, celebrities didn’t always knock it out of the park when it came to dressing up for a formal event. Five of the celebs on this list definitely fell short when it came to getting glam for prom, while the other 15 showed us all how it’s done!
Even with access to everything we’ve mentioned already, style isn’t something that can be bought, and 15 of these beautiful ladies still managed to ~werk it~ with a prom dress they bought from a mall and makeup they did themselves. Like all things, some succeeded better than others, but every single one of them looked drop dead gorgeous! As for the other five, well, it’s a good thing that there are only a couple photos of their prom dress mishaps since they all happened before everything was on the internet, giving us all an intimate look at their worst looks! Where does your prom look rank among these 20? Which would you wear and which would you never be caught dead in?
20 Blake Lively’s Barbie Bodice
The Internet is a great thing, which is how we were able to scrounge up this photo of actress Blake Lively at her prom! Considering the awe-inspiring styles we’re used to seeing the star in, this prom dress definitely falls short, but that doesn’t mean it wouldn’t be gladly worn by a lot of high school girls to prom even now! Sure, it’s extra-glittery, with a major Barbie feel, but Blake is the kind of woman who – even during her teenage years – could look good in just about anything!
With all that bling and all that pink, we can see why Blake has since chosen such luxe looks when walking down the red carpet in recent memory, proving that her thirst for attention when it comes to fashion has been around since high school! Fortunately for her, though, her hair has definitely gotten better since those uber-straight bangs and tiny tiara, but really, whose strands didn’t fall victim to a straightening iron during the 2000s? While Blake’s formal look certainly isn’t as ageless as the blonde beauty, she still looks like a knockout on her big night, and we can’t fault her for getting her Barbie on the back when such styles were considered totally chic!
19 Gwen Stefani’s Ode To Grace Kelly
Now, this is what we’re talking about for a Throwback Thursday! In honor of Instagram’s weekly #TBT post, singer Gwen Stefani shared this snap on her own account and showed that she had some designer skills before she actually got her own celebrity fashion line.
This photo, taken when Gwen was 17 and headed off to prom in California, shows the singer in a dress she made with her mom. The black and white concoction is classic, which makes sense since it was inspired by actress Grace Kelly’s role in the 1954 film Rear Window. The off-the-shoulder silhouette is certainly flattering and timeless, and we love the bold black and white that stands out from the myriad of jewel tones and pastels that no doubt populated Gwen’s prom. The only thing we’re not quite fans of are the gloves, which, while staying true to Grace Kelly’s character, read a little costumey to us. Other than that, we’re vibing on her look, which is formal enough without going too over the top. Clearly, Gwen was ahead of the curve when it came to style – even as a teen – and so this prom look is a win! Plus, now we know where she honed her fashion skills!
18 Dakota Fanning Looks Pretty In Pink
Bursting into the limelight when she was just a little thing, it still might throw people for a loop when they see actress Dakota Fanning all grown up. One look at her in this pretty pink prom dress, though, and you can see that Dakota looks more mature and beautiful than what we were used to before this photo!
However, if the dress looks familiar, it’s because Dakota went practical and actually recycled it from a previous event! Prior to her 2009 prom, the actress was snapped wearing the same pink taffeta bubble-hemmed dress to the February 2009 premiere of her film Coraline! Considering the amount of designer picks that were at her fingertips, it’s nice to see Dakota opt for re-wearing something she already loved.
Increasing her relatability factor, despite being a famous child star, Dakota also admitted in an interview that in terms of prom prep, she didn’t have a date – not that she was at all bothered by it! “I’m trying to decide if I wanna go with someone or just go with friends. Sometimes it’s easier to just go with friends.” Hey, considering the actress was crowned Homecoming Queen two years in a row and was on the varsity cheerleading squad, we imagine she had her pick of people to bring as her date!
17 Danielle Fishel’s Ice Queen
How’s this for a ‘90s teen dream? Boy Meets World star Danielle Fishel went to her prom with *NSYNC band member Lance Bass (prior to his coming out) and the two epitomized all that the decade had to offer. From her platform sandals and spaghetti straps to his highlighted and spiked hair, we don’t know which part of this prom look is our favorite!
