Diggy Simmons' Top 10 Sneakers of All-Time

Diggy Simmons just might be a mogul in the making. At 16 years old he has a budding rap career, and his own sneaker line (Chivalrous Culture) and he’s just getting started. Yup, like his uncle, his hustle is so Russell. Besides being one of the youngest rappers everyone is checking for (follower numbers don't lie), Simmons has always made his fashion sense a priority, and for a young’n has knowledge about kicks that even some the vets don’t. When Diggy stopped by Complex HQ’s a few weeks ago we sat down with him to talk sneakers—something he takes pretty seriously. Check out his top ten of all time, that includes everything from classic Jordans to high-fashion sneakers…

"Definitely, definitely incredible creatively — if you’re a sneakerhead or just love sneakers you’ve always had an idea about a sneaker or input, 'the laces should’ve been this,' you know anything, 'I would like this colorway on a sneaker' so being that I got to create [everything from] the silhouette to the colors, the detail everything that goes into making a sneaker — its definitely a cool opportunity to have my own sneaker line."

"Definitely a dope colorway for a Jordan. There aren’t many grey Jordans in general, but then the silhouette of the 11s I just love — they’re like a mid low top and its just dope. And I love the patent leather on the front."

"Another mid low top type of shoe, I love the detail on the sides — the two stripes where its red and how it comes together in the front."

"With the strap on the side. I love the stripes on the side and the different colorways that they’ve done. I think it’s a great overall sneaker — they pick great material for them as well."

"The Raptor VIIs are stupid. They’re incredible, I have two pairs, I have all black and the grey and black. Just classic. I love Air Jordan 7s in general; they’re just a dope sneaker."

"I have a bunch of different pairs — I have the ones with the wings on the side, the new ones with the wings on the back. Its just definitely creative, and Jeremy Scott always comes up with stuff that people don’t even think of. It was definitely a game-changer of its time and even now when Jeremy Scott keeps the ideas new and people excited and the way he's brought adidas to the forefront of our culture that we love is dope. When we think adidas it might not always be the coolest thing, but Jeremy Scott is dope."

"Who doesn’t love the Cement IIIs? Incredible sneaker, colorway is just dope, probably one of the most famous Jordans besides the Retro 1s. It just speaks for itself."

"That silhouette and design in general, and just to see that royal blue detail is just stupid. To see that red Jumpman and the white is definitely crazy. I love that sneaker."

"I’ve seen Android Homme, they’ve blessed me with sneakers from me wearing them by buying them. I saw Android Homme for the first time, like, their first colorways in '09, '08 on Hypebeast.com and I was like 'this is so dope.' It was that time where a lot of people were bringing high-fashion sneakers to the forefront and they were somewhat affordable but they were still dope and the quality was incredible. I love Android Homme as a whole, but the Android Homme Propulsion sneaker is dope."

"I wear these all the time; if I'm not doing something an event, show, anything, I even wore them when I was on tour. Might be my favorite sneaker of all time. I love the Infrared 6s — the black ones specifically ,but the white ones too. But the black ones are just so stupid; the suede, the red."