By Helena Madonna

In 1995, the award for Best New Rap Group was announced at the Source Awards. To an agitated crowd harmonizing in a chorus of boos, Atlanta-based duo OutKast, took to the stage to accept their very first award.

To look at the mountain of success, influence and transformative impact Andre 3000 and Big Boi have had, not only on the rap landscape but on pop culture as a whole, it's hard to fathom that there's even a slight possibility they once faced a booing crowd.

In the early 90s however, the rap climate was heavily doused in the east-west coast rivalry and with OutKast emerging onto the scene from the south, they were considered the underdogs

Known under many names, one being 'the poet', Andre 3000 spit six famous words during his acceptance speech "The South got something to say". From that day forward, the rap duo continued reminding us how those words ring true.

Excelling in the balance of navigating between discussing systemic issues like racism and poverty while simultaneously relishing in and celebrating Black culture, proves why OutKast connect to broad audiences and across generations.

The duo emerged with a fierce, fearless approach to most parts of their early career, one being their rejection of 90's rap attire. Doing so by wearing wigs, furs, kilts and pastel-coloured suits, that challenged masculinity in hip-hop.

These days, you'll find an aesthetically more relaxed Andre 3K, usually seen sporting a beanie, dungarees and his humble flute (but more on that below). Regardless of what they're wearing, it's safe to say that there's never a dull style moment and us fans are always watching.

With such an eclectic mix of eccentric, iconic looks it's hard to compile them to highlight a few but we've made a calculated attempt. So whether you know them as the Two Broke Boyz (In a Cadillac) or as the Scooby snack-eating duo from A Land of a Million Drums, please enjoy the many faces, phases and eras of OutKast.