1. Sidney Poitier
Actor/ Director/Author
The Legend
One of Hollywood’s greatest leading men, Poitier will also be known as one of its most well-dressed. His trademark style is chock-full of tweeds, ties and tailored suiting.

2. LennyKravitz
Singer/Songwriter/ Actor
The Rogue Rocker
With a style nestled between lavish and laid-back, he effortlessly makes leather, denim, sunglasses, boots and loads of jewelry look sexy but accessible. You’ll find Kravitz in everything from vintage tees to rocker couture from designer Rick Owens.

3. Pharrell Williams
The Chameleon
From his trending-topic hats to his off-the-cuff wardrobe pairings—think Lanvin Bermuda shorts at the Oscars—this style phenom marches to his own drumbeat. And he is steadily building a legion of fans who mirror his eclectic fashion choices.

4. David Adjaye
The Minimalist
This stylish visionary takes a “less is more” approach to dressing, adding classic suiting and understated separates with immaculate cuts.

5. Kanye West
Rapper/Songwriter/ Producer/Entrepreneur
The Couture Connoisseur
Hip-hop meets high fashion with this showstopping performer, who has redefined what it means to be an artist today. Despite donning luxury brands including Balmain, Givenchy, Margiela and Dior Homme, he keeps gray T-shirts, designer sneakers and custom leather in heavy rotation.

Read more in the September 2014 issue of EBONY Magazine.