The couple was actually together at the time, and apparently, Lance wasn’t going to be able to take Danielle to her big night due to scheduling conflicts, before he pulled out a big romantic gesture that would do *NSYNC fans proud! The boy band member sent the actress “three dozen roses in the mail with a card that said, ‘Plans have changed. I’ll be in town. Can I take you to prom? Check yes or no.’ And there were two little boxes! So, of course, I checked the box yes.”
While the 1990s had a lot of unfortunate fashion choices, Danielle’s dress for the evening wasn’t one of them. With a saucy slit and back cutout, she managed to bring a little sultry appeal to her look while not totally obscuring her kid-friendly TV persona.
16 Jennifer Aniston’s Basic Black
Let’s ignore the 1980s hairstyle that actress Jennifer Aniston is wearing in this prom photo throwback, and focus more on that dress, which still manages to draw major envy decades later!
We know that Jennifer is a fan of black (seriously, check out some of her many, many LBDS here), but, while this silhouette is pretty simplistic, it is anything but basic. For her junior prom in 1987, a 15-year-old Jennifer knew how to accessorize and work her angles! This sweetheart neckline black dress looks to be made of a heavier material, possibly even velvet, and, with just a simple necklace and some drop earrings, the actress shows how if something ain’t broke, don’t fix it! We love that she chose something classic that stands the test of time – even if that suburban mom haircut doesn’t. The LBD has long been one of the actress’s BFFs, but we can’t say the same for her date. Allegedly a junior named Clemens Wust, who attended Rudolf Steiner School (Jen later switched to prestigious art high school), we have no idea if Wust and Jennifer are still friends. (Sorry, we had to.)
15 Bella Thorne’s Bejeweled Bodice
Nowadays, we’re used to seeing actress Bella Thorne walk around in outfits that make us kind of scratch our heads, with her hair any of the colors of the rainbow, multiple piercings, and heavy makeup. Once upon a time, though, back in 2013, Bella decided to really work with her natural coloring, with a seafoam green mini-dress with tulle skirt and bejeweled bodice. A classic prom choice from designer Sherri Hill, Bella was super cute!
This is just the first of a few prom dresses we’ve seen Bella rock over the years, as her wardrobe choices have gotten more and more daring. The following year, the actress rocked a sequined and embellished black and silver halter-necked gown, again by Sherri Hill, whose line Bella has modeled for on multiple occasions. Then, by 2015, the former Disney Channel star took things up yet another notch, this time with a bodycon white dress that went to the knee and left little to the imagination! Looking at all three dresses side by side, we can certainly see how Bella’s style has evolved with the years, but this green one was too sweet not to share!
14 Shay Mitchell’s Fabulous Fuchsia
Another actress who likely had her pick of dates but chose to hit up prom with her friends, Pretty Little Liars alum Shay Mitchell may have broken a few dress codes when she chose this daring fuchsia gown, but we’re so glad she did! The color is what really makes this dress a winner, since it pops against Shay’s skin tone and lets her keep the rest of her look simple, with natural makeup, unadorned hair, and long earrings. In fact, a year after her 2011 prom, Shay spoke to Seventeen about her choice to let her dress speak for itself, saying, “For my prom, I wanted a really bright color – something that was going to pop and stand out. [You have to think about] how you are going to shine in your photo and how you’re going to look different.” Well, we say mission accomplished!
Paying attention to budget, Shay’s dress just cost $175, and she raided her mom’s closet for accessories. In fact, rather than have a big glam team to help her get gorgeous, it was Mama Mitchell who styled her daughter’s hair! (Twice, actually, since the first time didn’t pan out too well!)
13 Gigi Hadid Is A Lady In Red
When you’re a gorgeous supermodel like Gigi Hadid, it’s almost impossible to look awkward in a photo, even something as stilted as prom. Plus, when you consider her high fashion IQ thanks to years of strutting her stuff down the runway, of course, Gigi’s prom look was going to be a total knockout!
Eschewing the traditional fussy extras like lace, tulle, or glitter, Gigi went with a stunning red sheath dress, with extra detail around the neckline and waist for her 2013 event. While this look totally works for a formal event, it could easily transition into something for daytime or business, rather than rotting away in some forgotten corner of her (admittedly extensive) closet.
