The Most Memorable Style Moments in Bad Boy Records' History

Image via Complex Original

Trend-setter B.I.G. starts one that would go on to be popularized heavy within his own house with the customized label jerseys. The petition to get the authentic piece hung up in the Rock and Roll Hall of Fame starts now.

Despite having three insanely steezy set-pieces, it's not hard to pick the strongest look in this video. Protagonist Puff woos a curious, beautiful princess (played by J. Lo, natch) and it's no secret he has her under pressure: he slid through the royal court in a gold tin foil suit, basically daring someone to say he wasn't killing it. The rest of the video is just as typically amazing as you'd expect from these two, starting with a Face/Off send-up where they present a flawless riff on the Troy brothers (Castor is one of the most stylish villains of all time, after all) that's equal parts endearing to their own brotherhood IRL and hilariously goofy.

Puffy and the fam loved leather arguably as much as they did eyesore suits, so it was no surprise when they built on Biggie's idea from the "Juicy" vid with the now iconic leather football jerseys in the iconic visual to "Can't Nobody Hold Me Down."

When the history tablets document the Shiny Suit Era, the amount of DGAF embodied in screenshots from this video will be the cover page. Puff and Ma$e are literally floating on everyone in the outlandish color-coordinated alphets —the blue joints might even be metallic denim—as they floss/do it one time for the dearly departed B.I.G. These were more than just attention-grabbing pieces; they defined a period of rap entering the mainstream and prospering with the riches that comes with it.

Three the hard way. So, G. Dep and Black Rob fizzled out. This was still a major moment, and this track was the hottest shit out for a time. Hip-hop fashion has long appropriated sportswear into its own thing, but has anybody ever put on for baseball (outside of fitteds, obviously) the way Puff does here? Dude's dressed like he's reporting live from the dugout during his verses and the look is extremely strong. How long until someone rediscovers this video and gets every single one of these trends back in rotation, if they haven't already?

It's no wonder The Lox wanted off Bad Boy. When you reflect on the group's discography and history today, you definitely don't picture them (reluctantly?) contributing to the Shiny Suit movement. Jada, Styles, and Sheek join Puff and Ma$e in holding Mariah down for her "Honey" remix in 14k glitterly gold sets. Bonus points for Sheek, who doesn't even have a verse standing out nonetheless in overalls. One strap down, naturally.

Besides Janelle Monae, it's been graveyard quiet for everyone else who was a part of this Bad Boy era—Ross doesn't count since he's technically not a part of the label, close personal relationship with Sean notwithstanding. But hey, at least they all looked like they were all about the business side of things in this Vibe spread.

This might be the shiniest video in the label's archive. Murda Ma$e even got The Lox to get their shine on in the Vegas-bright visual that over-matched the feel good vibes.

There was a time in the '90s when you weren't shit if you didn't have a steady stream of Karl Kani in your closet. Diddy was one of several top artists to model for the label, including Tupac, in an era when rappers and urban wear were in a symbiotic relationship. Now you're likely to see up-and-coming rappers in mainstream fashion ads, and top rappers sitting front row at some of the most exclusive fashion runway shows in the world. But back in '96, Diddy was merking it in the Karl Kani cokeboy look with unlaced Timbos.

Here's a nice vintage throwback with the two Bad Boy originals dressing quieter than usual by their standards but still looking too fly for two lords in the mid-'90s. Their bubble jacket game is too fresh, and with the Coogi layered underneath, it's only that much clearer that Biggie is the best-dressed dude in the history of the label.

 What else is there to say about what Frank White did for the sweater movement? When it comes to fashion, B.I.G. was extremely next and Coogi is just one of the many reasons we'll always love Big Poppa.

Bad Boy took numerous cues from the old mafia world in its outlook and style, and Biggie was a leader in dressing like a Don. Pinstripe suits, bowler hats, walking sticks, and pinky rings were all par for the course, and in case you weren't aware that Frank White and Diddy were bosses of the game, one look at their mobbed out power suits quickly changed all that.

This Lord/immaculately dressed #menswear "butler" was one of the highlights of the early aughts Bad Boy era. Part of the anticipation of a new video from the team was seeing what ridiculous Carlton-esque dance he'd break into in his wingtips. Who do we have to plead with to get a Fonzworth cameo in the next MMM visual?

