Mariah Carey – Jessica Rabbit
Let’s talk about Mariah Carey pulling out all the stops in 2023 by channeling Jessica Rabbit for Halloween—and no one was ready for this. The queen of Christmas took a break from holiday prep to slay Halloween, sporting a red dress, dramatic curves, and that iconic flowing hair.
Mariah, who shot to fame with her five-octave range and chart-topping hits like "Hero" and "We Belong Together," brought her signature diva energy to the character. This wasn’t just any costume—it was a full transformation with fans buzzing all over social media. Only Mariah could make Jessica Rabbit look even more glamorous. Someone give this woman another holiday, stat!
Rihanna – Raphael the Ninja Turtle
Rihanna took Halloween by storm in 2014, suiting up as Raphael from the Teenage Mutant Ninja Turtles and proving that even a ninja can be fashion-forward. She rocked Raphael’s iconic red eye mask and green armor, looking fierce alongside her girlfriends, each dressed as a different turtle.
Rihanna, who rose to fame with chart-topping hits like "Umbrella" and "Diamonds," has since expanded her empire into fashion and beauty, with her Fenty lines taking the industry by storm. Whether she’s dropping an album or dropping jaws with her Halloween looks, she always knows how to make an impression. Let's face it—Rihanna made saving the world look fabulous that night.
Machine Gun Kelly and Megan Fox – Death Note Characters
Machine Gun Kelly and Megan Fox took their love for anime to the next level in 2023, dressing as iconic "Death Note" characters for Halloween. Megan brought the heat as Light Yagami, rocking a preppy miniskirt, red tie, white stockings, bold red lipstick and space buns to match her fiery hair.
Meanwhile, MGK went all out as the demonic Ryuk, complete with eerie makeup and a dark, devilish look. Megan, known for her blockbuster roles in "Transformers" and "Jennifer’s Body," is a style icon, while MGK’s blend of rap and rock has made him a music sensation. Their Halloween costume might just be scarier than their combined star power.
Khloé Kardashian – Cruella
Khloe Kardashian brought the ultimate Disney villain vibes to Halloween in 2019, dressing as Cruella De Vil and posing with a crew of six real Dalmatian dogs. The star of the show, though, was her daughter, True, who adorably matched her mom as a tiny Dalmatian puppy, stealing hearts left and right.
Khloe, known for her role on "Keeping Up with the Kardashians" and her Good American clothing line, gave the iconic look a glamorous twist with a dramatic fur coat, bold lips, and that unmistakable black-and-white hair. Villainous or not, Khloe’s Cruella look proved that she can pull off fabulous—even with a pack of pups in tow!
Demi Lovato – Snow White
Demi Lovato gave a fairytale twist to Halloween 2023, arriving as Snow White to Vas Morgan and Michael Braun’s star-studded Halloween bash. With a classic blue-and-yellow dress, red headband, and cape, she embodied the Disney princess perfectly—though, knowing her rockstar edge, this Snow White probably didn’t wait for Prince Charming.
Demi, who first rose to fame through Disney Channel’s "Camp Rock" and has since built a successful music career with hits like "Heart Attack" and "Sorry Not Sorry," charms fans for her vulnerability in discussing mental health. Safe to say, no one else rocked a poisoned apple quite like this pop icon.
Billie Eilish – A Cowgirl
Halloween at the Chateau Marmont got wilder in 2023 when Billie Eilish showed up as a stylish cowgirl to Kendall Jenner’s star-studded party. In true Billie fashion, she mixed Western vibes with her signature edgy style—think cowboy hat that matched her pants and boots that screamed anything but basic.
Billie, who skyrocketed to fame with her hauntingly cool sound in hits like "Bad Guy," has continued to push boundaries in music and fashion. Her ability to reinvent herself is what keeps fans hooked. Leave it to Billie to make a cowgirl costume look effortlessly cool—she’s got more than just the Wild West in her lasso.
Justin and Hailey Bieber – Bamm-Bamm and Pebbles
Dressing up as Bamm-Bamm and Pebbles from "The Flintstones," Justin and Hailey Bieber rocked a prehistoric vibe for Halloween 2023 that had everyone smiling. Justin, sporting Bamm-Bamm’s bone-clad look and a club, kept it playful, while Hailey nailed Pebbles' bright green outfit and signature ponytail.