It looks like sister Bella took a page out of her big sis’s book when it came to dressing for prom, too, opting for a similar style, with a white, figure-flattering dress that had detail along the chest. If her photos are anything to go by, it looks like Gigi had an amazing night surrounded by her best girlfriends, some photo booth props, and lots of funny faces! Is there any better way to celebrate the end of high school?
12 Robin Wright’s Princess Pose
If you were a fan of The Princess Bride growing up (and really, what childhood was complete without at least one viewing of the classic?), then you can see why actress Robin Wright won the role of Princess Buttercup, because she looks positively royal in this prom photo!
Back in 1981, the actress wore a simple, strapless, dark-colored dress (we’d guess navy blue, but with black and white photos, it’s difficult to tell), which she accessorized with a classic strand of pearls. Perhaps unsurprisingly, considering how radiant she looked, Robin was crowned Homecoming Queen the same year!
We’re in love with how timeless and perfect the House of Cards actress looks in this photo, which came a few years before the 1987 film that would make her famous, and can see how she nabbed the role after seeing her pose like this! While the rest of her gown can’t be seen in this photo (you can get a slightly better look at it here), it’s a classic A-line shape that flatters almost every body type, and showed the actress’s penchant for simple silhouettes that would become her red carpet signature style.
11 Demi Lovato’s Red Ripples
Some celebrities forget their roots once they become famous because they’re so caught up in their glamorous life – but not Demi Lovato! In 2010, the singer and actress made good on a kindergarten promise to friend Nolan Narddechia and flew back to her hometown of Dallas to attend prom with him!
For the big night, Demi opted for a strapless red dress with a sweetheart neckline that looks like it was just meant for twirling. While we’re not in love with the over-tanned look she’s got going on, we do love that she kept her hair looking dark and lush, with just a simple clutch and that prom staple – a corsage – as her major accessories.
While Demi clearly understands that loyalty and promises are big (even when you’re a four-year-old making them), we appreciate that she stepped things up a bit with some old Hollywood glam. Rather than head off to prom in the usual limo or parents’ car, the singer pulled out the big guns and provided a vintage Rolls Royce! Clearly, Nolan Narddechia made the right decision when he tapped a toddler-sized Demi to be his future prom date!
10 Amandla Stenberg’s Casual Cool
We feel bad for anyone who was standing next to or sitting beside Amandla Stenberg and Jaden Smith at the former’s 2015 prom, because, wow, do these two look good! All the bejeweled necklines and tulle skirts in the world couldn’t compete! Both stars aren’t exactly known for playing by the book and tend to get more than a little daring in their style choices, treating fashion more like a playground than simply clothes, and they really pulled out all the stops when they paired up.
It’s all about the dress, though, and Amandla’s bronzed halter-neck number with sheer skirt looked insanely gorgeous on the actress. Complete with a septum piercing and silver-painted braids, Amandla showed that there’s no right way to do prom – although her look was very, very right!
We have to talk about Jaden’s ensemble, also. While some outlets described his look as a “midi-length skirt and tunic combo”, others said the son of Will Smith was straight up wearing a dress, as he’s done many times before. Hey, we have to say that he looks pretty cool, and it’s certainly a step up from his superhero getup, which he wore to another prom that same year!
9 Lottie Moss’s $60 Steal
You might not be familiar with the name Lottie Moss, but the little sister of supermodel veteran Kate Moss clearly knows a thing or two about fashion – and what’s worth shelling out big bucks for!
A model herself and “It girl in the making”, Lottie chose a white off-the-shoulder gown in a figure-hugging silhouette that wouldn’t look out of place on the red carpet or walking down a runway. For her Leaver’s Ball in 2016 (which is the British version of prom), Lottie certainly had her pick of many designer duds, like the dreamy gowns she wore to the Cannes Film Festival by designers like Balmain and Dior, but, instead, the practical high schooler chose a dress that cost a very reasonable $59.50 from British store Missguided.
Rather than have a full glam team in effect, Lottie’s stylist Emmanuel Ezugwu told Teen Vogue, “For her prom dress, she found it herself and didn’t need styling. She wanted to do it by herself like the rest of her mates, which I think was the right thing to do.” Hey, when your prom pick is this stunning, it doesn’t require much work to pull the whole look together!