Of course, Biggie's legendary style co-signs and trend-setting extends beyond Coogi. The two top dogs at Bad Boy loved their Versace silks and linens, arguably putting them on the map for the rest of the game. It's no accident that Versace's and Bad Boy's rise went hand-in-hand, as the rap label made the clothing label a status symbol for other rappers and style-conscious dudes to aspire towards.

Mon-TANUH may not be the most "lyrical" rapper (read: not broke) but he's one of the freshest in the business off of his impeccable pelt game alone. Remember, Roc Nation and G.O.OD. Music were among the labels clamoring to sign him, but when Bad Boy and MMG joined forces for the steal it was an unmitigated win in the style draft. His pelt and Versace game are strong additions to the label, and only build on an already legendary reputation.

The timelines seem fuzzy now but yes, before he "responded to God's call," Ma$e was actually still around to witness his big homie's clothing brand take off. Who knows how many tandem diddy-bops in SJ velour suits we were robbed of by his departure.

Pharrell and his streetwear partner-in-crime Nigo were definitely instrumental in bringing A Bathing Ape to the world of hip-hop. But it's a little-known fact that Biggie was on the niche Japanese label wave well before the early 2000s when BAPE really popped off in hip-hop. In '95, complete with Versace shades and a beige turtleneck with the center seam, Biggie Smalls was already proving Jay Z correct when Hova later rhymed, "BIG predicted this shit exactly."

Everyone's making a fuss over Kanye showing out in Vogue, but don't forget Sean Combs scored fashion's first big nod to hip-hop back in '99. Under Annie Liebovitz's lens, Diddy swagged out on a hundred thousand, and alongside the queen Kate Moss at that. This was a huge look for hip-hop, and if you think high fashion and the rap game are just getting in bed together in this decade, you better do your homework and recognize Puff's innovating breaking down of walls.

Puffy's all-white Labor Day parties in the Hamptons have been the stuff of legend for decades now, and they're still a season-ending event that people do everything they can to make it into. It makes sense that he would sign French Montana years later; Diddy is the original cokeboy.

No, Sean didn't create this amazing phrase. But he did popularize it, and better yet, put it on his clothing label-proper. Words to live by, words to wear.

Just imagine how many more carpets this dynamic duo would have slayed over the years. This is achromatic, proto-KimYe carpet stunting at its finest. They may have been rocking opposite ends of the color palette, but Diddy and Biggie were murdering the suit game like no other members of hip-hop at the time.

This is one of the most iconic, trend-setting videos of all time because it's super simple and yet so damn effective. While Bad Boy videos would later be known for their Michael Bay-level bombast, the visuals for the remix of Craig Mack's hit "Flava in Ya Ear" is simply the best rappers in the game (at the time) looking cool in front of the most basic background imaginable, off-set on that achromatic wave by all-black-everything dress code. Thus, the whiteprint for simplistic videos was born.

Choosing the most stylish R&B group of all time (or at least, the '90s) would be tough, but one thing's for sure: 112 has got to be a part of the top ten conversation. Slim and the gang fit the Bad Boy aesthetic perfectly, opting for leather more often than shiny suits, but in a "sliding into your girl's DMs" if DMs were around then manner that meshed with the rest of the label. Definitely not the hardcore, tough-guy leathers the Lox favored.

In the rap style spectrum of color, there's Shiny Suits, and on the completely opposite end, whatever new era Bad Boy is doing here. Puff's come a long way from the vibrant Fifth Element joints. He, MGK, Los and Red Cafe join French Montana for this clip where they take all-black-everything to even shadier extremes. They all look like supervillain underdwellers plotting world domination, but it's working for them.

Only Puff Daddy would stage both his musical comeback and the return of the moniker we all never actually stopped calling him by gathering all his fellow A-list friends to...mob outside the parking lot of a chicken joint. You thought the rein of fearless, in-your-face swag would be over by 2014? Fried chicken and fancy furs, Bad Boy's still on top. Everyone's fur game in this video is impeccable, from Rozay down to Ashanti. But the real next-level swag on display is youngest Combs male Christian effortlessly inheriting the stunt-genes while rapping a few bars for pops. Very touching.