We all fell in love with the adorable brother Simmons over a decade ago when he made his appearance on the hit MTV series, Run’s House.
Photo: Giphy
As 1/8 of the Simmons household, one of Hip-Hop’s first families, it was easy for us to latch onto Diggy. That cute, raspy voice partnered with those early rap dreams and enigmatic personality won us over instantly. We tuned in every week to see what type of adventures the family would take on, laughing ourselves silly from the theme song to the always inspiring bathtub scene.
True to his family’s legacy, Diggy released several successes singles as a rapper and garnished a lot of attention as a teenage heartthrob. Now, at 21, Diggy’s ready to leave his mark on the fashion industry in an epic way. His style is only getting better with age, propelling the culture forward with statement-making looks and partnerships. With every magazine feature or brand endorsement, Simmons is no longer that adorable kid but a distinguished gentleman worthy of all praise and thirst. We’ve got a front row seat to this style glo-up and we have got to say we’re forever grateful.
Let’s talk about this D-Squared moment in Chinatown.
Photo: Tatiana-Nancy
Or, this all-black turtleneck moment that screams “simplistic style."
Photo: Flongala
Nothing’s better than Adidas at an aerial angle.
Photo: Flongala
Get into this Thom Browne suit bringing new meaning to “classic man."
Photo: Tatiana-Nancy
Pullin’ all stops in Paul Smith.
Photo: Tatiana-Nancy
A bae in Belstaff.
Photo: Tatiana-Nancy
Another swoon-worthy street style moment.
Photo: Director’s Cut Inc.
Nostalgic digs with a modern twist. Talk about getting someone who can do both.
Photo: Eric Blanks
Decked out in Dries Van Noten.
Photo: Juan Veloz
Totally killin’ the runway for Dolce and Gabbana.
Photo: Dolce and Gabbana
#ManCrushEveryday candidate in Musika Frere.
Photo: Alessandro Lo Faro
And, of course, this gem. Just for added measure.
Photo: Juan Veloz
It's safe to say we’re diggin’ Diggy.
Photo: Giphy
