Although OutKast’s stylistic beginnings were typical in relation to the aesthetics of ’90’s rappers—Atlanta Braves jerseys and baseball caps indicative of their hometown paired with Nikes and loose-fitting pants in their video for “Player’s Ball”—the duo also showed flashes of their eccentric tastes to come: from André 3000’s furry Kangols to Big Boi’s coordinated chessboard flat cap and tracksuit in the video for “Southernplayalisticadillacmuzik.” And, while Big Boi’s baggy Adidas track pants in the aforementioned videos would be spot on trend today, they were nothing special back in 1994.

With the ’96 release of OutKast’s sophomore album, ATLiens, André 3000 seemed to transform into the superhero depicted in the album’s cover art. With his head wrapped meticulously in an array of turbans to fit the Egyptian theme represented in the videos for “ATLiens,” “Elevators
(Me & You)” and “Jazzy Belles,” 3 Stacks debuted a range of on-theme looks, from four-pocket safari shirts to elaborately embroidered dashikis. Meanwhile, Big Boi kept it “cooler than a polar bear’s toenails” in unbranded football shirts and a Canadian tuxedo.

On the track “West Savannah” off OutKast’s third album, Aquemini, Big Boi raps, “Been wearing furry Kangols, so that shit is old,” announcing a new era for the duo’s style. While Big Boi’s outfits became subtly trendsetting, André 3000’s became full-blown flamboyant a la ’70s and early ’80s hip-hop legends, such as Grandmaster Flash & the Furious Five, when rappers still dressed like rock stars. In “Rosa Parks,” 3 Stacks embraced football pads as fashion five years before Bernhard Willhelm would debut his AW04-05 “American Football” collection and more than a decade before big shoulders would come back in style. In “Skew It on the Bar-B,” André 3000 may look like a lost member of the Thundercats with his white wig paired with white fur shorts and white fur cuffs, but he also rocks a pair of snowboarding boots way before Pharrell tried to make them a trend.

And, while André 3000 was clearly the more showy of the duo during this period, Big Boi was just as influential. From being one of, if not the, [first hip-hop stars to co-sign Mitchell & Ness by wearing a Dale Murphy Atlanta Braves jersey] in “Skew It on the Bar-B” vido to rocking pairs of Nike Air Max Plus Tns in multiple videos, he was most certainly ahead of his time. Never one to be outshone, Big Boi also showed some flare, wearing a black crewneck with cuff flame details in “Da Art of Storytellin’” decades well before Vetements x Thrasher was a thing, and even showing an affinity for clout goggle-esque sunglasses and fur coats.

In 2000, OutKast released Stankonia, their most sonically adventurous project yet, and the duo followed with similarly experimental styling and visuals. Following his the ATLiens-era stint as a superhero, for OutKast’s fourth studio album Dre assumed the role of reincarnated rock legend Jim Hendrix, a decade and a half before he would play the icon on the silver screen. While André 3000 went full-on-Hendrix for “B.O.B,” with an assortment of colorful bell-bottom trousers and sashes, Big Boi continued to rep Mitchell & Ness, while also showing a fondness for sweat suits. For “So Fresh, So Clean,” André 3000 continued his Hendrix impersonation and Big Boi made silk polka dot pajamas look like fly daywear without a Vogue cosign. Shit got wild when the pair decided that King Henry VIII was an unsung fashion hero for their church scene in the same video. While 3 Stacks got even weirder in “The Whole World,” with a diamond-patterned rainbow cape, and politically dubious courtesy of a confederate flag belt buckle in “Ms. Jackson,”, Big Boi made was the trendsetter, sporing an iconic look during an appearance at the 2001 MTV Video Music Awards.

Although it seems like every and any hip-hop artist these days claims to be a sneakerhead, going “Sneaker Shopping” with Joe La Puma and posting Instagram shots of custom built sneaker closets and limited edition kicks, throw back to the early 2000s and the modern sneaker era of Quickstrike/Tier Zero releases had barely gotten off the ground. Enter Big Boi’s outfit for the 2001 MTV Video Music Awards. While André 3000 was literally dressed like a carrot, Sir Lucious Left Foot had on a fresh pair of Concept Japan Nike Air Force 1 “Linens” and a pair of furry pink shorts that would make the pink god himself, Cam’ron, jealous. Sure, rappers wore white on whites—“Uptowns”—back then, as well as various popular Nike, Adidas, Puma and Reebok silhouettes since the advent of hip-hop, it was rare to see a mainstream artist flex a pair of truly rare Nikes, let alone a Japan-only release, at a major awards show. To be clear, Big Boi’s Linens were no fluke—he also rocked a pair of just as rare patent leather Nike Air Force 1 “Taiwan’s” for a 2002 appearance on The Tonight Show with Jay Leno.

Big Boi’s vicious sneaker game was just a taste of OutKast’s flair for future trends. In 2001, as a promo for Levi’s Engineered Jeans, OutKast and Levi’s worked on an until recently unreleased UK-only sampler album accompanied by a series of photos shot by [Jamil GS]. Decked out in matching raw denim fits sublty tuned to their individual style, André 3000 and Big Boi were simultaneously on trend and lightyears ahead of their time. Although the denim-on-denim look was common for rappers of the era, the raw/selvedge denim craze wouldn’t hit the U.S. until the mid-2000’s. While Big Boi’s outfit would feel at home in [A Bathing Ape’s 2008 lookbook featuring Kanye] minus the Levi’s branding, Dré’s ensemble made denim look avant-garde.

