Totally Wicked: The 30 Best Dressed Musicians of All Time

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Who are the best dressed musicians of all time? Well that’s kind of a loaded question now isn’t it? It’s also a question that requires a little bit of thinking because there have definitely been a lot of artists who changed the game not just musically, but stylistically as well. In fact, with many of these musicians, some of their most iconic/memorable music moments are ones directly associated with a major fashion moment of theirs. Now if you’ve been keeping up with some of our previous “all time” lists, then you already know that our definition of “all time” is slightly different from others because in our opinion, all time means that you have withstood the test of time.

That in turn means that we tend to leave a lot of the “newcomers” off these lists (to be fair though, we do have a ton of emerging/new roundups that we put out), and the same is going to be true of this one. Our all time best dressed list is going to consist of the artists who check off the longevity factor. Check out our selections below.

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1. Michael Jackson

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The military outfits. The jackets. The fedoras, the gloves, and aviator sunglasses. The numerous leather pieces. Michael Jackson is simply the standard.

2. Prince

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Prince was always dressed to the nines, and you never saw him in anything other than his Sunday best. It’s also safe to say that Prince permanently adopted the color purple as many of his most legendary fits were ones where he wore that color. A true fashion legend.

3. Rihanna

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Rihanna still continues to have major (and viral) fashion moments eighteens years into her professional career, most recently with her Super Bowl halftime performance where she wore a red Alaïa puffer coat over top a red Loewe jumpsuit, and a pair of Margiela x Salomon sneakers.

4. David Bowie

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Known for popularizing “glam rock fashion,” David Bowie is an all time style icon as he challenged gender norms, critics, and societal expectations through his many looks, reinventions, and personas. Long live Ziggy Stardust. 

5. Robert Palmer

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One of our favorite things about Robert Palmer is the fact that he created some of the most “bang out” rock anthems ever between Power Station and his solo work all while wearing a… suit. The suits were always such an unexpected contrast with his music, especially when you consider the fact that his bandmates were oftentimes dressed in that classic 1980s rockstar look with the heavy makeup, fishnets, voluminous hair, etc. It’s so funny to see, and yet so legendary. And the suits were always on point too.

6. Jimi Hendrix

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Aka Mr. Cool. Who didn’t love the silk colorful blazers and bohemian style head wraps. Hendrix is another one that we lost far too soon, but he certainly made his mark while he was here.

7. Janet Jackson

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Listen. Janet Jackson had and continues to have eras. From the all-black and military looks sported during Control and Rhythm Nation 1814, to her iconic looks in Poetic Justice, Janet Jackson is hands down one of the best dressed musicians to ever do it.

8. Whitney Houston

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Whitney Houston certainly gets credit for being one of if not the greatest vocalist of all time, but in our opinion she continues to be underrated for her fashion looks. For example, you had the luscious curls and mauve dress that she wore in “I Wanna Dance With Somebody,” her 1990s looks were elegant and beautiful, and we can’t forget her new millennium reinvention with “It’s Not Right but It’s Okay.” Houston also proved that she can do sporty as well when she pulled to perform the national anthem in a…tracksuit. Yeah, Whitney is underrated.

9. Bob Dylan

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Don’t worry, our comprehensive piece on Bob Dylan’s style will be coming in the near future. In the meantime, let’s take a brief moment to appreciate how smooth and suave Bob Dylan’s style is with his blazers, trench coats, suede jackets, sunglasses, and pinstriped pants. Fashion killer for sure.

10. Madonna

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Madonna continues to be the ultimate rule breaker when it comes to fashion, and there’s no denying the fact that she has had some of the most groundbreaking style moments in music history whether it’s been through a video, performance, or red carpet moment. And she’s not letting up either.

11. Bob Marley

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Rasta Man Marley. As time passes, we continue to acknowledge his fashion impact even more with his retro sportswear, beanies, and laid back chill looks that matched his equally chill persona.

12. John Lennon

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There are people who still dress like John Lennon to this very day. The Ray Ban sunglasses that he often wore is something that is starting to come back in style, and his hipster looks remain copied. One of the best to ever do it both in music and fashion.

13. Andre 3000

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Andre 3000 has given us plenty of excellent looks over the decades (the “Hey Ya” video for example) and he has definitely reached the point where he deserves to be given his flowers as a style icon.

14. James Brown

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The Godfather of Soul gave us numerous moments of punk and funk with his flared trousers, glittery vests, and jumpsuits. We also have to appreciate his southern style as well with his waistcoats and satin suits. James Brown was never afraid to be James Brown, and we’d say he was quite good at it. 

15. Mick Jagger

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By this point we should all know that not only do we not have the “Moves Like Jagger,” but that we can’t dress like Jagger either. Hey, you can’t win everything in life.

16. Run DMC

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Run DMC is self explanatory. Their adidas tracksuits paired with the Superstars. The Kangol hats and the chains. The fact that they are the first major artists to ever land a deal with an athletic/fashion brand. Yeah, Run DMC are style legends for sure.

17. Jay-Z

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Jay-Z wasn’t lying when he said he popularized the Yankees hat, but he’s also been able to become a style guru outside of New Era with his many different suits and streetwear looks.

18. Beyoncé

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But Jay is always quick to tell you that his better half plays no games either. The cool thing about Bey’s style is that it has evolved a lot since her early days with Destiny’s Child. She’s definitely become more of a risk taker, and her fashion has become quite futuristic over these past couple of years.

19. Iggy Pop

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Iggy Pop’s musical style is a little bit of everything, so it makes sense that his fashion sense is a little bit of everything as well as he’s one of those artists who have been able to showcase a wide variety of looks. Sometimes Iggy will choose to forgo clothes altogether as he’s known to walk around shirtless. That’s just who Iggy Pop is.

20. Kurt Cobain

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The accidental style icon who helped make grunge and alternative style what it is today. Nuff said.

21. Jennifer Lopez

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Jennifer Lopez has been consistently consistent with bringing the looks over the years whether it’s on the red carpet or just casually running errands. She also has one of the most iconic red carpet looks of all time with that green Versace dress.

22. Eric Clapton

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Never too much. Never too little. Always even keel. That, our friends, is Eric Clapton.

23. Bruce Springsteen

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Our comprehensive style guide on Bruce Springsteen will be on the way soon as well because the man is a style legend. Period.

24. Tupac

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The bandanas. The baggy jeans. The nose piercing. The fact that he could still “dress it up and make it fashion” when he wanted to such as the 1996 VMAs when he wore a perfectly tailored suit. Pac was a real one.

25. Snoop Dogg

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A true West Coast California style legend (throws up the West Coast sign).

26. Biggie

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The man who made Coogi what it is certainly deserves a spot on this list.

27. Elvis Presley

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From the suits to the Vegas style costumes during the 70s, Elvis always delivered.

28. The Ramones

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The blueprint for 80s punk style.

29. Marvin Gaye

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R&B’s 007. The ultimate ladies man.

30. Stevie Wonder

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No explanation here.

Well these are our selections! Make sure to keep up with us for more style content and updates.

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