Art & Style

How Far Is Too Far? Hollywood’s Most Bizarre Red Carpet Looks

Can money buy taste? We’ve compiled a list to test that theory with our pick of some of the strangest outfits to parade down the red carpet. Perhaps unsurprisingly, a lot of the most “out there” outfits have featured at annual Met Gala events, where attendees are encouraged to go all out.

Hollywood Out There Looks New Intro Image
Image: Teen Vogue

Whatever the designers and wearers were trying to say with these questionable designs, it’s clear they wanted all eyes on them. We say, hats off for daring to be different! As some of these statement pieces were no easy feat, requiring some serious backbone, figuratively and literally.

Serena as You’ve Never Seen Her

Tennis Legend Serena Williams stepped out nothing short of majestic for this year’s Met Gala. Her neon-yellow Versace gown looks straight out of a fairytale, from the exaggerated, billowy shoulders, to scattered pink leaf embroidery, she certainly took the gold this evening.

Hollywood Out There Looks New 11
Image: Yahoo

We love that she opted to wear highlighter-yellow Nike Air sneakers with this gown instead of “acceptable” and uncomfortable heels, reminding us that we don’t need to suffer for the sake of beauty in 2019. They also served as a nod to her greatest achievement – her sporting legacy. Serena literally radiated at the 2019 Met Gala.

The Denim-Duo of Your Dreams

This moment in pop-history really happened. Britney Spears and Justin Timberlake came through in matching head-to-toe denim outfits, complete with iced jewelry that wouldn’t look entirely out of place in a costume wardrobe. It was 2001, and these pop sensations wanted to establish themselves as some type of power couple…we guess.

Hollywood Out There Looks New 5
Image: Daily Mail

Looking like a special-edition Barbie and Ken, Britney stepped out wearing a denim/prom dress hybrid with a confusing selection of accessories, while Justin sported a full Tuxedo with matching belt and cowboy hat. And the hat had a jean waistband. Once you’ve seen it, it can’t be unseen – or forgotten.

Take a Bow for Pope RiRi

Yes, Rihanna came as the Pope for the 2018 Met Gala. This John Galliano creation took the theme of the year’s Gala, Heavenly Bodies: Fashion and the Catholic Imagination, and ran with it. Vogue editor-in-chief Anna Wintour sang Rihanna’s praises for her bold look, declaring “I can never get enough of Rihanna’s style… I think there’s a real love of fashion with Rihanna, and how lucky are we to be able to enjoy it?”

Hollywood Out There Looks New 7
Image: New York Times

However, not everyone echoed Wintour’s admiration. In reality, it crossed a line for a lot of people, causing offense to much of the Catholic community. Accused of sexualizing the Pope, mocking Christianity and appropriating Catholic culture, the jewel-encrusted show-stopper definitely got people talking about whether A-listers know how far is too far.

Attention-Seeking Angel Katy Perry

Reminiscent of a Victoria Secret runway show-stopper, Katy Perry opted to go as a metallic-brass angel to the 2018 Heavenly Bodies: Fashion and the Catholic Imagination Met Gala. She also appears to have knelt in the middle of the grand staircase in front of the paparazzi, just in case you didn’t see her.

Hollywood Out There Looks New 8
Image: New York Times

Certainly one of the more imposing designs to feature at a Met Gala, Perry seemed eager to pull off a performance, rather than just a look. She also arrived at the event standing tall in a white roofless vintage car, wings akimbo. The Versace minidress and thigh-high boots are simply overlooked next to the towering angel wings.

Janelle Monae Does Not Shy Away

Singer-songwriter Janelle Monae was one of the 2019 Met Gala attendees who opted for a split look, not super practical but eye-catching at least. Featuring a monochromatic look on one side and more flirty, revealing look on the other side, it’s clear to see how Monae connected her outfit to this year’s theme, Camp: Notes on Fashion.

Hollywood Out There Looks New 10
Image; Harpers Bazaar

Designed by Christian Siriano, Monae was a statuesque tribute to the inspiration behind the theme: Susan Sontag’s 1964 essay Notes on “Camp” – credited as having introduced the notion of camp. She states, “its love of the unnatural: of artifice and exaggeration”, drawing connections to its influence in queer culture. Siriano and Monae’s interpretation of the concept is playful and one-of-a-kind.

