Happy Birthday Hov: A Look Back at Some of Jay-Z's Most Memorable Outfits

Image via Getty/Theo Wargo

Year: 1989

Years before Jay-Z would drop his first single “In My Lifetime,” he was dressing like the rap star he was destined to become. Here’s a young Jay-Z wearing a simple striped T-shirt with a snapback. But of course, no one can ignore the giant Gucci link chain he’s rocking. Hov fans know that ‘89 was an pivotal year in Jay-Z’s career. It was when his mentor Jaz O, who’s to the left of Jay Z in this photo, got briefly signed to EMI and introduced his fellow Marcy Projects native to the music industry. Trust that Jay-Z's jewelry game was hitting crazy as a youngin. Who could even imagine an 18-year-old kid walking into a room with jewelry like this. —Lei Takanashi

Year: 2001

Back in the late '90s and early 2000s, a closet wasn't complete unless it had at least a couple of "way too big" throwback jerseys in it, and few collection's rivaled Hov's. A throwback Julius Erving Sixers jersey paired with a white Roc Nation T-shirt tied around his head, a Latrell Spreewell Knicks jersey standing next to Michael Jackson on the Summer Jam stage in 2001, or a Jets jersey with the green fitted to match were just some of the fits in his repertoire at the time. But this particular fit worn by Jay-Z to perform "Izzo" at the 2001 MTV VMAs is among the best. He took the stage outside of the Metroplitan Opera House in New York City rocking a white Michael Jordan Bulls jersey, baggy denim shorts, and a pair of "Fire Red" Air Jordan Vs. Almost two decades later, the jersey choice was a nice bit of foreshadowing. Both men are widely considered the GOATs of their respective crafts. —Mike DeStefano

Year: 2001

We can’t not include du-rag Hov. It’s not even that this outfit is that great, it’s just indicative of a specific time when Jay-Z wore a closely cropped caesar instead of Basquiat-esque dreads, and he preserved his waves with a du-rag that usually matched his outfit. But it wasn’t merely an accessory. Jay-Z understood the symbolism. He understood the du-rag was a piece of Black culture that not everyone deemed appropriate for certain settings. He raps about the scenario in “So Ghetto,” when a young lady says, "Jigga-Man you rich, take the du-rag off" and he drops her off back at the club. He responds: “Thug n**** 'til the end, tell a friend bitch. Won't change for no paper plus I been rich.” —Aria Hughes

Year: 2002

Personally, if you’re going to rock an all blue fit, a Smurfs T-shirt would have been more fitting. However, Jay-Z still murdered this look with a royal blue velour tracksuit top while sporting a royal blue Puma headband. The iced out Rocawear chain is a nice subtle flex, too. In December of that year, Jay-Z signed a historic deal with Reebok that lasted until 2007. The collaboration solidifed Jay-Z's influence on fashion in the 2000s. Reebok experienced an 11 percent jump in footwear sales after signing Jay and 50 Cent in 2003.— Lei Takanashi

Year: 2003

When “Change Clothes” came out, Jay-Z was approaching his mid-30s, signing deals with large corporations, and wanting to mature aesthetically. His solution was a button-up shirt, that he wore oversized and untucked and in a color scheme or pattern that matched his sneakers or hat. Here he’s wearing a striped version coming in different shades of maroon with a New York Knicks fitted, baggy jeans, and his staple, white AF1s. — Aria Hughes

Year: 2003

Once upon a time, when MTV was still relevant, they attempted to launch a series of “MC Battles” in Times Square. According to a Billboard article on the first battle, after 32 MCs were chosen from a pool of 1,000, they would battle each other on live TV to win $25,000 and a record deal with whatever label sponsored the event. The second battle was sponsored by Roc-A-Fella records and Jay-Z showed up to give a live performance in the middle of Times Square. Hov came through wearing what is likely one of the flyest pieces of Rocawear x State Property merch that we’ve ever seen. A corduroy utility jacket that could rival a piece designed by Junya Watanabe—just look at how crazy the zippers on this jacket are. Oh yeah, a young Kanye West is also in the photo. But compared to Ye, Jay-Z’s fit is unmatched.—Lei Takanashi

Year: 2004

Although this tour was short lived and riddled with drama — R.Kelly left the show after claiming two men  waved guns at him during the Madison Square Garden date — it did produce this fit, which is quintessential Jay-Z in the early half of the 2000s. Baggy Evisu jeans? Check. S. Carter sneakers? Check. Something designer? Check. This time around it was a monogrammed Gucci jacket, which we are certain is custom, that matched the green and red Gucci stripe on the jeans. This was when matching/coordination was the ultimate flex. — Aria Hughes

Year: 2009

Jay-Z certainly wasn't the first person to piece together an all black outfit. But thanks to his "All Black Everything" era back in 2009, he's likely to be the first person that comes to mind for a lot of people when it comes to the stealthy wardrobe choice. Not many of the legend's fits strayed away from the above back then. Black sunglasses, black T-shirt, black leather jacket, black denim, and a Jesus piece dangling from his neck for good measure. If you needed proof of how serious he took the look, look no further then some of his lyrics on The Blueprint 3—"Black cards, black cars, all black everything," on "Run This Down" or "I might wear black for a year straight," on "D.O.A." The man was committed. —Mike DeStefano

Year: 2012

As Jay-Z aged, his wardrobe matured with him. By 2012, he had left the baggy jerseys and Rocawear sweatsuits in the closet in favor of a much more dapper look. A crisp tailored suit was now a go-to choice for the then-43-year-old rapper. He'd even rock the occasional bow tie to up the formal look another notch. As is often the case, his music at the time aligned with his current style too. He spit a guest verse on Justin Timberlake's "Suit and Tie" and expressed his love for legendary menswear designer Tom Ford by titling the third track on "Magna Carta Holy Grail" after him. Like he said, "Tom Ford tuxedos for no reason."—Mike DeStefano