Historically Most Stylish Black Men: 8 Dapper Dons Who Were Made in the Past

Historically Most Stylish Black Men: 8 Dapper Dons Who Were Made in the Past

Let’s face it, men of the former years had exceptional taste. Heading out for a stroll down Madison Avenue called for a double-breasted jacket, titled derby and the cleanest pair of wingtips your closet housed. Refined style came with the territory of being a man—it was in your biological makeup—fashion DNA. And in our humble opinion, the colored brothers back then added a little something extra to their retro looks.

Who could forget Billy D’s dictator mustache? Or Sammy Davis, Jr.’s impeccable suits.  Bump the rappers and entertainers of today, it’s the unsung style pioneers of yesteryear who wrote the handbook for how a respectable man is supposed to dress.

Dapper dons were made in the 20s and 30s, groomed in the 40s and 50s, paraded their swag throughout the 60s, 70s and 80s, and at the brink of the 21st century, cooled down and let the younger fellas live. Join us in celebrating the iconic style of 8 distinguished gentlemen who were made in the past.



Billy Dee Williams


The $ex appeal of pretty boy Billy, shined through whatever he put on. Mr. Colt 45 was such a ladies man!



Sammy Davis, Jr.

Rat Pack member and full-out entertainer, Sammy Davis, Jr. had impeccable taste. From the popped fur collar (above) to the vintage Gucci tote (below) , the slender Harlemite was clean.  

 Bonus: Sammy was the first African-American to grace the cover of GQ (September 1967)


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Marvin Gaye


Smooth melodies were just a fraction of what this Motown visionary had to offer. Super Fly. Need we say more?

Bob Marley

Yes—we know—he burned green and wore a head-full-of-dreads, but it’s the late Bob Marley’s simplistic style that we’re celebrating right about now. From khaki military shirts to red, gold and green tams, Bob’s disheveled rock ‘n’ roll fashion was just as comfy as it was cool.

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Malcolm X

What’s one of the first accessories that come to mind when you think ‘Malcolm X Style?’ It better be browline glasses! His headwear, neckwear, outerwear, and scruffy goatee spoke volumes, however, the ever-so-popular Ray-Ban esque frames he put on the map circa 1960s, are a modern-day style staple.



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Harry Belafonte

 Calypso singer, civil rights activist, but first and foremost, Caribbean man to the core. Undone dress shirts were signature Harry Belafonte style and when he covered up, a suede overcoat and houndstooth pants were a probable option.



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Teddy Pendergrass


Teddy’s gusty baritone defined 1970s R&B seduction. His sharp style and passionate performances made ladies want to “Turn Off The Lights.” Honestly, what other man can pull off white cowboy boots? Classic.

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    Teddy P. was the man……Gordon Parks, he was a very distinguishing looking gentleman…

  • Marco

    Right on, momma, but look here, you forgot my man Walt Fraizer. Ya see, this cat Walt was a baaad mutha–shut yo mouth!! We’re not talkin’ bout some square, jive time turkey here, can you dig it?? Walt had all the foxy ladies. This brutha was a cooool cat, outta sight, dyno-mite…now tell me momma, can you dig it??

  • Naki O

    Gregory Hines!!!

  • Danceroflife

    Gregory Hines, Bob Marley and Marvin Gaye.  

  • Danceroflife

    I forgot to add Malcom X  

  • monitorette

    Gorgeous Men, great style, Class, Presence, Not a Single Show Off attitude.
    To all the Jay Zs & Kanyes of the world: Take Note!


  • MIMI215

    OMG, I attended a show during his last tour, I’ve always loved Marvin Gaye, and to see that man on stage in silk pajamas, Father GOD, take me, I was truly in heaven. Hurt my heart when he died.

  • blackizbeautiful

    Lawd they were FIONE!!!!!

  • What about Issac Hayes and Smokey Robinson? Back in the Day….Smooth.

  • artist_formally_known_as_cWj

    Marley’s way of presenting himself was not “rock and roll fashion”. Those khaki military shirts were likely more a reflection of the style of a certain East African emperor.

  • Duq

    How could you leave out Miles Davis and include Sammy Davis Jr.?

  • justsayin’

    What about Sidney Portier? “They call him Mr. Tibbs!!”

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