Peacock in Purple: Hamish Bowles

Vogue editor Hamish Bowles worked with John Galliano to create this ostrich-feather cape monstrosity. To top it all off, it has neon pink poodles stitched among the mohair and lurex threading, adding some humor to the purple chaos. We love this interpretation of the camp theme, culottes and all.

Hollywood Out There Looks New 9
Image: The Wrap

Reliving the moment he first tried on the ensemble, Bowles’ said, “Sure enough, when I put on the cloak and began walking up and down the studio and it caught the air in its massy volumes, it lifted up like a cloud, and, despite the thick feather fronding, seemed almost as light as one.”

When My Little Pony Meets Hip Hop

Remember when Nicki Minaj made a name for herself as the candy-colored rap princess? She’s sported some out-there looks over the years, but we have a soft spot for this particular homage to the ’80s. The cone bra, the cotton-candy hair, the attitude – it’s all very Minaj circa 2011; loud and bizarre.

Hollywood Out There Looks New 6
Image: Bustle

Also part of the ensemble on the night was a colorful surgical mask covering her nose and mouth, reminiscent of Japanese Harajuku fashion. While uncomfortable looking, the metallic dress does make Minaj seem statuesque or doll-like, fashioning her into an object of sorts, inviting people’s gaze.

Whoopie Goldberg Has Never Cared What You Think

Goldberg’s unique dress sense is far from new. She’s known for expressing herself unashamedly, and that certainly extends to her clothing choices. We love this maleficent-style fairytale look she wore to the 1993 Oscars; you don’t see enough lime-green lining these days.

Hollywood Out There Looks New 2
Image: Yahoo

Interestingly, she could choose to wear this as a gown (with the petticoat down) or as a pants suit/cape situation; it’s nothing if not versatile. On her style philosophy, she’s stated: “My suggestion to other people is, ‘Try stuff!’ Maybe it doesn’t work, but maybe it does.” Either way, we’re loving that she doesn’t take herself too seriously.

Cara Delevingne Serves Us Sci-Fi Chic

The ultimate power suit. This heavily bejeweled pantsuit was causing major camera flashback at the 2017 Met Gala. Designed by Chanel, the two-piece was accompanied by a Chanel rocket ship purse and chrome stilettos. In typical Chanel style, they experimented with an unusual outfit concept, but in a classic tailored silhouette.

Hollywood Out There Looks New 13
Image: Glamour

Having completely shaved her head for her role in upcoming teen drama Life in a Year, makeup artist Romy Soleimani incorporated her bold new style in the best possible way. She highlighted her head in a reflective silver pigment, adorning it in jewels and making it a true crown. Delevingne looks straight out of the future and we can’t wait to join her.

Always Get a Second Opinion

The ESPYS in 2015 were hosted in Los Angeles, for which WWE wrestler Ronda Rousey wore a bizarre black and white cut out dress that looked more like a junior school sewing experiment. If anyone has the body for such a cut-away dress it’s Ronda. We just can’t help but feel there was more potential…

How Far Is Too Far Hollywoods Most Bizarre Red Carpet Looks 100
Image: Hollywood Reporter

The contrasting panels are hardly complemented by the fishnet sleeves and matching waist cut out. Neither is the sheer chest and underarm netting. Even the back of the dress is just as confusing, combining an open back design with more polka dot mesh and white paneling, brought together with a large zip. A really unique choice!

Fearless on and off the Court

Of course, Dennis Rodman! Known for his eccentric style, the retired basketball player has had some out-there looks. From bold makeup looks, multicolored hair dying to even a wedding dress, it’s refreshing to see someone, especially a sportsman, divert from what’s expected of them.

Hollywood Out There Looks New 3
Image: Seattle Met

Rodman hasn’t always been so confident, having described himself as withdrawn in his childhood and not feeling comfortable in his body. Clearly, he’s learned to embraced himself since. We like this toned-down, gender non-conforming outfit choice from 2005; he looks great in a crop top and sarong.

When You Can’t Choose Between Two Outfits

Talking of gender non-conforming, Michael Urie went for a bizarre mismatch of two styles. Similarly to Janelle Monae, he chose an ensemble that was split down the middle for the 2019 Met Gala, Camp: Notes on Fashion. However, his interpretation is a little more literal – one side is a fluffy pink ballgown, the other a pinstripe tuxedo.

Hollywood Out There Looks New 16
Image: Refinery 29

It probably won’t surprise you to learn that the person responsible for this, Christian Siriano, is the designer from Janelle Monae’s split creation, too. Commenting on his design earlier this year, Siriano stated on Instagram that “you can be your own prom date no matter who you are!” A noble sentiment.

