20 Iconic Celebrities Who Ripped Up The ‘Rule Book’ By Wearing Whatever They Wanted

So many celebrities grab the latest fashion trend straight from the runway and wear it on the red carpet. But these stars aren’t really bending style rules – they’re conforming to them. Yet there are some A-listers – including these 20 – who aren’t afraid to go off the beaten path, stylistically speaking. And we love them for being themselves, no matter what. So get ready for man-skirts, harlequin jump-suits, rain jacket dresses and super inflatable puffers!

20. Jaden Smith

Jaden Smith’s decision to wear skirts on the red carpet was not meant to draw attention to himself – apparently. No, he wanted to take the heat off of kids who chose to do the same. He explained to Nylon in 2016, “I’m going to take most of the blows… in five years when a kid goes to school wearing a skirt, he won’t get beat up and kids won’t get mad at him. It just doesn’t matter.”

Smith’s forays into fashion trend-setting haven’t started and ended with skirts, though. The actor-musician has no fear when it comes to color, either. Check out this look if you need proof: he has matched his candy pink hair to the chain around his neck and the grill in his mouth.

ADVERTISEMENT

19. Freddie Mercury

Freddie Mercury wrote some of the best-ever progressive rock songs – “Bohemian Rhapsody,” anyone? But the trailblazing musician didn’t just break the mold for what producers thought was required of a hit song. He also stepped out in some of the best clothes of his time, including this oversized rainbow-colored coat, which he wore with white pants and no shirt underneath.

Yes, Mercury needed wild outfits that complimented his larger-than-life on-stage persona. And he was doing this before the 1980s, too. In 1975 he slipped into this number, a checkered, long-sleeved jumpsuit with a very deep U-neck that hugged his lanky frame.

ADVERTISEMENT

18. Marlene Dietrich

Nowadays we wouldn’t flinch if we saw a Hollywood actress appear on-screen in a tuxedo while pretending to be a man and kissing another woman. But in 1930 this was headline-making stuff, and it was Marlene Dietrich who made this move in her American film debut. Obviously she wasn’t scared of taking risks in art or in fashion.

ADVERTISEMENT

Dietrich’s liking for menswear-inspired fashion became clearer as she spent more time in the spotlight. It was more than just the fact that she was bolder than her peers, though. The actress had openly declared her bisexuality at a time when people simply did not offer up such information. So her suits – like this bold, purple one – were a way of subverting expectations, as she always had.

ADVERTISEMENT

17. Michael Urie

Michael Urie could have worn a suit to the 2019 Met Gala. He could have even worn a dress. Instead, he chose to make a major statement in this Christian Siriano design that’s half pink tulles and frill, half pinstripe suit. When the designer shared the look on his Instagram, he wrote, “You can be your own prom date no matter who you are!”

ADVERTISEMENT

Not all of Urie’s looks are as camp as the Met Gala one – of course, that was the theme of the event that year. But the Ugly Betty star still foregoes the traditional dark-colored suit and white shirt for patterns and colors that set him apart from the pack. When’s the last time you saw someone on the red carpet in a zebra-striped suit?

ADVERTISEMENT

16. Lil Nas X

Lil Nas X burst onto the scene in 2019 with his song “Old Town Road,” which became the longest-running number one song in Billboard history, sitting atop the charts for 19 weeks. But style experts saw him as more than just a musician. W magazine said he was “redefining masculine expression” that same year. You can see how he might be in a hot pink cowboy getup like this one.

ADVERTISEMENT

Clearly Nas likes bright colors and bold patterns – here, he’s wearing heels, too. He later told Variety that this was, “the craziest outfit [he] ever put on.” But the lime-green-and-zebra-print look, which he wore to the American Music Awards in 2019, got him plenty of airtime. He said, “Whenever they panned to the audience, I stood out.” Surely not!

ADVERTISEMENT

15. Annie Lennox

Slipping into a powder blue bolero jacket, tying a black ribbon around her neck and topping it off with a leather beret? Says Annie Lennox, that and the rest of her fashion choices were neither planned nor intentional. She told Stylist in 2012, “It just comes to me. I can’t explain the actual process of why I would want to wear a sailor’s hat covered in leopard skin.”

ADVERTISEMENT

Lennox did have something of an explanation for this plaid suit she wore in the early 1980s, though. She said, “I loved the tailoring at the time of the eighties suits with padded shoulders and nipped in waists. It looked […] cutting edge.” The singer gave no reason for choosing the fluorescent orange hair, though. She could almost fool us for Batman’s Joker.

ADVERTISEMENT

14. Cee-Lo Green

Cee-Lo Green’s style is just about as funky as his music. Here we see the “Forget You” singer rolling up to the Gateway for Cancer Research organization’s Studio 54-inspired gala. He wasn’t shy to adhere to the night’s theme, either, wearing head-to-toe sky blue sequins and golden platform shoes.