OutKast’s pulse for the future state of fashion is arguably most apparent in the videos that accompanied their 2003 split album, Speakerboxxx/The Love Below. Independently, and together, André 3000 and Big Boi highlight the ’50s and ’60s Americana style that helped spur the raw denim craze of the mid-to-late 2000’s and the ’70s silhouettes and patterns that have recently reappeared on runways. The video for the duo’s single “Roses” pits Andre 3000’s The Love Below crew against Big Boi’s Speakerboxxx gang in a retelling of the musical West Side Story, inspired by teens in the ‘60s. While 3 Stacks and his squad wear Levi’s raw selvedge denim, high top black and white Chuck Taylors, ties/bowties and custom embroidered red cardigans, Big Boi and his menacing henchmen stand tough in black and red letterman jackets. Incredibly, every single aforementioned garment and accessory emerged as fashionable throughout the decade.

Despite his appearance in “Roses,” Big Boi’s real contribution to the next fifteen years of fashion were his outfits in the “The Way You Move,” video. Sir Lucious Left Foot steps out stuntin in pair of flared suits (including a ’70’s plaid leisure suit) before transforming into a precurosr to Kendrick Lamar’s onstage alter-ego, Kung Fu Kenny. Draped in a blue and white striped karate gi from the now defunct Outkast Clothing, his take on martial arts style set the precdent for artists moving forward. It would only take another twelve years for traditional Japanese garments to become a major influence on American (and international) fashion, and a couple more for ‘70s patterns and silhouettes to come back in style.

Although the video for “Hey Ya!,” arguably OutKast’s biggest hit from Speakerboxxx/The Love Below, features André 3000 in a spectrum of outfits, the track is, from a style standpoint, the least influential from the album. While one version of 3 Stacks shows off a tight tucked-in black turtleneck with racing green tuxedo striped trousers and another version wears a beret—cue AW16 trends—real life André 3000 put in just as much, if not more, work with his personal wardrobe. During this period, he experimented with an array of high-risk outfits that might as well have been a crystal ball for future trends. From the [baggy, perfectly hemmed pleated trousers] and red beret he wore at MTV’s Video Music Awards to the buttery brown bomber jacket he wore to that rocked at the Sundance Film Festival, he consistently proved how style-conscious he was.

Four years before the sartorially inclined found an online space to argue over the ideal width of a lapel with the #menswear movement, André 3000 and Big Boi got all dressed up for their 2006 HBO film and soundtrack, Idlewild. Both the film and the soundtrack are largely considered OutKast’s most mediocre work, but the ’30s prohibition style that permeates the film predicted what became the dominant menswear trend during the first half of the next decade—men once again caring about tailoring. Tweeds, pinstripes, pocket squares, collar bars, vests and intricately patterned ties are all abundant in the film, and subsequently became even more abundant on the bodies of stylish men shortly thereafter.

The vintage American style of Idelwild carried over into André 3000’s personal closet as well, from the faded denim chore coat and red neckerchief he wore for the 2006 VH1 hip-hop Honors Awards Show to the dark denim, Chuck Taylors, and yellow varsity jacket with metal clasps he wore on TRL. While 3 Stacks also rocked a pair of faded black multi-pocket cargos reminiscent of Greg Lauren and TAKAHIROMIYASHITA The Soloist., Big Boi had his own prognosticative fits, such as the safari blazer and floral bucket hat he wore for the 2006 BET Awards.

Although OutKast has not released a project since Idlewild, Big Boi and André 3000 have stayed active in their own ways. Sir Lucious Left Foot has dropped three solo albums and one collaborative album with Phantogram under the moniker, “Big Grams.” 3 Stacks has made a series of stunning guest appearances and starred in films, including the Jimmy Hendrix Biopic, Jimi: All is by My Side. While both artists have continued to demonstrate a keen and, at times, outlandish sense of style, neither Big Boi nor André 3000’s sartorial choices have been as prophetic as they once were. Both artists stayed suited in their first individual video appearances post-Idlewild—the former in 2010‘s “Shutterbug” and the latter as a feature in John Legend’s 2009 video for “Green Light”—however have leaned toward designer streetwear as the years have progressed.

As Big Boi continues to demonstrate his sneakerhead credentials, with occasional designer flexes to boot (such as the fur collared rider’s jacket he sported with a pair of Fear of God Military High Top Sneakers in this year’s video for “Kill Jill”), André 3000 has shown an affinity for military-inspired outerwear, overalls and low-top sneakers. Earlier this year, 3 Stacks was named creative director for Swedish brand Tretorn, but arguably his most memorable recent contribution to fashion is the black flight suits he wore for OutKast’s 2014 reunion tour. Featuring politically-bent messages—“have you stopped growing?” and “across cultures, darker people suffer most. why?”—along with a giant price tag featuring a dollar sign on one side and “Sold” on the other, the suits served as commentary on André 3000’s ambivalence towards the tour. Eventually, the forty-seven flight suits were shown at a mixed-media exhibit dubbed “i feel ya: SCAD + Andre 3000 Benjamin,”, as part of Art Basel Miami.

While there are numerous explanations for OutKast’s diminished status as trendsetters over the past ten years—the explosion of fashion in hip-hop, the stylistic fragmentation of the menswear industry, Big Boi and André 3000’s sporadic public appearances as solo artists—their overall impact on the visual and sonic aesthetics of hip-hop and fashion since their 1991 debut is undeniable. Much of what we see on stage, in music videos and on the red carpet today is indebted to the dynamic duo from the A. Whether or not the much hyped reunion album, or an André 3000 solo album for that matter, ever surface, the duo's legacy is unquestionable.