The Best Lil Wayne Outfits of All Time

When: 1999

Standout Piece: Cash Money Chain

“Bling Bling” was released in 1999. So it made perfect sense that all of Cash Money attended the Soul Train Awards that same year wearing outfits that focused on their jewelry. The white T-shirt, baggy denim jeans (that looked to be customized with flames on the cuff) and white Reebok Classics, a staple in the South, was the perfect canvas for their Cash Money chains, diamond bracelets and watches. While everyone else wore a hat, Wayne topped off his look with a scarf he tied around his cornrows. This is baby Wayne coming into himself as an artist and developing his own style. —Aria Hughes

When: 2005 

Standout Piece: Camo BAPE Hoodie

One of Weezy’s most highly-regarded fashion eras is the BAPE era of the late 2000s. This particular purple ensemble he rocked to the 2005 BET Awards was definitely one of the most memorable. He paired a baggy purple BAPE camo zip hoodie with an equally baggy pair of indigo jeans and black and grey patent leather Bapestas on feet. Peaking through the partially zipped hoodie is a Billionaire Boys Club T-shirt, the brainchild of Pharrell and Nigo that was another big streetwear brand of the era. Ironically, BAPE is said to have helped sparked a beef between Lil Wayne and the Clipse at the time. Following Wayne’s appearance on an equally-iconic Vibe cover from 2006 that saw him covered in cotton candy-colored BAPE pieces, Clipse released the track “Mr. Me Too” and threw some shots at him for allegedly biting their style. Clipse and Pharrell are largely credited for helping popularize BAPE in the US during the time. While the beef eventually fizzled between both rappers and Pusha T has since said the idea of BAPE starting the feud was a misunderstanding, Wayne did address the situation back in a 2006 issue of Complex while it was prominent. 

“You talking to the best. Talk to me like you’re talking to the best. I don’t see no fucking Clipse. Come on man. Weezy, man. They had to do a song with us to get hot, B. “What Happened To That Boy?” C’mon B. Don’t do that, dog," says Lil Wayne. "This is a fucking legend you’re talking to right here. 14 years, B. How many years them n****s been around? Who the fuck is Pharrell? Do you really respect him? That n**** wore BAPEs and y’all thought he was weird. I wore it and y’all thought it was hot. C’mon man. C’mon now.”

Years later, Wayne admitted that Pharrell was instrumental in him first getting interested in BAPE though telling Complex, “As far as what got me into it, I think just seeing it on Pharrell and being like, ‘What is that colorful camouflage? I need that.’”—Mike DeStefano

When: 2006 

Standout Piece: The Ice Cream T-shirt 

Now this is truly a late 2000s Lil Wayne fit. Here, Weezy is appearing on MTV’s famous TRL show rocking a crispy Ice Cream T-shirt, baggy camouflage cargos, some skate shoes, and an all-black Boston Red Sox fitted. At this point of Lil Wayne’s career he had just released Tha Carter II, which debuted at No. 2 on the Billboard 200. Lil Wayne’s success would only grow with the release of his mixtape Dedication 2 later that same year. Weezy’s fifteenth mixtape, the DJ Drama produced project is still considered to be one of the best mixtapes he has ever released. However, it is kind of ironic that Lil Wayne wore a T-shirt by Pharrell after throwing some harsh words about his style in the aforementioned Complex magazine cover story that was published later that year. —Lei Takanashi

​​​​​​When: 2006

Standout Piece: The B.B. Simon Belt

This is Lil Wayne flexing at his finest. For his appearance on MTV2’s Sucker Free, which was a weekly countdown show highlighting the top 20 hip-hop music videos of the week, he pulled up wearing a lot of stones from head to toe. This sparkling ensemble included two iced out rings, a ruby red chain, a sapphire blue chain, a bedazzled chain attached to a cross, a heavy Breitling watch frosted out on the wrist, another diamond wrist bracelet, and a classic B.B. Simon belt. Let’s also not ignore that killer T-Mobile Sidekick on the table next to Weezy, the Cadillac of cellphones at the time. Clearly, Lil Wayne was living his best life at this moment as Dedication 2 was shaping up to become one of his most critically acclaimed mixtapes of that era. For this appearance, Lil Wayne came on MTV to promote his collaborative album with Birdman titled Like Father, Like Son. That waffle thermal Ed Hardy shirt though? A classic brand from that era that was further elevated by Wayne’s contemporaries such as Juelz Santana—now that we have a Supreme x True Religion collab it’s just a matter of time for Ed Hardy’s eventual comeback. Perhaps Wayne should have worn something with some rhinestones to match the rest of his outfit. But who are we to judge? —Lei Takanashi

