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The 15 Most Underrated Style Icons That Deserve Your Attention

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In the style world, we talk a lot about fashion icons. Of course you have the certified legends such as Rihanna, Audrey Hepburn, and Jackie Kennedy on the women’s side, and Michael Jackson, Prince, and David Bowie on the men’s side, but what about the style icons that are “underrated?” The ones that are flying under the radar so to speak? Well, that’s what we’re here to discuss today, the truly underrated style icons, both in the past and present. The people who constantly rock cutting edge fashion, but are overlooked when it comes to the many different “best dressed” lists that are put out on a yearly basis.

So now that begs the question of what is considered to be a style icon. In our book, a style icon means you have years worth of memorable looks to your portfolio. To be fair, you can’t really call someone a style icon if they’ve only been in the industry for a couple of years (even if they have a great sense of style). With that said, by our estimation, in order to qualify for this list, you need to have been in the industry for a minimum of ten years (and even that is slightly pushing it). Now that we have established our definition of what we think qualifies as an underrated style icon, let’s take a look at some of the best.

Sisqo

Janelle Monae

Justin Timberlake

Mary Kate and Ashley Olsen

Gene Kelly

Pam Grier

Green Day

Kool and the Gang

Avril Lavigne

Fefe Dobson

Robert Palmer

Gene Tierney

Usher

Coolio

Migos

RELATED: The 25 TV Characters With the Best Style, Ranked

1. Sisqo

Do you remember the days of male R&B groups? Those were the days. Sisqo was the lead singer and breakout star of the 1990s group Dru Hill, and to be honest, his style impact has always been underrated. Through the years, we’ve seen quite a few male R&B artists rocking the short blond buzz cut fade (Usher is currently wearing this look), but Sisqo was the first to do it on a national level.

And let’s not forget his legendary baggy leather outfits, gloves, and piercings either. Sisqo never disappointed when it came to his style, and he definitely needs to be appreciated more.

2. Janelle Monae

Janelle Monae is another celebrity that doesn’t get her just due when it comes to fashion appreciation. In this past decade, we’ve seen Janelle Monae challenge many fashion and even gender norms when it has come to her red carpet looks, performances, and music videos, which is probably one of the reasons why Prince, one of the all-time fashion legends himself, loved her so much because he too did the very same thing when it came to his looks. Janelle’s looks are sheer brilliance and full of creativity.

3. Justin Timberlake

Now you may be wondering if Justin Timberlake is underrated when it comes to his style. We feel he is because while he has solidified his place in music history both as a solo artist and with NSYNC, his fashion impact isn’t talked about nearly enough. Young Justin Timberlake represents early 2000s nostalgic fashion in the fullest, and he certainly had his fair share of mini-mes walking around in the years 2000/2001.

His music video style is under appreciated as well. For example, the videos for “Cry Me a River,” “Sexyback,” and “My Love” showcased great fashion for Timberlake. 

4. Mary Kate and Ashley Olsen

At first glance you might think that Mary Kate and Ashley Olsen aren’t underrated, but the truth is…they kind of are. While the two were certainly recognized as very fashionable in their teens, they don’t get as much credit they deserve in the present day because of how quiet they are. Nowadays you probably get a glimpse of MK and Ash once a year (if that), and you are lucky if they choose to take pictures at the events they attend.

Throw in the fact that they have no public social media accounts and, well, you don’t really see their outfits anymore. This has led to them being underrated at times in the style world, but make no mistake, Mary Kate and Ashley were killing the game in the 1990s and early 2000s as tweens and teens, and they can still very much dress their butts off.

5. Gene Kelly

When it comes to the old school actors of Hollywood’s heyday, we hear a lot about Fred Astaire, Cary Grant, etc., but not enough about Gene Kelly. Gene was just as smooth and suave as they were, and like Astaire, Kelly was also an excellent dancer. Mr. Kelly rocked the most dashing of suits and fedoras at all times, never looking anything less than an eligible bachelor. The actor’s style also aged gracefully, as he was as stylish at 70 as what he was at 25.

6. Pam Grier

Before there was Foxy Brown the rapper and Foxxy Cleopatra (the character Beyonce portrayed in the 2002 film Austin Powers in Goldmember), there was Pam Grier, the original Foxy Brown. In addition to the outfits she wore in films like Foxy Brown and Sheba Shayne, Grier established herself as a 1970s fashion icon outside of the big screen with her casual looks and photoshoots. A true funkadelic fresh soul sista whose style is still majorly referenced today.

