"Used to rock a throwback, ballin' on the corner / now I rock a tailored suit, lookin' like an owner."

With this line from "On to the Next One" on 2009's The Blueprint 3, JAY-Z explains how his choice in clothing has changed over the years. Even those who aren't hip-hop fans know about JAY-Z's come-up – from slinging crack on the streets of Bed-Stuy, to running several multi-million dollar businesses, with a personal net worth approaching ten figures.

But unlike most folks who go from rags to riches, Hov's transformation has played out in the public eye. Fans may argue whether he's lost the lyrical touch he enjoyed during his younger years, but like it or not, few are worthy of even being mentioned with Shawn Carter when it comes to sustained commercial and critical success. You don't win 21 Grammys or get 14 different albums to Billboard's number one spot by being a flash in the pan.

"APESH*T," the video from last month's joint album Everything is Love, with his wife Beyoncé, finds JAY-Z with his most grown-man wardrobe to date, rocking pink and green designer suits and loafers with no socks.  A far cry from the jerseys, fitted hats, and sneakers that were once the signature looks of hip-hop culture. But it took the Marcy native decades of maturing to get here - not to mention help from high-powered celebrity stylist June Ambrose. 

Here are 15 videos that highlight how Jay's style has progressed right along with his bank account balance.

  • 1

    "In My Lifetime" (1995)

    In My Lifetime (single)

    Here we see Jay in his earliest video funded by his first label, Payday Records. He rocks outfits typical of the mid-'90s "Jiggy" era, including jean shorts with a wifebeater and a thin-striped, light-gray polo that looks like the shirt your uncle wore at the last family cookout. Thankfully, this era is a small footnote in Hov's fashion history. One he soon gave up for the mob-influenced stylings of the late '90s.

  • 2

    "Can't Knock the Hustle" (1996)

    Reasonable Doubt

    Reasonable Doubt stands as the most shining example of young Hov's early mafioso era —for both music and fashion. Throughout this video, he wears dark, plain suits with wide lapels and fedoras, getups that would be right at home in Goodfellas. Aside from his actual outfits, the video drips with mob imagery, from the opening drive-by "hit" to the group of men exchanging dinner jokes at an upscale restaurant with white table cloths.

  • 3

    "Can I Get A..." (1998)

    Vol. 2...Hard Knock Life

    After two albums, Jay was a rapidly-rising star in the rap world. His classic third LP cemented his status as a rap titan; to this day, it's still his best-selling album. His main outfit here is vintage hip-hop— a simple baggy jacket with a plain white tee. Look closely and you can start to see the beginnings of his plain, clean business executive style, especially in contrast with the shirtless, bandana-wearing Ja Rule.

  • 4

    "Hard Knock Life (Ghetto Anthem)" (1998)

    Vol. 2...Hard Knock Life

    For this classic Hov track that puts a hood spin on an equally-classic Broadway number, Jay again brings his own clean style to late '90s rap fashion — a long chain over a simply-designed tee with baggy jeans. It's also worth pointing out that he has one pant leg rolled up in the first scene - remember those days?

  • 5

    "Money, Cash, Hoes" (1998)

    Vol. 2...Hard Knock Life

    Everything about this video screams '90s hip-hop, from the name of the track to its featured artists—Beanie Siegel and DMX, two staples of the era. Jay's outfit is no exception, as he dons a baggy football jersey, blue jeans, and some fresh white kicks. Based on his outfit, it's easy to see why some might use this song as a way to judge him. A critique that he would brush off on "99 Problems" with the line: "Got rap critics that say he's money, cash, hoes / I'm from the hood stupid, what type of facts are those?"

     

  • 6

    "Big Pimpin" (2000)

    Vol. 3...Life and Times of S. Carter

    The one you were waiting for, and probably JAY-Z's most recognizable music video. Though he would later regret its misogynistic lyrics, this song was far and away the most successful single from his fourth album. He takes a break from his traditional rap duds to break out his best yacht-chic ensemble - white shorts and another white wifebeater. More importantly, has any other piece of pop culture done more for the bucket hat?

  • 7

    "Izzo (H.O.V.A.)" (2001)

    The Blueprint

    This video sees Jay again adopting a signature hip-hop look, the oversized plain white tee with baggy pants. Although he had started to tap into his entrepreneurial side, founding Rocawear two years before, his look here reflects how immersed he was in traditional elements of rap. He was facing multiple criminal charges and a simmering beef with Nas, which would boil over thanks to "Takeover" from the same album.

  • 8

    "Dirt Off Your Shoulder" (2004)

    The Black Album

    For The Black Album's second single, Jay continues merging his own sophisticated style with typical street swagger - note the tilted Yankee hat with a patterned dress shirt. It's no surprise that on an album that was promoted as his final record, Hov would continue to develop his own personal style of fashion. He even tells us directly in the song that he's maturing past his street days: "No chrome on the wheels / I'm a grown-up for real."

  • 9

    "Jigga What, Jigga Who" (1999)

    Vol. 2...Hard Knock Life

    With this all-black outfit featuring dark shades and a chain, Jay moves further away from his drug-dealing roots. Possibly inspired by the fashion of The Matrix and its sequels, this video also incorporates more abstract visuals. The prominent gold chain reminds us that no matter what he's wearing, Hov will always be a G.

  • 10

    "Roc Boys (And the Winner Is)..." (2007)

    American Gangster

    Now we're growing up a bit! Here Hov is donning a sharp suit with a long overcoat, perhaps his most mature outfit since the Reasonable Doubt days. It makes sense that he'd dress like a boss because he was one. By this point in his career, Jay was president of Def Jam, part owner of the then-New Jersey Nets, and had just sold the ownership rights to his clothing brand Rocawear for over $200 million.

  • 11

    "Empire State of Mind" (2009)

    The Blueprint 3

    This outfit brings an interesting "meta" element to Jay's growth. The song is all about how his early days as a hustler in the big city made him who he is; his clothing choice represents a former gangster recalling the duds he once wore. In that sense, this outfit is more street than he was actually dressing at the time, but still has an element of maturity— Hov was two months away from 40 when this video came out.

  • 12

    "On to the Next One" (2009)

    The Blueprint 3

    Again we see Jay striking his own unique balance between rapper, mature adult, and businessman, wearing a slick all-black outfit with leather gloves and jacket as he dances alongside Swizz Beatz. This video also incorporates some borderline psychedelic visuals, with floating lips, skulls, and a half-naked drummer.

  • 13

    "Otis" (2011)

    Watch the Throne

    On a collab album with Kanye West that touches on themes of racism and minority wealth, Jay wanted to remind everyone that he was still a hip-hop artist at his roots. He keeps it street simple with a touch of elegance, wearing a white tee, jeans, a gold timepiece, and of course the classic Yankee hat.

  • 14

    "Holy Grail" (2013)

    Magna Carta Holy Grail

    For the video for a song (and album) about the burdens of fame, Jay rocks all-black with a downright monstrous Cuban link chain that weighs in at over 11 pounds. His neckwear represents the pressure he feels as an artist and businessman — it's tough, but not tough enough to distract him from appreciating his life, an analogy he reinforces when he raps: "This fame hurts / but this chain worse."

  • 15

    "APESH*T" (2018)

    from Everything is Love

    Present-day HOV sees the former trap star rocking suits from labels that the skinny crack dealer from '95 probably couldn't even pronounce, let alone recognize. From Gucci loafers to Dries Van Noten suits, this song is a veritable who's-who of the high-end designer world. Oh yeah - it's also filmed in The Louvre, the most exclusive art gallery in the world. It's safe to say that Shawn Carter's transformation from street hustler to the 1% is now complete.