When: 2011

Standout Piece: “Mama Bear” Nike SB Dunk Mids

Lil Wayne certainly has never been afraid to piece together some unorthodox ensembles over the years. This is the guy we’ve seen wear a pair of snowboarding boots to attend an NBA game after all. This particular fit was also put together for one of the rapper’s many courtside appearances when he decided to pull up to American Airlines Arena in Miami to watch the 2011 Eastern Conference Finals. The top half of the fit is pretty tame, a grey Billionaire Boys Club logo hoodie and Los Angeles Lakers snapback (even though he was attending a game between the Miami Heat and Chicago Bulls). The bottom half is where things get pretty crazy. A pair of digi camo cargo shorts, white and black checkerboard socks, and “Mama Bear” Nike SB Dunk Mids complete with furry brown panels are certainly not something we’d ever suggest someone to piece together. There’s no desire whatsoever to match on display here. But somehow, the combination makes sense on Wayne. Maybe it’s because of how comfortable he looks? He owns it and you know he could care less what anyone thinks of the fit he put together. It’s so mismatched that it almost looks like it does. —Mike DeStefano

When: 2011

Standout Piece: Cheetah Jeggings

Aggressively skinny pants may have fallen out of vogue in recent years, but there was a time when people wanted their pants to be as tight as they could be without cutting off blood circulation. Case and point, Lil Wayne taking the stage in a pair of snow leopard print women’s jeggings at the 2011 VMAs. By 2011, Wayne had pretty much already cemented his legacy in hip-hop. He had decided to try and learn to play guitar. He even dropped an experimental rock album, Rebirth, in 2010. These super skinny pants were just an extension of his new rockstar image. The loud pants were actually a pair of $44 pants made by Tripp NYC. He balanced the affordability of the pants with some expensive accessories, a white Louis Vuitton belt and brown Damier print coin pouch (remember when everyone wore these?) from the brand as well. This particular photo also showcases a Weezy signature, forgoing a shirt to show off his body covered with tattoos. Wayne has famously claimed on a handful of occasions that practically his entire body is covered in ink. Younger rappers have admitted Weezy was a big influence for them deciding to get tattooed from head to toe as well. Now it’s a common visual, but back when Wayne was on top of the rap game he was one of the few individuals bold enough to get his face tatted up. His influence is undeniable. He knows it too. When speaking with Bumbu in December 2020 he simply said, “Look at me, now look at music. They all look like me. I love it.” —Mike DeStefano

When: 2012

Standout Piece: Nike Air Yeezys

In 2012, Lil Wayne launched his own label Trukfit, a line that referenced his interest in skateboarding and BAPE. But that doesn’t mean he didn’t stop wearing other brands. At this Miami Heat versus the Atlanta Hawks basketball game, Wayne, who is sitting next to actor Adrien Brody, wore a KISS hat over his Earl Sweatshirt hoodie, a cherry red G-SHOCK watch, matching GOLF WANG socks, and one of his signatures, a statement bottom. This time around he wore giraffe-print shorts. But the real flex was his Nike Air Yeezy sneakers, which hadn’t come out yet. It’s a big of a hodgepodge outfit, but it’s very Wayne. —Aria Hughes

