25 of the best-dressed musicians of all time

Michael Jackson always embodied an effortless level of cool, and he knew just how to make any garment a style of his own. The King of Pop fancied military-style jackets, leather jackets, cropped pants, chunky belts, a single sequined white glove, and hats — to a point in which fans all over the world would try to emulate his style in any shape or fashion. His looks always seemed to be inspired by art and history — in a way, his style was paying respect to both. He may be known as the King of Pop, but also easily could’ve been named the King of Style as well. 

Rihanna is the type of artist who doesn’t follow trends; rather, she sets them at a high bar for people to follow her. From her fashion in her music videos, to her red-carpet looks, to a night on the town, Rihanna is never afraid to take risks and turns heads wherever she goes. Whether she’s wearing a see-through gown, a puffer jacket with a sleek heel, or taking her maternity looks to another level of cool, it’s no wonder people look forward to seeing her looks at the Met Gala every year. In 2014, the Council of Fashion Designers of America (CFDA) honored Rihanna with the Style Icon award. 

David Bowie wore whatever he wanted to, and looked good doing it. He could rock anything, such as leather jackets, monochrome suits, floral prints, one-legged bodysuits, mini dresses, feather boas, and everything in between. It’s no wonder that he and his wife Iman were a fashionable power couple. Bowie was always well aware of how fashion is a form of self-expression, he easily changed how people viewed rock stars, and influenced fashion designers with his style.  

If one thinks about how women rappers showcase their fashion style today, they have Lil’ Kim to thank for it. Kim was never afraid to be a bit risqué with her looks, and she always kept people talking. Kim was notorious for blending femininity, sensuality, and fabulosity with hip-hop, making the genre more high-fashion. When other women rappers were incorporating more sport and street looks, Kim was giving ultra-feminine such as fur coats over a bikini, colorful wigs, and sleek silhouettes. It also helped that her stylist, fashion designer Misa Hylton, was her right-hand woman helping her to bring every look to life. 

Prince is the type of style icon who pushed boundaries and truly didn’t care about any opposing opinions. People tend to have their own ideas of how men and women “should” dress, but Prince always did things his own multifaceted way, and looked good doing it. Styles that may be deemed outlandish to some people, were just effortless for Prince. He could easily rock a suit, high heels, a lace blouse, ruffled tops, and pants with the backside cut out — the Purple One was never afraid to push the envelope. 

Gwen Stefani is the definition of a blonde bombshell who can pull off any look effortlessly. When she was a member of her band No Doubt, her style was more tomboy with a little bit of femininity, such as a crop top with baggy pants. But over the years, Stefani has taken her style to new glam levels with more dresses, pantsuits, heels, and boots. To this day, she can still rock a tomboy look, but she brings a lot more chic elements to it. She’s more than “Just a Girl” — she’s a style queen who embodies cool. 

There’s a reason why Diana Ross is also known as The Boss — also the title of her tenth solo album — because when she walks in a room, she completely owns it. Whenever people see Ross, she will always be seen with larger-than-life curly hair, a luxurious gown, and full-on glam. Her looks are always classy, chic, fierce, and elegant, and they’ve been that way ever since she was a member of The Supremes. From shimmering dresses, to a steep stiletto pump, to batwing sleeves, to dramatic eye makeup, Ross is the queen of being a showstopper. 

André 3000, also known as one-half of the hip-hop duo OutKast, has always kept his style bold, colorful, and eclectic. Not to mention, there are plenty of times when André used his outfits to make a statement and call for change. He was always the more experimental group member with his fashion style. People just never know what they’re going to get when it comes to his fashion. He’ll rock a silk suit, a blonde wig, pants with suspenders, football jerseys, and dashikis. No matter what he wears, André always embodies how comfortable he is in his own skin. 

Madonna may be known as the “Material Girl” (in which she channeled her inner Marilyn Monroe), but she always makes sure to give the world some fashionable moments. Decades later, people still talk about her “Like A Virgin” music video, in which she wore a wedding dress with a belt that read “Boy Toy” on it. Madonna knows how to rock anything such as pantsuits, dresses, trench coats, leotards, and the iconic Jean Paul Gaultier bustier. She knows how to dress for different styles such as punk, military, and elegance. 

Jimi Hendrix was the type of artist whose style was always a sign of the times. He wore garments such as fringe jackets, floral tops under a suit, bell bottoms, hussar jackets — a classic style with psychedelic realness. Colorful, vibrant, yet cool — that was the Hendrix way. 

One word that comes to mind when people think of Frank Sinatra’s fashion sense: debonair. Since he would mostly wear tailored suits, tuxedos, and fedora hats, his look always came across as sophisticated, sharp, and suave. Sinatra embodied a classic look of a crooner that people think an artist like him would dress like. Just like his famous song “My Way,” Sinatra always did fashion his way, and set a standard for other artists to follow. 

Little Richard always knew how to make his flamboyant style look cool, chic, sleek — and as a pioneer of rock ‘n’ roll, he had a number of artists emulate his sound and looks. In addition to his stylish fashions and thick pompadour hairdo, he always made sure he had a make-up look to match. Richard didn’t conform to societal norms and would rock bedazzled suit jackets, crop tops, and everything in between. A lot of Richard’s looks were criticized and weren’t as accepted as they are in the world of music and fashion today. But it was also Richard’s self-confidence that always stood out more than anything.