They Say Bright Lights Attract the Eye

Maybe she felt she a bit unnoticed the year before as a giant-winged angel, which is why she opted to come to this year’s Met Gala as a working chandelier. This Moschino design was one for the books, using two built-in battery packs to power up the dress, and Swarovski crystals for extra reflection on the corseted dress itself.

Hollywood Out There Looks New 14
Image: HuffPost

This three-tiered look tapers to the literal “point” of the get-up – the light fixture balanced on the top of her head. For us, the word ostentatious comes to mind, but I guess that’s to be expected from the pop singer after witnessing her kneel in prayer at the steps of last year’s Met Gala.

Sarah Jessica Parker Reigns Over the Gala

Like Rihanna, Sarah Jessica Parker also opted for a monarchical religious-style for 2018’s Met Gala, Heavenly Bodies: Fashion and the Catholic Imagination. A vision of gold and red, her exaggerated sleeves, draping train and hefty headdress really did distinguish her as Met Gala royalty.

Hollywood Out There Looks New 12
Image: Vogue

Brought to life by Dolce & Gabbana, they even created a nativity scene inside the headpiece itself as a homage to the theme of the gala. The attention to detail is outstanding, as can be expected as they often incorporate religious themes into their designs. This outfit is what happens when you let your imagination run wild.

Jared Leto Takes Himself to the Met Gala

The saying “head in hands” rarely conjures up an image as literal as this. Surely one of the most attention-grabbing looks of all time, “Joker” actor Jared Leto went full out for Met Gala 2019. He posed with a replica of his own head, with near-exact matching head and facial hair.

Hollywood Out There Looks New 19
Image: Standard

Made by Gucci, the fashion house explained that this costume expressed “the work of a designer – the act of cutting, slicing, reconstructing materials and fabrics to create a new personality and identity with them”. Either way, this grotesque display will be a hard one to forget any time soon.

Tracee Ellis Ross Uses Her Outfit to Address Race Issues

Actress and comedian Tracee Ellis Ross used the Met Gala’s 2019 theme to highlight race issues, specifically people of color’s experience of camp culture and impact on it. She posted on her Instagram a picture of her and Lena Waithe with the caption “reclaiming the narrative.”

Hollywood Out There Looks New 17
Image: Hypebae

Ross wanted to focus some attention on the often over-looked impact that black people have had on queer fashion. She worked with Karla Welch to frame herself as the work of art for the evening, with Welch adding “it’s how we make ourselves art. For me, camp is a vessel for art, and we took that into consideration. Also, a woman is a piece of art, so there’s something there as well.”

Cher: The Pioneer of Brave Red Carpet Looks

Someone who laid the groundwork for celebrities in daring outfits was nation-beloved Cher, who usually turned up in an outlandish design to high profile events. Here she pictured at the Oscar Academy Awards in 1988 Los Angeles, where she won as best actress for her role in Moonstruck.

Hollywood Out There Looks New 25
Image: Vogue

Reminiscing about the night, Cher recalled, “I was dating [producer] Josh Donen, and I kept saying to him, ‘No matter what I wear, will you be OK with me?’ He kept saying, ‘Yes, sweetheart.’ Oscar night, I walked out in my outfit, and I thought he was going to pass out. When Jane Fonda saw me, she just laughed like crazy.” Like we said, a pioneer.

Solange Looks Holy in Latex

The amazing sculptural dress piece worn by Solange for the 2018 Met Gala was a standout outfit, not least because of its unusual shape. Working with
Iris Van Herpen, this statement dress was made in shiny black latex, with thigh-high boots to match. As Solange said herself, “I feel heavenly in black.”

Hollywood Out There Looks New 15
Image: Pop Sugar

Her choice to wear a du-rag under the halo headpiece was not a decision she made alone, using Twitter’s poll feature to ask her followers which out of three options she should opt for in wearing her halo crown. The fans chose and she followed through – combining the du-rag and halo was most favored and she looks glorious wearing it.

Ryan Murphy Honors Liberace in Pearls and Sequins

Another Christian Siriano design, but not split down the middle this time, is this entirely sequined and pearl-encrusted suit and cape. The writer and producer channeled the one and only Liberace for Met Gala’s 2019 camp theme, with the cape and hood weighing over one hundred pounds and requiring 5 pairs of hands to get it on.