8 Kylie Jenner’s Nude Hues
Kylie Jenner has had an upbringing that was anything but normal, thanks to being filmed as part of Keeping Up With the Kardashians for over 10 years, but in 2017, the reality star and beauty entrepreneur (and new mom) decided that she wanted a dose of normalcy, and so decided to attend prom. Kylie had been home-schooled throughout her life, and thus was never given the opportunity to attend the big formal dance and so, along with BFF Jordyn Woods, the two headed into prom in Sacramento, California – all of which was shown on her own TV show, Life of Kylie, of course!
After hearing about junior Albert Ochoa’s prom date rejection (he was the brother of his date’s best friend), Kylie and Jordyn stepped in. While Jordyn opted for an empire-waisted red dress, it was Kylie figure-hugging, the one-shoulder nude dress that really stole the show! We know that the reality star is famed for flaunting her figure, and this prom dress, while perhaps not abiding by stricter dress codes, looked stunning on the starlet, who kept the nude theme going with natural makeup, loose locks, and a minimal corsage. Love her or hate her, you can’t deny that the girl looks good!
7 Elle Fanning’s Enchanted Forest
While big sister Dakota managed to make it to her prom and even joined her cheerleading squad and won Homecoming Queen two years in a row, Elle Fanning had career obligations that prevented her from attending her own senior prom – but that doesn’t mean she didn’t dress up for it!
Rather than fly home for a high school dance, her date actually flew out to France where Elle was working at the Cannes Film Festival and recreated the special evening with her – boutonniere and all! Dressed in an ethereal Zuhair Murad confection that featured embroidered flowers on the bodice and down the skirt of the pale pink dress, Elle didn’t spare any expense in her semi-fake prom, even trotting out the Tiffany jewelry! Fortunately, her style smarts prevailed and the actress kept her hair and makeup simple and sleek so as not to compete with the rest of the lavish look. While not held with all her school friends, we think that this look was too gorgeous to leave out, and, since Elle and her date did do prom their own way, we figure it still totally counts! We totally love how innocent and sweet Elle looks in this gown. It just goes to show she's definitely not growing up too fast despite being in Hollywood most of her childhood.
6 Ariel Winter’s Lace Look
Now this is how a celebrity does prom!
For her 2015 prom, actress Ariel Winter chose a navy blue lace dress with a dramatic back cutout and a sheer overlay covering the deep V-neck. The dress fit the actress like a glove, with a figure flattering shape that hugs her curves and an elegant floor-length hem, and the drama continued with her beauty look, featuring long, dark, curled hair and a killer smoky eye.
However, if you’re thinking that this dress looks a tad familiar, you wouldn’t be wrong – Ariel wore an almost identical look for her 2016 prom! That year, the major difference was that her lace dress was strapless with a mermaid silhouette. Coupled with her fire engine red hair, she was giving us serious Little Mermaid vibes in the best way possible! This one gets just a little more edge, though, because of how flattering it is on the curvaceous starlet. Without giving everything away, Ariel looks every inch the bombshell but still totally appropriate for a high school-age event. Clearly, she found a prom formula that works, and we can’t blame her for sticking to it!
5 Taylor Swift’s Ill-Fitting Ivory
Taylor Swift is definitely an icon in the industry today, and she's been praised and criticized for her looks over the year, but unfortunately, her prom look wasn't her best one. We love her beauty look, with her country girl curly blonde hair loosely held back, minimal makeup, and delicate jewelry, but her dress leaves us wishing she’d chosen a different material or taken it to a tailor (no pun intended).
It’s hard to make the ever-stylish musician look anything short of perfect, but the wrinkled ivory gown isn't something most of us would expect her to wear, it just looks like it could use some lining. It seems that even Taylor wanted a do-over when it came to prom when, in 2008, after having to miss her senior prom due to her touring schedule, she went on MTV’s show Once Upon A Prom! Choosing from 50 dateless dudes, at Hillcrest High School in Alabama, Taylor picked Whit White, whom she called “so down-to-earth and all-American…he was unbelievably sweet”. With BFF Abigail taking Whit’s BFF with her, Taylor opted for a strapless pale pink number which still failed to wow, but was definitely fitting for Taylor’s fashion era of the time! Prom without the pressure proved to be a winning formula for the singer, who described the night by saying, “I felt so much like I was in high school again – in a good way, without any drama…It was the coolest thing!”
