For me, the fascinating thing about seeing Diddy all dapper is that I still remember when he didn't even have a good suit. Because I had to force him into one.
I mean how incredible is this 2010 @iamdiddy twitpic?
If this picture is worth a thousand words then six of them are: Celebrity is like its own race.
Most of the people pictured above wouldn't have anything to do with the other if they weren't all megarich. But since they are, they're all crammed together in this corner having the time of their lives at The Costume Institute Gala, fashion’s biggest night hosted every year by Vogue editor-in-chief Anna Wintour.
You've got 58 year-old Oprah Winfrey, who does not get jiggy with that rap music. Jamaican Brit Naomi Campbell who went from humble beginnings to supermodeldom to living in Moscow luxury with her Russian billi beau, Vlad. The guy in front of Diddy is DJ Cassidy, the A-list's spinner of choice who was named the official DJ of our ultra cool POTUS. And lastly there's Pharrell Williams, who's like hip-hop's Richie Rich living at a savant-like pitch that few can hear. And Sean "P. Diddy" Combs is the eye of this A-list storm.
When I was working in Tommy Hilfiger PR back in the days when TH was the fave hip-hop brand, all the rappers would come up to the building on 39th Street to get free gear.
We'd take them up to this place called "The Cage," which was a secret room on the 13 1/2 floor. Basically it was an oversized closet between the 13th and 14th floors only accessible by a rickety staircase. When 6'7" Snoop Doggy Dogg (as he was then known) visited, he had to keep his head slightly bowed the whole time like a grown-up in a treehouse.
We called it "The Cage" because the walls were inexplicably covered with metal chicken wire. It was always an overflowing-with-samples mess, mostly because it was my lowly job to organize it.
The chaos of clothes really annoyed Tommy, who was generally a dream boss. So whenever I saw him coming down the hallway that led to the secret door that led to the secret sample room, I'd immediately change course to avoid him because I knew he would shame me by saying, ever so calmly, "Erica, can you tell me why 'The Cage' is such a mess?" and I'd have to avert my eyes and mumble the oft-told lie, "I'm on my way to clean it right now."
Mostly I didn't clean it because we only took hip-hop heavyweights in there and they didn't care that everything wasn't stacked to showroom standards. They just wanted in, by any means necessary.
In the late 90s, getting an invite to The Cage, usually from Tommy himself or his brother Andy, meant you were somebody, yo.
And what was it like to take a VIP crew of huge, heavily tatted, blingy b-boys to The Hilfiger Cage? The hip-hop equivalent of seeing a horde of fashionistas lose their minds at a Blahnik sample sale -- only, if you can imagine, less violent?
On this particular occasion, when Puff Daddy (then) and his 15-deep crew came through to load up on oversize jerseys and puffy (!) bomber jackets, we'd just had a fashion show and there was a rack of suits being completely ignored in the sample scooping free-for-all.
"Hey, Puffy," I said, "why don't you take one of these?" This was back in the days when he dressed like this.
I'm quite sure he cocked his head and gave me a similar look from behind his shades, which he was wearing in the dimly lit Cage. Still, I pulled a suit off the rack and checked the size.
"Forty-two regular. That would probably fit you. Try it on." Again he looked at me like I was nuts. I can't remember him ever saying much, but he probably said something like, "Nah nah, that ain't me."
And yet I persisted.
"Puffy, this is a gray flannel chalk stripe suit. This is classic. You need to have a suit like this in your wardrobe. Just try on the jacket and see if it fits!"
As the Bad Boy crew stood around telegraphing "You're playing yourself" vibes, Puffy succumbed to my pressure. He slipped off whatever sloppy XXXL nonsense he had on and slipped into the jacket.
He shook his shoulders to get a feel for it, looking around self-consciously at his uncomfortably quiet crew, and seemed somewhat perturbed that I was putting him in such a position.
I pressed on because I knew this was a rite of passage for him. And better he had the experience with me, a 23 year-old black girl who understood exactly who he was and how influential he would soon be rather than a white PR girl who might, inadvertently or not, condescend to him.
I'd known Russell Simmons since high school and had gotten the Hilfiger job after sitting next to Tommy one night at Bowery Bar, the hotspot du jour then, when he came in after the CFDA awards with Russell and Leonardo Dicaprio.
Me after an hour of chatting: "I need to find a job. Maybe I should work in your PR dept."
Tommy: "OK." I started the next week.
As part of Russell's circle, I'd been around a lot of these hip-hop "playa" types when they were just coming into their wealth with no one to guide them. And sometimes I became that guide.
When one of the industry ballers bragged that he’d dropped ten grand at Calvin Klein on 5th Avenue one Sunday after brunch, I said, “You do know that VIPs come up to Tommy and custom order suits from a special catalog and they get them wholesale, don’t you?” His response? Silence.
A few weeks later, I had him come up to Tommy and when his order came in, I sent him the suits but not the bill.
At that time I was recent college grad. Translation? Poor. But as a middle-class black girl who'd spent my junior year cycling around Oxford in penny loafers, I knew what fork to use when or why a sorbet might arrive before a main course or how to find my way to the Louvre without speaking the language.
And when I didn't know something, I'd ask someone who did. Which is what you do when you feel like you have the right to be wherever you are.
But as any woman who has driven around in circles with a man who refuses to ask for directions knows, saying "I don't know" doesn't come easily to those with male genitalia, especially rich black men who find themselves in unfamiliar environs.
I'd once been out to dinner with music mogul Andre Harrell, Puffy's former boss when he demanded the waitress bring him a "chardonnay red." When she very politely suggested he try a chardonnay white, Andre took an affronted tone and, to my utter mortification, said, "I asked for a chardonnay red. Give me what I asked for!" Oy vey.
The waitress returned looking very apologetic. "I'm so sorry sir, we're out,” she said, head bowed like a geisha. “Would you like to try a glass of port on us?" That was something Andre had never heard of, but he took a sip, swilled it around his mouth like a wine connoisseur and deemed it acceptable.
The TH gray flannel suit was Puffy's port and, knowing one day it would become an acquired taste, I said, "See, it fits! Anyway, it's free. Just take it!" And before he could refuse, I quickly zipped the whole suit into a garment bag and foisted it on him.
Now look at Mr. Sean John Combs. Clothing mogul. Campaign model. CFDA award winner. Anna Wintour bestie. Zac Posen backer. With a wax figure in Madame Tussaud’s that looks like James Bond.
And he’s had plenty of company along with him for the ride. Steve Stoute, a former record executive turned branding visionary, has published a new book called “The Tanning of America: How Hip-Hop Created a Culture That Rewrote the Rules of the New Economy” with a foreword by Vanity Fair editor-in-chief Graydon Carter.
Biggie’s 15 year-old son, Christopher Wallace Jr., co-starred in the indy flick "Everything Must Go" with Will Ferrell. Ice Cube, the former head of NWA, is talking up the Eames. And Hip hop mogul Russell Simmons is now more famous for his devotion to yoga. Oscar-nominated rapper Queen Latifah has a line of Covergirl. Kanye sits front row at the Paris shows and spits "Hermes verses" about G5 jetting.
If we haven’t landed in “post-racial America” yet, I feel like we can see the runway lights from here in large part, thanks to the hip-hop revolution and its Prada-wearing foot soldiers and their now de rigeur fancy suits.