Justin, who rose to global fame as a teen with hits like "Baby," is still making waves in the music scene. Hailey, a supermodel and founder of the skincare brand Rhode, has been making her mark in the beauty industry with her products. Together, they proved that they’re the ultimate power couple, even in Bedrock.
Travis Barker and Kourtney Kardashian – Beetlejuice and Lydia
Travis Barker and Kourtney Kardashian brought all the gothic vibes for Halloween 2023, dressing up as Beetlejuice and Lydia from the iconic Tim Burton film. Travis nailed Beetlejuice’s wine suit and wild hair, while Kourtney, rocking Lydia’s red wedding dress, looked eerily perfect.
Travis, famous for being the drummer of Blink-182, has had a big year with his reunion tour and the release of new music. Kourtney, a reality TV queen known for "Keeping Up with the Kardashians," has been making headlines with her wellness brand "Lemme." Their darkly comedic costume had everyone talking—because let’s face it, who wouldn’t want to crash this spooky wedding?
Heidi Klum – Six Heidi Klum Clones
At her 17th Annual Costume Party in New York in 2016, Heidi Klum took the idea of “being yourself” to a whole new level—literally. She didn’t just show up as Heidi; she arrived with five doppelgängers, each one a perfect clone.
Thanks to some serious prosthetics, makeup magic, and attention to detail, the six "Heidis" walked the red carpet together, creating a surreal spectacle. Known for her iconic Halloween transformations and as the host of "America's Got Talent" and "Project Runway," Heidi has long been a master of taking costumes to the extreme. Who needs one Heidi when six can steal the show?
Kim Kardashian and Kanye West – Catwoman and Batman
In 2012, Gotham got a high-fashion makeover when Kim Kardashian and Kanye West transformed into Catwoman and Batman for Halloween. Kim’s sleek latex suit and mask brought fierce Catwoman vibes, while Kanye’s Batman ensemble added a brooding touch to the duo’s dynamic.
Kim, who became a pop culture sensation through "Keeping Up with the Kardashians," was already making waves with her beauty and fashion ventures. Kanye, a music visionary known for hits like "Stronger" and his Yeezy fashion line, perfectly balanced his dark knight look with style. Together, they turned Gotham’s finest into the most stylish couple of the night, proving even superheroes need a little glam.
Zoë Kravitz and Channing Tatum – Rosemary and Her Baby
Zoë Kravitz and Channing Tatum took spooky couple goals to the next level in 2023 by dressing up as Rosemary and her baby for Halloween. Zoë rocked a vintage nightgown with that signature short blonde wig, giving full Mia Farrow vibes, while Channing wore a onesie, playing the role of her creepy offspring.
Zoë, known for her roles in "The Batman" and "Big Little Lies," has been in the spotlight for her edgy fashion and versatile acting. Channing, the "Magic Mike" star, added his humor to the unsettling duo. Together, they brought some serious 1960s horror vibes to the party.
Ashley Graham and Justin Ervin – Jessica Rabbit and Randy Savage
In 2019, Ashley Graham and Justin Ervin brought some serious star power to Halloween as Jessica Rabbit and Randy Savage. Pregnant and glowing, Ashley slipped into a snug red latex dress, complete with red hair and purple gloves, fully embodying the sultry animated character.
Meanwhile, Justin flexed his muscles as the legendary wrestler, Randy Savage, adding a playful contrast to her glamorous look. Ashley, a trailblazing plus-size model and advocate for body positivity, has been stunning on runways for big designers like Vogue and has embraced motherhood with her three sons as of 2024. Together, the couple nailed the perfect mix of playful and fierce—just like their relationship.
Kendall Jenner – Marilyn Monroe
Kendall Jenner, who became a household name through her family’s reality show "Keeping Up with the Kardashians," has carved out her space in the fashion world, dominating runways and campaigns for luxury brands.
In a stunning nod to old Hollywood, Kendall embraced her inner icon by transforming into Marilyn Monroe for Halloween 2023. Draped in a black sheer bodysuit, she reimagined Monroe’s timeless allure with a bold, modern twist. Her daring Halloween look channeled Monroe’s elegance and reminded everyone why Kendall’s sense of style keeps her at the top of the fashion game. Who knew Hollywood glam could look this daring?
