LookBack: Diggy Simmons In Shocker $4,500 Leather Jacket! Really, Diggy?!

Diggy Simmons, son of Rev. Run of Run DMC, made his appearance as co-host on BET's 106 & Park this past Wednesday, and while he was lookin' great as the GROWN-UP boy from MTV's 'Run's House', he wore the popular CDG (Comme Des Garcon) 'Play' T-shirt for $125, Nudie Jeans for $225, and Air Jordan Retro 5 sneakers for $150.

Diggy's splurge stole the show, and that splurge was his $4,500 DIOR HOMME LEATHER JACKET. He seems to like to wear expensive jackets. He wore a $3,000 BALMAIN biker jacket to a fashion show once. I really hope that thing is on RENT. But the whole look is cool, anyway.

Now if it was me, I would be SUPER-BALLING for just 1/5 the cost of that DIOR jacket. I'm a guy who knows how to find deep discounts on some FLY-YY-YYY clothes and shoes.

Pic: Upscale Hype

Sneaker of the Day: Chivalrous Culture Hamachi Sneakers

These are seriously some HOTT sneakers. Chivalrous Culture teamed up with Diggy Simmons to produce this fine sneaker (Diggy is quite the 16-year-old businessman) for the masses. The sneaker has a red bottom like Christian Loubotuin, patent leather upper, and just has FULL-ON SWAG.

It will be released April 25th. The first 35 buyers will receive a limited edition bow tie. Hmm... niiiice.

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The sneakers look even better with the BOW TIE attached to it.

Pic: UpscaleHype

DIGGY SIMMONS Celebrates 16th B-Day Party In Swag Style (via MediaTakeout)

Well, I got all MediaTakeout pictures of Diggy Simmons' B-Day party. It was reportedly a LIVE one with the entertainment industry packing the place. Rev. Run and Justine gave Diggy a substantial amount of money...which he put into a bank account. SMART.

And Diggy had great style with his varsity jacket (probably Billionaire Boys Club), denim jeans with a Louis Vuitton damier canvas belt, and cool, simple blue hightop sneakers. 

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Cool diggs.....

In Daddy's Footsteps: DIGGY SIMMONS Lands "Freshman Class" in XXL Magazine

The Simmons family is definitely one powerful family. Which almost each member of the Run family doing something (Rev Run goes on tour and has his syndicated show, Justine's going back to singing, V + A have "Pastry" and other fashion projects, and IDK what JoJo does besides "Blackout"..), one of the youngest in the family is becoming known on his hip hop game.

DIGGY SIMMONS, the curly-headed boy on "Run's House' has grown up to claim his father's throne. He is featured on the cover of XXL Magazine (bottom left - dang, he looks a lot like my brother!) as one of the rising new hip-hop stars.

He looks cool, too in the all-black ensemble. Just my style, Diggy. Big ups to you! 

Pic: YBF