7 Classic Hip-Hop Fashions That Would NEVER Hold Up Today

MC Hammer Performs In Minnesota
Photo: Getty Images

Fashion and hip-hop are linked together like the Fourth of July and hot dog-eating contests. And while some legendary rappers put their stamp on timeless trends (for example, Run-DMC with Adidas), others have not fared as well. Here, we look at some items more likely to end up in a Salvation Army dumpster than on the backs of today’s dopest MC’s.

1. Cross Colours

cross colour hoodie OUTOFSTEP DOT NET
Photo: OutOfStep.net

One of the first designer brands of hip-hop clothing, Cross Colours were hugely influential, but would fade away due to a surge of competing brands and, probably, the fact that kids no longer wanted to look like a flag at the Olympics.

2. Backward Clothing

Kriss Kross backwards FASHIONBOMBDAILY DOTCOM
Photo: FashionBombDaily.com

Sadly, we recently lost Chris Kelly, one-half of the teen hip-hop duo Kris Kross. While revolutionizing seventh-grade dances in the early ’90s, Kris Kross also paved the way for kids everywhere to wear their clothes backwards and panic like a lost dog when they had to go to the bathroom.

3. Baggy Pants

Photo of MC HAMMER
Photo: Mick Hutson/Getty Images

MC Hammer ushered in the ’90s with pants so baggy, it looked like he’d deployed a parachute. Seriously, guys wore this s*** while attempting to pick up girls. How far we’ve come…

4. Starter Jackets

Starter jackets TUMBLR DOTCOM
Photo: Tumblr

Nothing says “cool” like hats and jackets that make you look like you’re about to go fishing. Hip-hoppers proudly displayed this sports-affiliated clothing line, but we couldn’t understand why anyone would proudly show off logos for the Jets, the Hornets or any team from the NHL.

5. Gangsta Looney Tunes T-Shirts

Hip Hop Looney Tunes BLOGSPOT DOT COM
Photo: Blogspot

Nothing to see here. Move along. Let’s go…break it up, break it up….

6. 8-Ball Jackets

8-Ball jacket RAPGENIUS DOT COM
Photo: RapGenius.com

8-Ball jackets were so popular, kids were getting shot for them. We understand the urge to resurrect these jackets with a hint of irony, but we plead with you: DON’T DO IT, MAN! (Not because you’ll get shot…because everybody will be too busy laughing at you to wanna hurt you.)

7. Overalls

The Fresh Prince of Bel-Air
Photo: NBC via Getty Images

Want to nail the look of a farmer with rhythm? Simply throw on a pair of overalls. Bonus points if you click off one of the straps. We still scratch our heads at this easy-come, easy-go fashion trend, but it seemed to sweep through hip-hop strongly enough for even 2Pac to give it a shot.

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RG Daniels (@RGDaniels) is a comedian and writer in Brooklyn, NY.