The Weeknd – The Nutty Professor
Halloween 2020 got a hilarious twist when The Weeknd transformed into Sherman Klump from "The Nutty Professor," the character made famous by Eddie Murphy in the 1996 comedy. Complete with a full prosthetic suit, thick glasses, and a plaid suit, The Weeknd fully embodied the lovable professor, turning heads at every corner.
By 2020, The Weeknd, known for hits like "Blinding Lights" and "Starboy," was not only topping the music charts but also preparing for his Super Bowl halftime show in 2021, which he dominated! It’s safe to say, no one else could make a klutzy scientist look this cool.
Jessica Biel and Justin Timberlake – Trolls
In 2016, Jessica Biel and Justin Timberlake turned family Halloween goals up a notch by dressing as characters from "Trolls", with Jessica as the bubbly Poppy and Justin, along with their son Silas, as the ever-serious Branch. The costumes were a perfect fit, especially since Justin contributed to the "Trolls" soundtrack with the infectious hit “Can’t Stop the Feeling!”
Jessica, known for her roles in "7th Heaven" and "The Sinner", added a playful twist to her look with pink hair and a big smile, while Justin, a former "NSYNC" star turned solo artist, embraced his inner grumpy troll. When it comes to costumes, this family knows how to "troll" everyone!
Taylor Lautner and Taylor Lautner – Pete Davidson and Timothee Chalamet's SNL skit
Taylor Lautner and his wife Taylor Lautner (yes, they're both named Taylor) gave everyone a Halloween moment to remember at Heidi Klum's annual party in 2023. They dressed up as Pete Davidson and Timothée Chalamet from their iconic SNL rap battle skit. The couple nailed the look, with Taylor sporting Pete's pink hair and messy vibe while his wife pulled off Timothée's chaotic blue hair and artsy swagger.
Taylor, best known for his role as Jacob Black in "Twilight," has embraced his lighthearted side in recent years, and this costume just proves it. The couple’s costumes brought major laughs and reminded fans of their playful dynamic.
Rachel Zegler – Daphne from Scooby-Doo
Rachel Zegler channeled her inner mystery-solver by dressing up as Daphne from "Scooby-Doo" for Halloween 2023, and it was a total vibe. The purple dress, green scarf, and classic orange hair had fans doing a double-take. Rachel, who rose to fame with her breakout role in "West Side Story" in 2021, brought the same charm and confidence to this costume as she does to her roles.
In 2023, she starred as Lucy Gray Baird in "The Hunger Games: The Ballad of Songbirds and Snakes," showing off her acting chops. But this Halloween, it was all about fun, and Daphne never looked so cool. Looks like Velma’s got some competition!
Ciara and Russel Wilson – Beyonce and Jay-Z
Ciara and Russell Wilson brought major star power to Halloween 2019, dressing up as Beyoncé and Jay-Z from their iconic "Apesh"t" music video. The couple perfectly recreated the looks, with Ciara in a vibrant suit and Russell in a pastel tuxedo, and posed in front of a portrait of the Obamas instead of the Mona Lisa—because why not take it up a notch?
Ciara, known for hits like "Level Up," teamed up with Russell, the NFL quarterback, to deliver a Halloween moment that had everyone buzzing. Their tribute to the Carters was spot-on, and the Obamas have never looked more legendary in a Halloween pic!
Gigi Hadid – The Mask
Gigi Hadid one of the world’s top supermodels, rose to fame walking for brands like Chanel and Versace, and by 2019 she was a household name, continuing to dominate runways and headlines. She brought serious cartoon energy to Kendall Jenner’s 2019 Halloween party in New York City by dressing up as The Mask, and she didn’t miss a single detail.
Sporting the iconic bright yellow zoot suit, complete with oversized polka dots, she also added her own twist—hooped earrings and a glam green face that felt like the perfect modern update. Her take on The Mask proved that even when in costume, Gigi knows how to steal the show.