ADVERTISEMENT

A different pair of heels – and an equally funky outfit – came out when Green performed at the 2020 Soul Train Awards. He paired a pair of orange leather bell bottoms with a belted vest in the same hue. If that’s not enough, then take a peep at the accessories, which include a pair of bedazzled glasses.

ADVERTISEMENT

13. Blake Lively

Lots of ladies on our list are suit fans. Blake Lively wore a slew of them on her press tour for her film, A Simple Favor, including this soft pink get-up, complete with a mint green tie. But she said she drew inspiration for these looks from one of the men with whom she worked on the movie.

ADVERTISEMENT

Lively’s oversized plaid suit also fell into the same category of inspiration on the movie’s tour. So who was the guy who galvanized her to don menswear? She told E! News in September 2018, “This outfit is inspired by [A Simple Favor director Paul Feig] without even meaning to.” On the night she was interviewed, she admitted that she and her director had showed up in embarrassingly similar outfits.

ADVERTISEMENT

12. Harry Styles

Ruffles, a pearl earring, painted nails and a hand full of rings. That was Harry Styles’s look for the 2019 Met Gala – the same camp-themed soiree to which Michael Urie wore the boy-girl outfit. Although a touch more subtle, the “Adore You” singer played with gender by wearing soft fabrics with traditionally feminine detailing.

ADVERTISEMENT

Even outside of the Met Gala, Styles isn’t afraid to challenge the menswear status quo. It may all come down to the person who inspires both his musical stylings and fashion. He gave away her identity in a 2017 interview with Entertainment Tonight, saying, “I think both music and fashion, [my] main influence was probably Shania Twain. Yeah, I think she’s amazing.”

ADVERTISEMENT

11. Katharine Hepburn

Katharine Hepburn wore pants even before Marlene Dietrich did – and before she sported them in Hollywood. Because she was a child who coveted her brothers’ clothes. She told her biographer, Charlotte Chandler for the book I Know Where I’m Going: Katharine Hepburn: A Personal Biography, “I had a phase as a child when I wished I was a boy because I thought boys had all the fun.”

ADVERTISEMENT

By the time she became a famous actress, Hepburn’s clothing choices meant more than that. She wore slacks as a way to maintain her autonomy and her comfort, too. As journalist Mary McNamara put it in her 2003 eulogy of the actress, “Katharine Hepburn was the patron saint of the independent American female.” And a lot of that came down to the trousers she wore no matter what.

ADVERTISEMENT

10. Madonna

Critics didn’t love this outfit of Madonna’s. She wore it to the 2016 Met Gala and, while it’s ornate and eye-catching and risque on its own, things get even wilder when she turns around. You may guess how – a very sheer fabric covered her bum, leaving it more or less exposed on the red carpet. Of course, the singer couldn’t have cared less.

ADVERTISEMENT

It’s rare that Madonna wears something that doesn’t divide critics and audiences alike. And that’s precisely how she tears up the red carpet rule book. Here’s another perfect example, the time she wore a crown of thorns and layers of statement necklaces to the MTV Video Music Awards in 2018. Witch doctors eat your heart out.

ADVERTISEMENT

9. Ezra Miller

Ezra Miller has made no secret of who he is, both in and out of the spotlight. The actor is openly queer, and he has no qualms with switching up his gender presentation. Here we have him at the 2018 Parisian premiere of Fantastic Beasts: The Crimes of Grindelwald wearing a puffer-coat-style dress, matching hood and black lipstick.

ADVERTISEMENT

At Urban Decay’s stayNAKED launch event – which took place in Seoul, South Korea in 2019 – Miller slipped into something a little lighter. The actor paired a colorful oversized coat and matching shirt with simple black shorts. But he balanced all of that brightness with a pair of knee-high, lace-up patent leather heels, as one does.

ADVERTISEMENT

8. Dennis Rodman

He’s wearing a glittery cropped tank top, a pair of baggy jeans, hoop earrings and sunglasses. Dennis Rodman was onto something when he picked out his clothes for the 1995 MTV VMAs – the basketball player had mastered the trends of the 2020s long before this decade had arrived. He was ahead of his time in the fluidity with which he dressed, too.

ADVERTISEMENT

The more outfits of his you see, the more it becomes clear that Rodman had no problem bending the rules. This outfit, which features a sheer white blouse over a wrap-around black crop top, proves that point, too. And his daringness was rare in the 1990s. As GQ’s Jordan Coley put it in 2020, “Rodman was one of the handful of pop culture characters actually bothering to liberate himself from normative social constructs.”

