The Best ASAP Rocky Outfits

When: 2019

One of the reasons ASAP Rocky is held in such regard for style is his ability to seamlessly transition between streetwear and runway-ready looks. This particular night, Rocky opted for the latter to attend the 2019 Pre-Grammy Gala. He showed up to the Beverly Hilton Hotel dressed head-to-toe in an oversized pink suit ripped straight off the runway of Jonathan Anderson’s inaugural Loewe show at Fall/Winter 2019 Paris Fashion Week, Men’s. Rocky put his own twist on the look by tucking in only one side of his white shirt.

When: 2019

While travelling across the country for his “Injured Generation” tour earlier this year, Rocky made sure he stayed fitted for each show. This particular outfit worn during the tour’s stop in Duluth, Georgia is easily one of the most memorable. Rocky hit the stage in a matching Prada jacket and pants covered in flames. He completed the Bam Bam Bigelow-esque ensemble with a classic pair of “Bred” Air Jordan 1s on feet and a test dummy-inspired ski mask一a piece he frequently wore on stage during the tour.

When: 2019

Since the untimely passing of ASAP Yams in 2015, Rocky has celebrated the legacy of Yamborghini every year with a Yams Day concert in New York City that’s featured everyone from Flatbush Zombies to Soulja Boy. For the 2019 show at the Barclays Center in Brooklyn, Rocky came through in a streetwear-inspired look that included a vibrant pair of Needles track pants, a yellow bandana repurposed as a babushka, and ski mask that nodded to his most recent album "Testing." The highlight was a VLONE T-shirt emblazoned with a graphic of Yams as legendary pro wrestler Stone Cold Steve Austin.

When: 2018

“He’s a trendsetter, you ain’t even peep that,” Rocky says on his song “Multiply,” and he’s right. Rocky’s been responsible for amplifying a handful of trends and brands over the years ranging from Hood By Air to Needles track pants. While his most recent accessory of choice, the babushka, might not have the same pick up, it represents Rocky’s individual style and his ability to make anything his own. Typically worn by Russian and Polish grandmothers, Pretty Flacko made the head scarf a wardrobe staple in 2018. A song even surfaced that was named after the traditional head piece. One of his more notable fits featuring the babushka was in 2018 at The Los Angeles County Museum of Art and Film Gala when he showed up in a classic navy blue suit, floral babushka, a colorful Gucci silk robe, and fur-lined Gucci mules.  

When: 2018

Sometimes it doesn’t take much to put together a clean outfit. Case in point, Rocky’s garb for Rihanna’s fourth annual Diamond Ball. He showed up to the star-studded event in a custom all-black Berluti suit with satin detailing on the lapel and a tuxedo stripe down each pant leg. Keeping it cozy, he laced up a pair of white Dior sneakers instead of some hard bottoms to make the look a little more casual.

When: 2018

Kim Jones’ debut runway show as the artistic director of Dior menswear was a big moment for fashion last year that furthered the melding of streetwear and luxury. Rocky, a former face of the brand, dressed for the occasion in a slouchy grey Dior suit paired with a mesh undershirt covered in the fashion house’s signature monogram print. White and silver Dior runners completed his front row look.

When: 2018

When Rocky rolled up to the Dries Van Noten show at Paris Fashion Week Men’s Spring/Summer 2019, he made sure he was going to be noticed. The 30-year-old came dressed in a matching top and bottom from Loewe’s Spring 2019 men’s collection crafted by piecing together colorful fabrics inspired by traditional bandanas. He completed the look with a black and white Vans Old Skool—a go-to option for the Harlem-born rapper.

When: 2018

Lord Flacko hit the stage for the 2018 Parklife Festival in England showing off his eye for mixing streetwear pieces with luxury items. The leader of the ASAP Mob was rocking an Air Jordan T-shirt donning "His Airness" across the front. The design would later be used by Chris Gibbs as a part of the Union x Air Jordan collaboration that released in November 2018. Draped over the that was a striped, oversized cardigan from Raf Simons’ Fall/Winter 2017 collection.

When: 2018

Rocky’s love for Raf Simons, who used to be the creative director for Calvin Klein, is well documented. That’s why seeing him roll up to the Calvin Klein show during New York Fashion Week last year in a head-to-toe outfit from Simons’ 205W39NYC collection isn’t not shocking. The rapper paired an oversized striped sweater with burgundy trousers. The highlight of this fit is the bulky navy blue and olive green winter coat.

When: 2017

Rocky seems to have an affinity for vintage Air Jordan pieces. Not only does he frequently wear original Air Jordan 1s from 1985, he also has some other noteworthy apparel pieces in his closet. Here, Rocky can be seen in a black Jordan baseball jersey from 1992. The top is paired with black denim and gold jewelry on his neck and wrist.

When: 2017

A lot of people like to keep it cozy in sweatpants and a hoodie when they hit the airport, but when you’re a fashion  icon like ASAP Rocky, you always keep it a bit more stylish than most. Rocky stepped out of LAX on this day in a white hoodie layered with a black blazer, baggy grey trousers, and a pair of the highly-coveted and ultra expensive “Chicago” Off-White x Air Jordan 1s designed by Virgil Abloh. An Alyx studio bag slung over his shoulder is the perfect carry-on.

When: 2017

Gucci’s resurgence through playful and bold embroidery has been seen on many celebrities, but this Rocky fit has to be one of the best. In a floral embroidered hoodie. embroidered velour overcoat, track pants, loafers and shades—all Gucci, of course—Flacko looks like he just stepped off the runway. Most people can’t pull off this many graphic-heavy pieces at once, but he is certainly someone who can.