4 Jessica Alba’s Fussy Florals
Jessica Alba is a lot of things: actress, entrepreneur, mother, and, apparently, a former ice skater, judging by her prom dress pick! This dress was certainly of the times, with the signature late 1990s face-framing strands of hair. Add to that the velvet bodice, tiny floral embellishments, and frothy tulle skirt and you’ve got a lot going on! While Jessica is still undeniably beautiful, the dress doesn’t do her any justice.
In case you were curious, the guy lucky enough to be Jessica’s prom date was her high school boyfriend Chris Lakkees, who didn’t know how good he had it! The couple broke up soon after the prom photo was taken and, in an interview with TMZ, Lakkees was still mourning what could have been – thirteen years after the fact! The couple dated for five years before Jessica ended things, which inspired Lakkees to develop a website called RelationshipCourt.com, which was designed to try and stop unnecessary breakups, although the definition of “unnecessary” here seems a little arbitrary. In the interview, he said that he “always wished that someone would have mediated between Jessica and [me] so that [we] could have at least stayed friends.”
3 Lizzy Caplan’s Not-So-Great Hair Day
Maybe Lizzy Caplan just has a thing for purple, or maybe she’s more like her Mean Girls character Janis Ian than we thought, but either way, we can’t really get behind this out of the ordinary prom look! Kudos to Lizzy for matching her hair to her date’s, via some complicated ties or braiding but, coupled with the cow-print patterned jacket, we think that this photo, while hilarious, is the kind of super awkward thing that follows when you try and get a little TOO original on prom night.
Lizzy isn’t usually the actress that comes to mind when we think of fashion risk-takers and daredevils, but, back on her prom night in 2000, she definitely marched to the beat of her own drum! Leaving aside the not-so-great hairstyle, we’re just not loving the spaghetti-strapped brown-colored dress that looks to be made of some iridescent material. (It may not be brown, but that’s how it appears in this light.) Lizzy is a gorgeous woman, and she has definitely looked ultra-glam on the red carpet since becoming a bonafide star thanks to her recent work but, back then, she just didn’t hit any of the high notes. (Although we have to expect the bravery in leaving the house looking like this!)
2 Ellen DeGeneres’ Plaid Pain
The throwback to end all throwbacks, we have Ellen DeGeneres here looking very 1970s with her plaid dress, feathered hair, and long-haired date with gargantuan bow tie and platform shoes! We kind of love everything that is awkward and high school-age with this photo, including their poses as well as their outfit choices, but even Ellen knew that this dress wasn’t a winner! In an Instagram post, in honor of Throwback Thursday, Ellen simply wrote, “Yes, this is real.” On her show, where she’s regularly shared her own “bad prom photo”, the talk show host even referred to her dress as being made of drapes. Hey, we weren’t gonna say it, but she’s not wrong!
In an adorable turn of events only Ellen could manage, she actually stayed friends with her prom date, Richard, over 40 years later! In fact, on her show in 2005, she and Richard even recreated their infamous prom photo!
It’s great that the talk show host and comedian is able to look back on this photo and laugh because that fashion choice is definitely a prom fail, it almost made our number one spot, but we reserved that for something truly spectacular.
1 Kellie Pickler’s Odd Two-Piece
Okay, a couple prom dresses on this list might have toed the line of dress code rules, depending on how strict the school was, but country singer and American Idol contestant Kellie Pickler threw any and all rules out the window when she showed up to her junior prom in this ab-baring ensemble!
We’re looking at the early 2000s when this photo was taken, and low-rise jeans were all the rage, so why not have a low-rise prom dress? A regular feature on lists of the worst prom dresses ever – celebrity or otherwise – Kellie’s “gown”, with cutouts along her midriff, tube top, a belly button ring all look way out of place at a formal event, even if that formal event is happening for a small town high school. There’s no way this look could have aged well, and, while Kellie looks gorgeous in spite of her questionable fashion decisions, this dress is making history for all the wrong reasons.
Fortunately for us – and posterity – Kellie’s style has grown up a bit and, while she has occasionally enjoyed a good midriff-baring outfit, she’s definitely toned things down, which is easy to do when things are already up to 11!
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