Hollywood Out There Looks New 18
Image: Business Times

Taking heavy influence from Liberace’s costume as King Neptune, Murphy did enlighten us on some of the difficulties they faced transporting the outfit to and from the venue: “It was literally hell – I had to lie down in the car.” So no, it wasn’t exactly the easiest of looks, but what a spectacular entrance he made.

Cardi B Had an Entourage for Her Dress This Year

For the Met Gala this year, it’s reported that rapper Cardi B had an entourage of ten following her around to look after the giant train of her ruby encrusted gown. Designer Thom Browne collaborated with Stefer Jewelry to embellish her headpiece and bodice in $250,000 worth of rubies.

Hollywood Out There Looks New 24
Image: Glamour

Designer Browne said of his inspiration, that “I designed this dress for Cardi specifically because she has the ultimate beauty in a woman’s body, and that is what the dress is about for me: taking advantage of that beauty.” We can see what he means – the ripples throughout the dress accentuate her curves beautifully.

Billy Porter Channels Ancient Eygpt

Billy Porter had one of the best entrances at this year’s Met Gala, being carried in on a day bed by six topless men. Fashioned by designing duo “The Blonds”, Porter wore a gold-fringed catsuit with ten-foot wings, accompanied by gold-leaf shoes and a 240-karat gold headpiece.

Hollywood Out There Looks New 23
Image: Time Magazine

Porter praised The Met Gala for their theme this year, explaining “What I love about having it at the Met Gala and contextualizing camp, is it brings honor to a word and genre that can be discounted very often or thought of as cheesy. When it’s done properly, it’s one of the highest forms of fashion and art.”

Elvis’s Tribute to His Gold Lamé Suit

Many will be familiar with the cover of Elvis’s LP featuring him, in a gold-leaf lamé Tuxedo from the late ’50s. Despite its iconic place in pop history, it was rarely seen, having been assumed that it was either too uncomfortable for Presley to perform in, too hot to wear, or creased badly on him.

Hollywood Out There Looks New 4
Image: Pinterest

In 1968 however, Elvis made an appearance on the “Comeback Special” in a gold sequin jacket (pictured). It’s said to be his tribute to his original iconic look over a decade before, having been approved for personally when approached by the designer: “After Belew [the designer] dropped the gold pants in favor of black ones and showed Presley the proposed jacket fabric, Elvis said, ‘Fine. I’ll go with that.'”

Jordan Roth Wore an Optical Illusion

Four-time Tony award-winning producer Jordan Roth is a theatre owner and overseer to five broadway theatres, which we can see became the major inspiration for his gala look this year. The outfit is an optical illusion, as when Roth’s arms are down at his side the design looks to be a closed theatre curtain. As his arms rise, the theatre hall is unveiled, like a theatre curtain rising.

Hollywood Out There Looks New 21
Image: CR Fashion Book

Designer Iris Van Herpen said that along with Roth, they “talked about the concept of camp and about exploring the camp of theatre. Part of Jordan’s briefing to me was: ‘Put a proscenium around anything, raise a curtain in front of anything, and it becomes performance.’ The look explores the relationship between the fine line of performance and illusion and transforms Jordan into a performance himself.”

The Makeup Look That Gives You a Headache

Star of Fantastic Beasts and Where to Find Them and Justice League, Ezra Miller strayed from the norm with his dizzying makeup reveal. Makeup artist Mimi Choi created the illusion, having already established herself as an expert in optical illusion makeup artistry, choosing to focus on extra sets of eyes.

Hollywood Out There Looks New 22
Image: Vulture

Miller wore a Burberry suit with a rhinestone-embellished corset, originally walking out with a mask and cape before revealing himself underneath. Embracing the theme of the gala, Susan Sontag’s words on artifice and exaggeration seem particularly resonant with this look.

Rihanna in a Giant Gold Cape

In 2015, Rihanna set a new bar when she turned up in this insane yellow “empress” robe. Created by Chinese designer Guo Pei, it weighed a hefty 25kg and featured a 16ft long train, all of which took over 50,000 hours of labor to create. It sported fur trimming and floral embroidery and was the product of two years’ work.

Hollywood Out There Looks New 20
Image: Vogue

Rihanna told Vanity Fair in 2015, “I’m so in love with this dress, but the train is insane! I can’t really walk in it without any help – but it’s so worth it.” She found the dress and Guo Pei, China’s first Haute Couture designer, on the internet after searching for Chinese couture.