When: 2017

Nothing is better than a perfectly tailored suit. Rocky made this evident with his amFAR Gala attire in Cannes this past May, when he rocked a simple black Gucci two-piece suit and leather loafers. The rings and blinged-out bracelet added some subtle braggadocio to the otherwise relaxed ensemble.

When: 2017

Sometimes it isn’t what you wear, but how you wear it. Case in point? This fit from the Balmain After-Party at Paris Fashion Week Fall/Winter 2017. If you can rock a Miller Lite hockey jersey at Balmain’s after-party and still look like you belong there, you deserve some credit.

When: 2017

What better way to flaunt your boss status than to rock Vito Corleone on your chest? That’s exactly what Rocky did when he busted out this rare Bathing Ape x Godfather collab from 2008 while performing at this past year’s Summer Jam concert. He kept the rest of the outfit simple, with a pair of white pants and classic Vans Old Skools.

When: 2015

When ASAP Rocky performed alongside Twenty One Pilots at the 2015 VMAs, Gosha Rubchinskiy was far from the brand it is today. Rocky can certainly be credited for shedding some light on the Russian designer when he rocked an all-black head-to-toe Gosha fit onstage. The flag logo hoodie he wore become a hot commodity shortly after the award show aired.

When: 2015

Rocky’s Grammy Awards fit from 2015 is another example of his love for Gucci’s embroidered garments. Here, he paired embroidered denim with a floral knit cardigan. However, the real standout piece here is the navy blue Goyard messenger bag. It was also a feel-good moment seeing him bring ASAP Yams’ mother to the event as his plus one after her son’s untimely passing just a month earlier.

When: 2013

This one is a bit of a throwback to when Rocky was still rocking streetwear pretty heavily. He keeps it fairly simple, opting for a pair of black skinny jeans and classic white-on-white Air Force One mids (a staple for him at the time). The highlight of this outfit is the white, black, and teal Supreme football jersey from the brand’s Fall/Winter 2013 collection.

When: 2017

To attend Raf Simons’ first show as Calvin Klein’s Chief Creative Director, Rocky decided to pull out a quintessential cozy-boy fit. He’s rocked a vintage orange fleece Calvin Klein zip-up jacket covered by a red Balenciaga bubble coat, and a red Balenciaga fanny pack to match. He keeps the red theme with a pair of red pants, and finishes it off with a pair of unreleased VLONE x Nike Air Force One Highs on his feet. Too cozy.

When: 2013

A simple shirt change can be all you need. Here, Rocky sports the same black skinny jeans and white Air Force 1 mids from the Reading Music Festival, but switches up his T-shirt. The reason this is such a big deal is that the shirt happens to be one of the most coveted Supreme collaborations of all time, the Dipset photo T-shirt, featuring fellow Harlem rap legends Juelz Santana and Jim Jones.

When: 2017

Although Rocky is known to rock some outlandish stuff only a select few can pull off, this has got to be an outfit that literally only he can make not look absolutely horrendous. Appearing alongside Playboi Carti in the official video for the rap rookie’s hit “Magnolia,” Rocky chose to sport an VLONE long sleeve T-shirt  inside-out (on purpose), Dickies work pants with reflective detailing, and a pair of Shattered Backboard Air Jordan 1’s. Those pants weren’t some Vetements collaboration with Dickies, though. They are available on Dickies’ website for under $40 here.

When: 2017

There’s few flex moves greater than stunting in something that is one of one. This past February, while attending the Raf Simons Runway Show at New York Fashion Week: Men's, Rocky donned a custom striped mink coat designed by none other than himself. To complete the outfit, he rocked a Gosha Rubchinskiy x Fila T-shirt underneath, Prada trousers, and Gosha’s Fila collaboration sneakers on his feet. The Gosha x Retrosuperfuture shades and Fendi coin pouch are nice finishing touches.

When: 2016

Perhaps inspired by the words of fellow fashion god Kanye West— “You see this coat?!”—Rocky rolled up to Ye’s Yeezy Season 3 Fashion Show at Madison Square Garden rocking this black fur trench. In case that wasn’t enough of a statement piece, he was also rocking the black Dorothy T-shirt from Supreme’s Spring/Summer 2013 collection, and a burgundy Gosha Rubchinskiy beanie as well.

When: 2017

Rocky showed up to the Christian Dior Haute Couture Spring/Summer 2017 Show decked out in pieces from Dior Homme’s Fall/Winter 2017 Collection. Rocking a brown fur bomber jacket over a “They Should Just Let Us Rave” turtleneck and a pair of black trousers with suspenders, Rocky looked like he should have been strutting down the runway himself. Once again, Rocky added his own personal streetwear touch by rocking his pair of VLONE x Nike Air Force Ones.

When: 2016

Sometimes less is more. During his performance at the Reading Music Festival in 2016, Rocky kept it clean and simple by rocking a pair of black skinny jeans with a white graphic T-shirt from Public Housing Skate Team. But the standout piece from this fit were his OG pair of “Chicago” Air Jordan 1s from 1985.

When: 2017

ASAP Rocky loves Raf Simons—it’s no secret. He even has a track named after the iconic Belgian designer. So, it should have been no surprise when Rocky arrived at the 2017 Met Gala dressed in head-to-toe black denim from Simons’ debut 205W39NYC collection for Calvin Klein. Although it’s not the typical suit usually seen being worn at the event, it was a perfect way for Rocky to showcase a balance between casual and formal wear.