Dwayne “The Rock” Johnson – Popeye
In 2015, Dwayne “The Rock” Johnson flexed his way into Halloween as a larger-than-life Popeye, complete with the iconic pipe and sailor hat. Of course, it was his massive muscles that took the costume to another level—Popeye never looked so jacked.
The former wrestler turned Hollywood megastar, famous for roles in "Fast & Furious" and "Jumanji", knows how to bring charisma both on-screen and off. By 2015, Dwayne was already cementing his spot as one of the biggest action heroes in Hollywood. His Popeye costume was a playful nod to his brawn, proving that whether he’s saving the world or just eating spinach, The Rock makes everything look epic.
Joe Jonas and Sophie Turner – Gomez and Morticia Addams
In 2019, Halloween got a dose of dark glamour when Joe Jonas and Sophie Turner transformed into Gomez and Morticia Addams. Joe embraced Gomez’s suave style with a pinstriped suit, slicked-back hair, and the famous disembodied hand, Thing, casually perched on his shoulder.
Sophie, channeling Morticia’s signature elegance, stunned in a flowing black gown while artfully trimming a bouquet of roses. Although they are divorced as of 2024, Joe, known for his music career with the Jonas Brothers, and Sophie, beloved for her role as Sansa Stark in "Game of Thrones," showed off their quirky side with this iconic couple’s look.
Lupita Nyong’o – Dionne from Clueless
Lupita Nyong’o brought all the '90s nostalgia to Heidi Klum’s 2018 Halloween bash, dressing as Dionne from "Clueless", and the result was totally "phat." Sporting the iconic plaid outfit, knee-high socks, black heels, and that unmistakable wide-brimmed hat, Lupita nailed every detail of the chic and sassy character.
The Oscar-winning actress, who gained international fame with her powerful performance in "12 Years a Slave", added her own spin to the beloved role, showing she’s a powerhouse on-screen and also at a costume party. With her continuous involvement in big projects like "Black Panther", Lupita proves she can slay both Hollywood and Halloween with effortless flair.
Chrissy Teigen and John Legend – Prince Phillip and Queen Elizabeth II
In 2018, Chrissy Teigen and John Legend gave Halloween the royal treatment, transforming into Queen Elizabeth II and Prince Philip. Chrissy nailed the Queen's look with a perfectly tailored blue coat dress, matching hat, black gloves, and a handbag, not to mention the signature white curls.
John, looking dapper in a red military uniform with a gray wig, played the ever-loyal Prince Philip. Chrissy, known for her candid personality and as a best-selling cookbook author, paired perfectly with John, the Grammy-winning singer-songwriter behind hits like "All of Me." Together, they brought a playful touch to their regal costumes—because let’s face it, when it comes to Halloween, they reign supreme!
Katy Perry – Flaming Hot Cheeto
Who knew a snack could steal the spotlight? In 2014, Katy Perry strutted into Halloween dressed as none other than a giant Flamin' Hot Cheeto, turning heads and bringing the heat. Complete with a bag of Cheetos as her purse, she embraced the costume with her trademark playful energy.
Katy, who rose to fame with chart-topping hits like “Teenage Dream” and “California Girls,” has always had a flair for the unexpected, both on stage and off. Fast forward to 2023, and she’s still a pop culture icon, juggling her music career and a spot on "American Idol". Leave it to Katy to make snack food fashionable and unforgettable!
Black-ish Cast – Black Panther Characters
In 2018, the cast of "Black-ish" turned their Halloween episode into a Wakandan tribute, with Tracee Ellis Ross, Anthony Anderson, and Marcus Scribner stepping into the roles of iconic "Black Panther" characters. Tracee transformed into a fierce Dora Milaje warrior, complete with armor and attitude.
Anthony embraced T’Challa’s royal swagger, while Marcus nailed Killmonger’s rebellious edge. Known for her role as Rainbow on the hit show, Tracee continued to shine that year with the success of her haircare line, Pattern Beauty. Anthony, always a comedic powerhouse, and Marcus, a young star on the rise, made this superhero trio unforgettable. Let’s just say Wakanda looked alive on set that day!