Rock band Kiss is not only iconic for their music, but it’s their image that always stood out. Each member rocked a black hairdo, would paint their faces with Joker-style make-up, and black and silver outfits that gave space-age realness. Kiss was the type of band that truly embodied the glam rock era. Although Kiss briefly ditched the costumes and makeup, their classic look is always remembered in their artistry. 

James Brown may be known as the Godfather of Soul, but he also showcased fashionable moments that some artists still emulate to this day. He wore tailored suits, pointed shoes, oversized capes, flared trousers, and a high pompadour hairdo that artists like Janelle Monae and Bruno Mars would envy. Brown always kept his looks sharp, yet extravagant, giving him a level of smooth swagger that people loved. 

By now, people should know how much Beyoncé stops the world, not only with her music, but with her fashionable looks. Her group of fans, known as the BeyHive, are always anticipating what she'll wear in her music videos, on red carpets, at award shows, even attending a NBA game — and she serves a look every single time. She knows how to bring glamour, sexiness, sportiness, and even pays respect to designers who deserve their flowers. For the Juneteenth show of her 2023 Renaissance World Tour, she made sure that every look she wore was created by a Black designer — a great way to pay it forward in a fashion industry that isn’t always diverse. 

Elton John always knew how to shine behind a microphone and a piano, but his musicianship wasn’t the only star of his show — his fashions also made a statement. John has always loved bold colors, prints, and glitter that helped him stand out on any stage. He’s the type of artist who makes other people feel like it’s cool to be yourself, and fashion is an expression of that. John’s fashions were known to be extravagant, embellished, flamboyant, and eclectic — he also always made sure to have a signature pair of sunglasses with every outfit. Whether he wore a suit with bell bottoms, a sequined Los Angeles Dodger uniform, feathers, or leather, he always showed up with unique taste. 

Lenny Kravitz is a rock ‘n’ roll fashion killer, who brings a smooth level of cool to his looks. Back in 2022, Kravitz was honored with the CFDA Fashion Icon Award, and if one looks back on his stylish looks throughout his career, they could see why the honor was long overdue. He’s known for rocking dark sunglasses, leather, and bold prints that make him a standout. Kravitz can give chic, but he can also make it rock ‘n’ roll, it gives a certain level of aura about him that’s very endearing. 

Some of the styles that people see on today’s rock and pop stars, more than likely Mick Jagger channeled it decades ago. The Rolling Stones frontman would wear whatever he wanted to, such as wide-sleeved tops, bedazzled jumpsuits, one-shoulder tops that bared his chest, crop tops, and over-the-top collars. No matter what we wore, he knew how to make it eye-catching but still effortlessly stylish. 

Usher, the reigning King of R&B, can pull off any look, any color, in any style — and people love it. He doesn’t always necessarily go with an eccentric look, but he knows exactly which type of accessories can enhance a look (such as sunglasses or his signature U-chain), he knows which colors he looks the best in, he pays homage to his idols (i.e. Michael Jackson and Fred Astaire), and at times he brings a sprinkle of his hometown Atlanta to his look. Since Usher is a performer, whatever he wears on stage always needs to have some breathing room so he can hit his iconic dance moves (like the handstand from the “U Remind Me” video).” 

Throughout his career, Bob Dylan always had a chill and modest style to his look. He kept his style pretty minimalistic, but at times would have a more daring look. He would rock anything such as leather jackets, blazers, button-down shirts, jeans, cowboy boots, and sunglasses. Dylan always came across as an artist who wanted to show a classic, yet comfortable look.

Run-DMC told everyone to “Walk This Way” as they showcased their New York and b-boy looks at the forefront of hip-hop. Known for rocking Adidas shoes all the time, the look became a big marketing tactic for the sneaker brand. So much so, Adidas ended up signing Run-DMC to a lucrative endorsement deal, making it the first deal of its kind between hip-hop artists and fashion. But their look was more than just the sneakers, it also included athletic track suits, hats, oversized glasses, and gold chains.

When Pharrell Williams first came onto the scene as one-half of the production duo The Neptunes, his fashion style was very hip-hop. It was t-shirts, trucker hats, beanies, tracksuits, jewelry, and tennis shoes. However, as he progressed in his career, he experimented more with his look. Now, his style isn’t just boxed in, but more eclectic with looks looks such as suits with shorts, fringed sweaters, bold prints, and his iconic Vivienne Westwood hat. In early 2023, Williams was named as creative director for Louis Vuitton menswear. 

Simplicity is key when it comes to The Ramones and their fashion sense. They never had to overdo their look and kept their style very minimalistic. As rock stars, they felt they only needed some ripped jeans, a t-shirt, Chuck Taylor sneakers, a leather jacket, a shaggy hairdo — and they were good to go. They knew just how to pull off punk rock realness that other bands would imitate to this day. 

Teddy Pendergrass could wear anything, and it always embodied different levels of chic, classic, and cool. He knew just how to keep his look sexy enough for fans to fawn over him. Whether he was wearing a tailored velvet suit, a long fur coat, or a tracksuit, he reflected a certain level of sexy that played into him being a soul and R&B heartthrob. There’s no doubt about it that other R&B artists that came after him definitely took inspiration from his style.

Throughout Elvis Presley’s career, he adorned himself in a number of looks that showcased his levels of style. Presley could rock a nice, tailored suit, a leather jacket, or even a high-collared, bedazzled jumpsuit (which is still a favorite look among Elvis impersonators). Even when Elvis wore outfits that were deemed flashy, he knew how to make them look cool.