The Most Stylish R&B Singers of the '90s

Teddy Riley had his hand in some of the early '90s most popular R&B groups: Guy, Wreckx-n-Effect, and of course, Blackstreet. The latter quartet proved to be Riley's most successful, and also most stylish. The group fit the bill for what a '90s R&B should be: a harmonizing group of dudes who weren't afraid to rock fly and lavish gear. The group could be found in an array of overalls, oversized outerwear, and even the rugged uniform of leather jackets and boots. Blackstreet may have been your favorite rapper's go-to group if they needed a fresh hook on a smooth track, but we're sure dudes picked up a few style tips from this group who played the back.

R. Kelly should have named his Space Jam theme, "I Believe I'm Fly." The much-maligned singer was super fresh in the '90s, and even rocked an infant size pair of Air Jordan 13s around his neck during a performance. But don't think Kelly's style was strictly for the hypebeasts—in fact, the singer had a vibrant collection of tailored clothing to fit the decade's appetite for flash. Kelly's desire for standout gear didn't stop there, as he would rock leather vests, a mainstay in the genre's sex-filled anthems of the time period.

It might seem awkward to put D'Angelo on a "most stylish" list since he is best known for not wearing anything. But when the singer decided to dress, especially in the '90s, he had a great sense of style. Besides a set of abs that got your girl hot andbothered, the other iconic image of D'Angelo is the cover of his debut album, Brown Sugar, decked out in a leather bomber jacket.

Shai knew how to switch things up. The D.C.-based quartet would fit in well in today's style blogosphere. No, really, they would. The guys had suits, workwear, and even early streetwear that they could pull out. It even looks like they might have rocked a Barbour jacket from time to time. The group's collective style is the equivalent to the #menswear nerd who can rock sneakers and a blazer (but not at the same damn time).

The lasting image of Jon B. is of a perfectly trimmed haircut and beard, but the singer and 2Pac collaborator also had an on-point tailored game, too. In his "Are U Still Down?" video, the singer rocks a suit, suspenders, and hat—along with a gratuitous tie clip and silk robe. Jon B. was able to switch up his style as well—in his "They Don't Know" video, the singer is spotted in a bubble jacket with fleece jacket underneath, one of the hip-hop styles of the day. Although Jon B.'s music was definitively R&B, his chameleon-like style shows that singers could be influenced by other genres.

It's debatable whether Sisqó was actually stylish, but the platinum-locked frontman of Dru Hill had the youth of the day craving a frosted dome. Sometimes, it's not how well dressed you are, but how much influence you have that creates an impenetrable aura. Also, it doesn't hurt to have less stylish dudes placed around you. It made it easy for Sisqó to stunt the hardest out of his group. Plus, he convinced a legion of women to start rocking thongs. Thank you—we think.

It's hard not to have style or bravado when you're signed by one of Southern rap's founding fathers, Uncle Luke. In fact, R&B group H-Town's gear might have been the real reason they were "Knockin' Boots." Like many other acts of the day, the group was able to switch up looks. From styles that will run your parents off the block to matching Canadian tuxedos, H-Town proved that the average R&B group didn't have to put on their Sunday best to get the ladies screaming. They could do it their way.

Silk were a bunch of Gs. The R&B group reportedly forced Silkk the Shocker to add an extra "K" to his name. Besides stunting on a member of No Limit Records, Silk could dress pretty smooth. Although the '90s was the decade of matching gear for R&B ensembles, Silk managed to rock similar-enough gear to look put together, but not too matchy matchy. If you're not a fan of sporting the exact same thing as your friends, Silk was a shining example of how subtle differences can go a long way.

Montell Jordan's South Central L.A. swagger easily translated over to hip-hop-friendly R&B records, as the singer would collaborate with Slick Rick, Master P, and Silkk the Shocker. But Jordan is also recognized for his dapper style. Not afraid to light up a cigar, Jordan would don suits befitting of the mid '90s, as well as snakeskin jackets and even a hip-hop-approved look from time to time. When he exclaimed, "This is how we do it," Jordan might have been sartorially speaking, too.

It's not fair, little kids can be more stylish than adults—sometimes. What's great about pint-sized R&B group Another Bad Creation is that they actually rocked all the gear we remember was great in the '90s: Nike sneakers, Starter apparel, snapbacks, work boots, and workwear, all in classic '90s style—oversized and bright. While we all know your mom was dressing you in Bugle Boy and knockoff sneakers, this is how you'd like to remember your style from two decades ago.

Admittedly, a lot of kids back in the ‘90s had no clue what Next’s "Too Close" was about—until they heard the song 10 years later. However, what they did know: the R&B group was one of the best-dressed acts of the era. It only takes one view of the aforementioned video to remember how stylish these guys were. From coordinated all-black kits to bright outerwear and even a Stephon Marbury Minnesota Timberwolves jersey, Next’s style was way cooler than shiny suits. Way cooler.

Soul for Real may have been an R&B group, but under the influence of mentor Heavy D (R.I.P.), the quartet picked up a knack for hip-hop style. Group members (and brothers) Jason, Brian, Andre, and Christopher Dalyrimple dressed in R&B fashion with matching outfits, but rocked baggy pants, custom leather jackets, and even a Kangol hat or backwards cap. Still, despite preferring street-inspired looks, the group knew when it was time to get a little more dapper, rocking black leather jackets and a suit or two.

IMx, or better known as Immature in the ‘90s, not only transitioned from boyhood singers to a legitimate R&B act, but also through a handful of styles. Headed by Marques Houston, the group, which also consisted of members Jerome “Romeo” Jones and Kelton "LDB" Kessee, rocked ultra-baggy gear, matching outfits, and one of the hardest pieces for guys to legitimately pull off: the vest. Group member Romeo even sported an eyepatch through most of his career—allegedly caused by Brandy hitting him in the eye. Sometimes you have to suffer for style. As the boys got older, their style seemed to wane. Still, the group was able to successfully replace their high-top box fades and hip-hop-like clothes for shiny suits and still look cool.

What's not to love about matching purple, double-breasted blazers with Nike Air Classic BWs? Seriously. What Texas-based R&B group Hi-Five lacked in career sustainability, it sure made up for in pure swagger. The group's suits might not have been the best-fitting options, but the loud ties, individual flair, and mixed-in sports gear balanced out a plethora of faux pas. Have you ever seen someone so irrationally dressed that it somehow looks dope? That's these guys.

Formed from the remnants of New Edition, Boston natives Bell Biv Devoe might be forever known for their 1990 hit single, "Poison." But the group didn't only mix upbeat rhythms over R&B vocals, the members also appropriated hip-hop fashion—matching varsity jackets, sports apparel, high-top box fades, and even the most dandy of menswear options.

Boyz II Men might be remembered as possibly the best male harmonizing group of the '90s, but the Philadelphia natives were also known for their signature look: the flyest of matching outfits. Group members Shawn Stockman, Wanya Morris, Nathan Morris, and Michael McCary had no issue with rocking the same gear, frequently mixing snapbacks with tailored looks that were accented with bow ties. Plus, the guys knew how to keep it simple and rock crisp leather jackets. We don't recommend that you and your friends walk around in coordinated gear, but if you do, try and look as cool as Boyz II Men.

Jodeci was not only a pioneer for its overtly sexual anthems, but also for its fashion-forward leather garments. The group showed up to the 1992 Billboard Awards donning ski masks, camo-print jackets, black leather boots, and even a machete—if that doesn't scream "A$AP" to you, we're not sure what does.