Kevin Hart and Eniko Parrish – 1970's Disco Outfit
Kevin Hart and Eniko Parrish went full disco mode for Halloween in 2012, rocking fabulous 1970s attire at Rihanna’s legendary party at Grey Stones Manor in West Hollywood. Kevin, with his signature humor, looked like he stepped straight out of a funk album cover, while Eniko nailed the groovy vibes in her flared pants and bold accessories.
Kevin, who rose to fame through stand-up comedy and blockbuster films like "Ride Along" and "Jumanji," had everyone laughing on and off the dance floor that night. Eniko, a model and fitness enthusiast, perfectly complemented his vintage look. Together, they brought the party, proving that disco never dies when they're involved!
Cher – Cleopatra
In 1988, Cher took Halloween to royal levels, dressing as Cleopatra in a stunningly sheer dress adorned with intricate silver stones tracing every curve. Her look was topped with elaborate silver headpieces, making her feel every bit the Egyptian queen.
Cher, already a pop culture icon by then with hits like “If I Could Turn Back Time” and her legendary Oscar win for "Moonstruck" in 1988, never shied away from bold fashion. As of 2023, and she’s still captivating audiences with new ventures like her gelato brand and her continued music tours. Cleopatra may have ruled Egypt, but Cher rules Halloween—one sparkling costume at a time.
George Clooney, Cindy Crawford, and Rande Gerber – Two Pilots and a Flight Attendant
At the 2018 Casamigos Halloween bash, George Clooney, Cindy Crawford, and Rande Gerber took off in style, dressing as two pilots and a flight attendant for the night. George, forever the suave A-lister known for "Ocean’s Eleven" and his work as a director, played his pilot role with charm, while Cindy, the supermodel icon, rocked a retro flight attendant look.
Rande, co-founder of Casamigos Tequila alongside George, completed the crew with his pilot uniform. By 2018, the trio had already made Casamigos a household name after selling it for a cool billion in 2017. With these costumes, they proved that first class is the only way they roll!
Elvis Presley and Joan Bradshaw – Casual Outfits
Halloween 1957 saw Elvis Presley and Joan Bradshaw keeping things casual yet cool at a Hollywood party. Elvis, already the King of Rock ‘n’ Roll by then, sported a simple mask that still couldn't hide his star power, while Joan, an actress and model, looked chic in a feathered hat paired with a white top.
Elvis had just released "Jailhouse Rock" that year, solidifying his status as a global icon, while Joan was a rising star making waves in the entertainment world. Even in laid-back outfits, this duo managed to steal the spotlight—proof that when you're Elvis, even a mask can't hide your legendary charisma.
Bette Midler and Elton John – Flower and Vampire
At the New York Restoration Project's 2005 masquerade ball, Bette Midler and Elton John turned heads with their fabulously contrasting costumes. Bette, ever the performer, dressed as a vibrant pink-petaled flower, while Elton went dark and devilish as a vampire, complete with a dramatic cape and signature flair.
Bette, known for her iconic roles in "Hocus Pocus" and "Beaches", continues to thrive with her environmental work through the NYRP. Meanwhile, Elton, a music legend with hits like "Rocket Man" and "Tiny Dancer," had just wrapped another iconic tour. With these two legends in one room, their costumes were bound to be as unforgettable as their careers.
Emma Watson – Wonder Woman
In 2018, Emma Watson swapped her Hogwarts robes for a superhero cape, showing up as Wonder Woman for J.K. Rowling's birthday party. Posing next to a fully costumed Yoda, she looked fierce in the iconic red, blue, and gold outfit, embracing the warrior spirit with style.
Known for her role as Hermione Granger in the "Harry Potter" series, Emma has since become a voice for activism and equality. By 2018, she made waves with her work on gender equality as a UN Women Goodwill Ambassador. Whether she's casting spells or fighting for justice, this costume is the perfect reminder that Emma's always ready to save the day—lasso in hand!
Busy Phillips – Regina George’s “Cool Mom”
Halloween 2019 got a dose of “Mean Girls” nostalgia when Busy Phillips dressed as Regina George’s iconic “Cool Mom” from the 2004 hit film. Decked out in a pink velour tracksuit, complete with blonde hair, Busy perfectly channeled Amy Poehler's character, while her daughter nailed the Queen Bee look as Regina George herself.