ADVERTISEMENT

7. Barbra Streisand

Barbra Streisand could have worn a more conservative outfit to accept her 1969 Best Actress Oscar for the movie Funny Girl, but that wouldn’t have been very her. So she selected this sheer, sequined-covered feminine take on the tux, and explained why to W magazine in 2016. Streisand said, “I thought to myself, I’m going to win two Oscars in my lifetime, and I’ll be more conservative next time.”

ADVERTISEMENT

Streisand has remained a style icon throughout the course of her nearly six-decade career. It’s not hard to see why when you see this number, in which she showed up to London’s Heathrow Airport in 1969. She’s wearing head-to-thigh fur – including a giant ushanka hat – and an extra-large pair of sunglasses. If the latter was meant to hide her celebrity, well, we think it was a little too late for that.

ADVERTISEMENT

6. Jonathan Van Ness

Jonathan Van Ness shared his gender identity with the world in 2019 after wearing an outfit that was non-binary, just like him. Since then, he has made a point to wear, well, whatever he wants on the red carpet. This look was a glam turn for JVN: he wore the navy cowl-back dress with a retro wavy hairstyle.

ADVERTISEMENT

And at the Netflix Creative Arts Emmys After Party, JVN slipped into a hot-pink strapless frock but left his long locks down the back. It all suits the star, who explained his gender identity – well-reflected in his fashion choices – to Out. He said, “I just am either like gender-bendy or nonconform-y or nonbinary and some days I feel like a boy and some days I feel like a girl.”

ADVERTISEMENT

5. Celine Dion

Celine Dion could have walked the 1999 Oscars red carpet in this white suit and turned heads no matter what. The silky trousers, bespoke fedora and sleek sunglasses were already conversation starters. But when she slipped her jacket on backwards, well, she really made a fashion statement along the lines of, “I’ll wear what I want, how I want.”

ADVERTISEMENT

And Dion has only continued to reiterate that statement with her bold and eclectic fashion choices since. Here she walks the streets of Paris in 2019, wearing a dress that looks like it’s been cut from a rain jacket. Over it, she has on a grey blazer and, beneath it, she’s wearing chunky sneakers. It sounds disjointed but, altogether, it looks kind of amazing.

ADVERTISEMENT

4. David Bowie

David Bowie’s Ziggy Stardust era – and the incredible unitards and kimonos he wore throughout – helped create glam rock. Here he dons red overalls and a twisted crop top finished off with a neck scarf. As for the eye patch, he started wearing that out of necessity. Turns out the iconic singer had pink eye, so he wore the protective accessory for an interview, then fell in love with it.

ADVERTISEMENT

Kansai Yamamoto – a designer from Japan – put together many of Bowie’s Ziggy Stardust looks after learning that the singer had been wearing women’s clothes while performing. There’s a definite softness to his looks during this era. Take this silky jumpsuit as an example: It could work just as well as a ladies’ outfit.

ADVERTISEMENT

3. Grace Jones

Music. Movies. Fashion. Grace Jones has left her mark on all three creative fields, consistently captivating audiences with her talent, and of course, her one-of-a-kind style. Many of her most iconic looks are sleek and androgynous, much like this leather trench she wore at Chicago’s Park West in 1978.

ADVERTISEMENT

Of course, Jones also had fun with her fashion choices. This high-school-band-adjacent getup, which she wore to an NYC nightclub, featured teal and purple accents and a silky navy jumpsuit. But it was the hat that really turned heads with its white feathery mohawk running right down the back of it.

ADVERTISEMENT

2. Billy Porter

When Billy Porter plans to walk the red carpet, you pay attention. The singer-actor never shows up in anything simple or expected. Instead, he opts for gender-non-conforming fashion – this feather-trained white suit is a prime example. And when he does, he makes a statement: perhaps other male celebs should be as forward-thinking as he is.

ADVERTISEMENT

We could go on all day about Porter’s most stunning red carpet looks. His 2020 Grammys’ look had our jaws on the floor and not just because the bedazzled curtain on his hat opened and closed. The Pose star paired it with bright blue eye make-up, a diamond choker and a blue-sequined, bell-bottomed suit that had silver-hued fringe from the knee down.

ADVERTISEMENT

1. Elton John

No one has ever accused Elton John of being subtle, fashion-wise. For decades the singer has pushed boundaries with what he wears and where he wears it. This lacy hoop-skirt gown and glittering headpiece serves as just one of the seemingly countless examples of the singer saying no to the norm.

ADVERTISEMENT

Now considering how he dressed in the 1970s – as pictured previously – you may deem John’s more modern wardrobe to be tame. Even he has said that he, “can’t believe how sartorially crazy [he] was,” according to V magazine. Still, this shiny blue suit jacket is not something you’d expect the average person to wear, and that’s why we have come to expect from out-of-the-box style.

ADVERTISEMENT
ADVERTISEMENT
ADVERTISEMENT