7. Green Day

Can we throw a rock band in here for a second? Sure they are undisputedly one of the best rock groups of all-time, with Billie Joe Armstrong being recognized as one of the best musicians and guitarists to ever do it, but in our opinion, the group doesn’t get nearly enough credit for their style. There’s been so many cool moments from their duct tape photoshoot, all the way to their matching grunge style suits. And, of course, the American Idiot era alone was one for the ages. All hail Green Day!

8. Kool and the Gang

And since we’re talking about groups, let’s throw Kool & The Gang. If you recall, in September we did a style piece on Earth Wind & Fire’s classic hit “September,” and in that article we talked about the style impact of the group, but Kool & The Gang shouldn’t be slept on as well.

We saw them wear disco outfits in the 70s, and the Mr. “Steal Yo Girlfriend” suits in the 80s and 90s, and in case we still haven’t proven our point, these brothas paired cowboy hats with tracksuits. Never before had the world seen that, and never will we see it again.

9. Avril Lavigne

Avril Lavigne is a prime example of how to have a versatile signature style. She has never really strayed far away from the punk grunge look she has worn since debuting over twenty years ago, and yet her style has never become stale. We’ve seen Avril do punk rock, sexy punk, nerdy punk, even hip-hop punk, and to this day she is still very much “Avril Lavigne” style wise. Lavigne very much proves that you can have different variations of a set look.

10. Fefe Dobson

Fefe Dobson is another punk queen that has been giving us bold, sexy, and gothic looks on a consistent basis for over two decades. From the bangs, to the heavy eyeliner, and ripped shirt/jeans, Dobson remains a fashion queen. And while the grunge looks have certainly been her jam, she’s been known to wear a number of sporty looks too. The diversity has to be appreciated.

11. Robert Palmer

When all of his other bandmates were wearing the typical 1980s heavy metal looks that the rock groups wore back then, Robert Palmer opted for…a suit and tie. Watching old videos of The Power Station is a hoot because you have all the members of the band not named Robert Palmer blasting ear-ringing music rocking out on stage, and then there’s Robert, in a suit calm, cool, and collected.

The contrast is so unique that you can’t help but to have your eyes locked on Robert, and perhaps that was part of his genius both musically and from a style standpoint. Robert Palmer is also responsible for one of the most iconic style videos of all-time with his 1988 solo single “Simply Irresistible.”

12. Gene Tierney

We’ve mentioned this before, but Gene Tierney often gets overlooked when it comes to her actress peers from the same era. To be quite honest, Tierney had a tragic life that ultimately wound up shortening her career and time in the public eye, but when you look at her resume, she holds her own both with her film credits and the fashion she showcased in them.

Hopefully one of these days Tierney will get the full credit she deserves in the early Hollywood landscape because her influence has definitely been spotted in the decades since.

13. Usher

Usher is most definitely a style icon that needs to get talked about much more. In our opinion, the area where Usher shines his brightest fashion wise are both his music videos and stage performances because those are the places where a performer can sport multiple looks in one go, and Usher has had plenty of them. Some examples: The videos for “My Way,” “U Remind Me,” “U Got It Bad,” “Yeah” and “Caught Up” just to name a few.

Of course, everybody remembers what he was wearing in the music video for “Yeah,” with the blue Atlanta ball cap, the white jacket overtop a white tank, jeans, Air Force 1s, and the Usher chain. Nobody that was outside during that time will ever forget that look as it represented one of the greatest songs and albums in history.

14. Coolio

Long live Coolio. Coolio had a number of dudes dressing and wearing their hair like him in the 1990s, and if you thought it ended with the decade, we recently spotted somebody on a flight with the “Coolio” hairstyle (he had requested the hairstyle after Coolio’s passing as a tribute). That our friends is called generational influence.

15. Migos

And long live Takeoff. If you were anything like us, then you went back and binge watched a whole bunch of Migos videos upon learning of Takeoff's tragic passing. While we have always appreciated their style, what remains underrated is just how much they impacted the hip-hop style game, remaining true to their ATL roots while mixing other elements in.

Each individual member had their own unique style, and Take, in particular, was known for his mysterious style (which was a reflection of his personality), oftentimes only wearing dark shades. Now is the perfect time to start recognizing Migos as one of the most stylish rap groups of all time.

What do you think of our list? Agree or disagree? Make sure to keep up with us for more style content.

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