Busy, known for her roles in "Freaks and Geeks" and "Dawson’s Creek", has since made a splash with her talk show "Busy Tonight" and her candid social media presence. With this duo’s spot-on costumes, they brought the Plastics back in style—because, as the “Cool Mom” might say, "I’m not like a regular mom, I’m a "cool" mom!"
Sophia Kerr and Margot Robbie – The Shining Twins
Halloween 2016 got an eerie twist when Margot Robbie and Sophia Kerr showed up as the terrifying twins from "The Shining". Dressed in matching blue frocks, complete with splatters of fake blood, the duo looked like they’d just stepped out of a haunted corridor.
Margot, who rocketed to fame in "The Wolf of Wall Street" and by 2016 had fans buzzing over her portrayal of Harley Quinn in "Suicide Squad", added her own Hollywood glam to the spooky look. With those haunting stares and perfectly coordinated outfits, the two turned heads—and maybe even caused a few shivers—proving that sometimes, horror and high fashion make a killer combo!
Mindy Kaling – A Mustard Bottle
Who knew mustard could look so good? In 2018, Mindy Kaling spiced things up by dressing as a bright yellow mustard bottle for Halloween, while her daughter Katherine stole hearts as an adorable lion cub. This dynamic duo turned heads with their contrasting but equally charming outfits.
Mindy, the comedic genius behind "The Office" and "The Mindy Project", always knows how to bring a mix of humor and heart to any event. By 2018, she was already celebrated for her unique voice in TV and film, and she continues to shine with her work on "Never Have I Ever". Safe to say, this mustard definitely added flavor to Halloween.
Lebron James – Edward Scissorhands
Halloween 2019 got a serious upgrade when LeBron James stepped out as Edward Scissorhands, proving that even basketball royalty can rock a Tim Burton classic. Dressed in Edward's iconic black leather and wielding those sharp Scissorhands, LeBron nailed the look.
Adding to the eerie vibe, he posed with a woman dressed as Medusa, creating a hauntingly cool duo. LeBron, widely regarded as one of the greatest NBA players of all time, was dominating both on and off the court by 2019, leading the Lakers while also continuing his impactful work with his I PROMISE School. Who knew the King could make Scissorhands look so, well, sharp?
Kerry Washington – Seong Gi-Hun from Squid Game
Kerry Washington took on the survival game challenge in style for Halloween, dressing as Seong Gi-Hun from "Squid Game". Rocking the signature turquoise tracksuit with “456” emblazoned on her chest, Kerry posed with a hilariously terrified expression, channeling the iconic character’s tense moments from the hit Netflix series.
The Emmy-nominated actress, best known for her powerful role as Olivia Pope in "Scandal", nailed the look with her attention to detail, bringing some pop culture edge to the holiday. In 2023, Kerry has been busy with projects like her memoir "Thicker Than Water" and her continued activism work. Who knew she could make life-or-death situations look so fashionable?
Molly Sims – Jeannie from I Dream of Jeannie
Molly Sims turned heads at Halloween 2019 by stepping out as Jeannie from "I Dream of Jeannie", bringing back all the 1960s magic with a modern twist. She rocked the iconic pink and maroon ensemble, complete with a cropped top, billowy skirt, and a matching scarf tied around her blonde hair, styled into Jeannie’s signature high ponytail.
Molly, who first gained fame as a model and actress, notably starring in "Las Vegas", continues to make waves with her lifestyle blog and beauty tips. By 2019, she was juggling her career and motherhood with grace, but on this night, she proved that some Halloween costumes do come out of a bottle.
Mario Lopez – Captain Crunch
What’s better than Captain Crunch showing up for Halloween? Mario Lopez made sure all eyes were on him as he led his kids to a party dressed as the iconic cereal captain in 2019. With his son Dominic channeling Black Panther’s heroic energy and daughter Gia dazzling as a carnival performer, the family was a perfect mix of fun and flair.
Mario, who became a household name on "Saved by the Bell" and later as a host on "Access Hollywood", proved that his costume game is as strong as his career. Who knew Captain Crunch could look this cool off the cereal box?
