Hip Hop and R&B’s Top Dressed..Old School Edition

Article written by: Andre Sanchez
Posted on: June 3, 2009

When you think of old school, who comes to mind?

Keith Sweat?

Aaliyah?

Kris Kross? (i hope not)

Here’s the list for Hip Hop and R&B’s best dressed from wayyyyy back..will your favorite artist from yesteryear make the cut?

Mind you this was 10-20+ years ago. Our definition of best dressed is contextual to the era and not necessarily what has stood the test of time (as you will see).

In random order:

10. Rakim

A period dresser mostly, he still took his style to new places at a time when hip hop was about self-awareness and beginning to embrace afro-centrism. Rakim was still and always will be a hip hop fan’s source of intellect and introspection, but how Rakim presented himself as one from the hood made him that much more likeable (remember “know the ledge”)?

9. The artist formerly known as…

Prince

Prince goes from ruffles in his shirt in Purple Rain, to suave and sophisticated as seen here. If he’s not in some sort of best-dressed list, something’s wrong.

8. De La Soul (and most of the Native Tongues posse)

Here folks, is when a very interesting time in hip hop started. De La Soul dressed for a particular purpose, named their songs for very particular reasons (though cryptic to some), and with their D.A.I.S.Y age message they were pushing peace and self-realization around the same time that Public Enemy was  shouting protests from speaker boomboxes all over. Though De La wasn’t received too well at first, and only understood in some circles, their debut “3 Feet High and Rising” has since been lauded as a hip hop (and popular music) essential.

7. A Tribe Called Quest

Lots of the Native Tongue posse in full effect on this list! A Tribe Called Quest had one of the strongest visual identities in hip hop. As three black men trying to find their unique place in hip hop and what it stands for, its easy to see they kept the formula simple, stood out when they had to, and let the music speak. Sometimes, A good t-shirt and a great pair of jeans are all you need; it’s almost always more about what you do than how you look doing it.  Susan Boyle is a good example of that…ha!

6. Ghostface Killah

I know he’s not necessarily old school..but let’s face it, in the 90’s he was killin it! Ironman, Cuban Linx..he definitely had an impact on one particular item I’ll possibly be writing about soon: the Wallabee.

The distant cousin of the Timberland boot, The Wallabee (offically known as the Clark Wallabee Boot) first hit the scene in 1965 when Lance Clark sketched out a  moccasin built and inspired by nature to create the world’s first comfort shoe. Talk about old school. Ghostface and Method Man swear by em, and rap about them all the time… must mean somethin’!

Now let’s have some fun…these next five probably are not in your list, but if you had to make them over, how would you?

5.  Michael Jackson

4. Ol’ Dirty Bastard (RIP)

3.  Da Brat

Playing for the OTHER team now…SMH

And for this next one..thought I’d toss a question to you readers. If you could say anything to:

2. Jermaine Dupri (you saw his new “Janet Jackson as a saint” tattoo, right?) SMH

What would you say?

1. Soulja Boy: Where to start.