When: 2012

Standout Piece: Trukfit T-shirt

Diddy had Sean John. Jay-Z had Rocawear. Pharrell had BBC. In January 2012, Lil Wayne added his name to the list of rappers with their own clothing brands with the launch of Trukfit. The name of the skate-inspired clothing line was said to be inspired by the trucks that would come to the New Orleans neighborhood that Wayne grew up in. They would be full of clothes that the locals would buy and the outfits would be referred to as “truck fits.” Like Diddy and Jay-Z before him, Lil Wayne would eventually strike a deal that saw Trukfit sold in Macy’s locations nationwide. It was also stocked by popular retailers like Zumiez and Karmaloop. The line of neon-colored T-shirts and boldly patterned sweats was rocked by Weezy’s most loyal supporters, but never became quite as big as some of the aforementioned brands. That didn’t stop Wayne from frequently shouting it out in tracks and wearing it pretty much everywhere at the time though. He even once rapped on “Rich As Fuck,” “I’m Tunechi, Young Tunechi, I wear TRUKFIT, fuck Gucci,” in case you had any questions about how committed he was to his creations. 

In the particular photo above, he’s seen beside skateboarding legend Stevie Williams in an orange Trukfit logo T-shirt, zebra print sweatpants, a Trukfit snapback cap, and matching pair of Nike Dunks. The two can be seen posing with a special skate deck, a collaborative project between each of their respective lines, Trukfit and DGK. —Mike DeStefano

When: 2019

Standout Piece: BAPE x Ugg Mouton Coat

By now, we’ve established that Lil Wayne isn’t afraid to take a bit of a fashion risk. One of the many was his penchant for rocking Ugg boots on stage and in music videos long before many other rappers would even consider doing so. We also are familiar with his connection to BAPE from earlier in his career. So, who better to lead a campaign for an Ugg x BAPE collab than him? The lookbook for this Spring/Summer 2019 collaboration saw the rapper front and center rocking the chestnut brown, fur-lined boots along with matching items like a Mouton coat and mittens. Each was covered with a subtle variation of BAPE’s signature camo print. 

When speaking to Complex on his involvement with the campaign back in February 2019 Wayne said, “It’s an honor ’cause BAPE is one of the clothing lines that I still remember saving my money to buy. I still remember making sure nobody else I seen in my city got my hoodie. Now, they got me involved with it?” —Mike DeStefano

When: 2023

Standout Piece: OVO x NFL Green Bay Packers Varsity Jacket

Lil Wayne may be from New Orleans, but if you know anything about him you know he is a diehard Green Bay Packers fan. The surprising fandom started in 1997 when his father came back from Super Bowl XXXI in New Orleans with tons of Packers championship memorabilia. His love for the Packers hasn't wavered since. Fittingly, he was tapped by his protege Drake’s OVO label in 2023 to model the OVO x NFL gear for the cheeseheads. In the campaign, he pairs a Packers varsity jacket covered in Packers and OVO owl patches with a white T-shirt, baggy light wash jeans, pair of buttery Timberland boots, and a black OVO beanie. You can’t get much more classic than this fit. —Mike DeStefano

When: 2023

Standout Piece: custom OVO owl chain

Lil Wayne is nothing short of a hip-hop icon. In 2023, his contributions were recognized by The Black Music Collective. Here, he can be seen accepting his Recording Academy Global Impact Award during the Recording Academy Honors. However, you should never expect Weezy to show up in a suit and tie to the awards ceremony. He’s always going to stay true to his unique style. In recent years, that means plenty of baggy garments from Balenciaga. For the special acceptance, he went with a black Campaign logo crewneck, all-over print pants black viscose pajama pants, and bright pink Bouncer sneakers all from the Spanish luxury brand. The gold OVO owl pendant around his neck made for the perfect accessory. —Mike DeStefano

When: 2023

Standout Piece: Loewe x Howl's Moving Castle Trench Coat

Like we’ve said before, Lil Wayne never sacrifices his unique fashion sense for the sake of a dress code. The 65th Grammy Awards were no different. He didn’t just wear a white button-up. He wore it untucked and oversized. He didn’t just wear some tailored black trousers. He opted to keep them baggy, how he typically wears them. The finishing touches were a tartan trench coat and denim sneakers from Loewe that were part of its capsule collection with Studio Ghibli inspired by the anime film Howl’s Moving Castle. Each piece was adorned with colorful jewels to nod to the jewels found in Howl’s room in the movie. Is Weezy a big Studio Ghibli fan? Not sure. Nonetheless, he pulled these pieces off effortlessly. Maybe they peaked his interest enough to check it out. —Mike DeStefano