Kristen Bell – Elsa from Frozen
In 2017, Kristen Bell decided to let it go—literally—by dressing as Elsa from "Frozen" for Halloween. Ironic, considering she’s the voice of Elsa’s sister, Anna, in the wildly popular Disney franchise. What made it even funnier? Kristen chose the costume in playful defiance of her daughters, Lincoln and Delta, who wanted to be Elsa, too.
Known for her roles in "Veronica Mars" and "The Good Place", Kristen is as hilarious off-screen as she is on. In 2023, she’s been busy with her podcast and parenting projects alongside her husband Dax Shepard. It’s safe to say that even when she’s channeling Elsa, she’s always got Anna’s humor.
Cash Warren and Jessica Alba – Maverick and Romy
Cash Warren and Jessica Alba turned heads at the 2015 Casa Tequila Halloween party in Beverly Hills, serving up some serious nostalgia. Cash went full throttle as Maverick from "Top Gun", sporting aviators and a flight suit, while Jessica hilariously channeled Romy from "Romy and Michele's High School Reunion" with her iconic blonde wig and bold 1990s style.
Jessica, known for her roles in "Fantastic Four" and "Sin City", had already transitioned into a successful entrepreneur by 2015, co-founding The Honest Company, which focuses on eco-friendly products. Cash, a producer and businessman, complemented her perfectly. Together, they proved that mixing 1980s and 1990s vibes makes for a top-tier Halloween duo!
Kim Kardashian, her children, and Jonathan Cheban – Tiger King’s Subjects
In 2020, Halloween took a wild turn when Kim Kardashian and her crew brought the "Tiger King" frenzy to life. With Jonathan Cheban perfectly nailing the eccentric Joe Exotic, mullet and all, Kim embraced her inner Carole Baskin, rocking a floral crown and animal-print ensemble.
Her kids completed the look in adorable tiger jumpsuits, adding to the jungle chaos. Known for her reality TV reign and business ventures, Kim had by 2020, been gaining attention for her work in prison reform. This themed group costume was a playful nod to the year’s biggest pop culture obsession—because, in true Kardashian style, they turned heads as the kings (and queens) of Halloween.
Chrissy Teigen and Kate Upton – Pageant Princess and Marilyn Monroe
At Heidi Klum's 2011 Halloween bash, Chrissy Teigen and Kate Upton delivered a costume pairing that mixed sass with classic Hollywood. Chrissy embraced her inner "Toddlers and Tiaras" diva, strutting in a pink pageant dress, tiara, and big blonde hair that screamed competitive cuteness, all with a hilarious twist.
Kate went full Marilyn Monroe—but with a spooky surprise, adding a skeleton arm painted onto her glamorous look. By then, Chrissy was making her mark as a rising model and media personality, while Kate was quickly becoming an icon with her Sports Illustrated covers. Their costumes were a perfect blend of humor and Hollywood glam, stylishly stealing the spotlight.
Jamie Lee Curtis – Pink Power Ranger
Who knew the Pink Power Ranger could look this fierce? In 2000, Jamie Lee Curtis surprised everyone by suiting up as the Lightspeed Rescue Pink Power Ranger for Halloween, taking a playful jab at the beloved 1990s TV show. With matching pink hair, she went all-in on the look, showing off her fun side while still maintaining her Hollywood status.
Known for her iconic roles in horror and comedy, Jamie has been a fixture in entertainment for decades. In 2023, she added an Academy Award to her resume for her role in "Everything Everywhere All at Once." Whether she’s fighting villains or rocking the red carpet, she’s always a winner!
Cindy Crawford and Rande Gerber – Debbie Harry and David Bowie
Cindy Crawford and Rande Gerber turned heads at the 2018 Casamigos Halloween party by channeling Debbie Harry and David Bowie, and it was pure rock ‘n’ roll magic. Rande fully embraced Bowie’s Ziggy Stardust era, rocking the iconic lightning bolt, fiery red wig, and a bold Union Jack coat that screamed glam.
Cindy, ever the supermodel, nailed Debbie Harry’s punk look with a two-tone wig, ripped tights, knee-high boots, and a bright red plastic phone for that ultimate Blondie vibe. Cindy, known for her iconic modeling career, and Rande, co-founder of Casamigos, owned the night with their edgy throwback. Together, they proved that rock legends never go out of style.