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will smith cindy crawford

Cindy Crawford interviews rapper Will Smith on the set of the 'Fresh Prince of Bel-Air' in 1990.
Photo: MTV

Season: 2 Episode: 6
Title: Winter '90
Original Airdate: 11/28/90
Appearances: Will Smith, Lady Miss Kier (Deee-lite)

DEMYSTIFYING FASHION: CINDY HANGS OUT WITH WILL SMITH ON THE SET OF 'FRESH PRINCE'

The thing about Cindy was that you could send her anywhere. She's as down to visit a European atelier as she is to visit the set of The Fresh Prince of Bel Air. In this segment, Cindy hangs out with Will Smith at the “mansion” for a fourth wall-shattering tour of the brocade furniture-filled set, and for a snoop through Will’s wardrobe. This is 1991, so Will’s closet is filled with double-breasted blazers with enormous, peak lapels featuring wooden Afrocentric brooches, crazily patterned button-down silk shirts—like, straight up Cuba Gooding Jr. in Boyz 'N The Hood—and another shirt that I swear is the precursor to the dollar-sign-all-over-print that would dominate streetwear in another ten years. There's also a LEATHER black and white starter jacket that comes with a matching hat (also leather). The two play dress up, and it’s enjoyable because Cindy’s a nerd. Seriously, she brings a pair of Jordan Vs to show Will (Will is wearing Jordan warm-ups) and asks for his approval. She’s so proud of herself for not having removed the tags and wants scene cred because “Humpty Dumpty told me that.” Will then loses his mind laughing at her: “It’s just Humpty!” referring to the alter ego of Shock G from Digital Underground. It’s fantastic.

You know how models love talking about how awkward they were as kids and you never quite believe them? Well, in this moment you do. You see the relatable side of Cindy, and it is charming as hell. It makes you appreciate how young Cindy is—college-age in fact—and it’s the one moment that you see her socialize (albeit with an actor/rapper) in a youthful, peer-group context. It's a surprisingly revealing moment between two super-professional, famous young adults and another way of contextualizing fashion without designers, labels and the runway.

+ WATCH CINDY AT 'FRESH PRINCE' WITH WILL SMITH


MUSIC AND FASHION: LADY MISS KIER’S WORDS OF WISDOM

retro fashion

Lady Miss Kier of Deee-Lite in Patricia Field's original store in 1990.
Photo: MTV

The frontwoman for Deee-Lite, Lady Miss Kier, sits in Patricia Field’s boutique with an immaculately flipped coif and signature vintage duds. While we couldn’t get the video, I wanted to show you the interior of the store, because this is clearly not Pat’s current storefront on 302 Bowery or the new, new storefront that’s opened a few doors down, but House of Field! It’s the original shop on 8th Street between 5th Avenue and University Place, Pat’s first location for 40 years (Pat also lived on the top floor), before she moved in the early aughts.

We speak to Lady Miss Kier about the huge ’60s revival in 1990, when everyone was dripping in Flower Power prints like daisies and sunflowers; John Lennon sunglasses; denim flares; and A-line mod shift dresses, because she embodies the decade visually and gives great, timeless advice. “Gravitate towards the things that you like, and feel comfortable in,” she says, “but don’t let anyone else tell you what’s in or what is out. Everything is taken from the past, but it’s really just knowing when to bring something that’s a classic back. Nothing is really new, it’s just how you bring it back.”

Lady Miss Kier knows fashion. She moved to New York to study Textile Design at FIT and subsequently dropped out to create clothing for her DJ friends before creating the look of Deee-Lite, including her characteristic groovy, zip-up catsuit/platform shoe/thick headband aesthetic.

MUSIC AND FASHION: PRINCE OPENS A CHAIN OF NIGHTCLUBS AND BOUTIQUES

prince glam slam

Prince's night club, Glam Slam in 1990.
Photo: MTV

True story: From 1989 to 1995, Prince had a chain of clubs called Glam Slam that also featured a boutique with the same name. Prince put Minneapolis nightlife on the map with Purple Rain by hanging out and filming at a local club called First Avenue, and he wanted to create a similarly memorable atmosphere called Glam Slam for its sequel—Graffiti Bridge.

There were four Glam Slams—the original in Minneapolis, Minnesota; one in Miami (Glam Slam East); one in Los Angeles (Glam Slam West); and one in Yokohama, Japan. All have either closed or are now unaffiliated with Prince, but the part that’s most interesting is the inclusion of a gift store in each of these nightclubs (MEEEEEEEEP!!! Can you EVEN imagine a string of boutiques stocking Prince-approved sundries that you can drunk-shop? Nuts!). The offerings were created by Helen Hiatt, the costume designer for Graffiti Bridge, and are largely based on the wardrobe for the film. There are loud suits, chain fringe leather jackets, jackets decorated with license plates (this was a HUGE design concept in the ’90s for reasons that remain mysterious [see also: the appeal of stuff made from seat belts]), and Prince symbol belts and jewelry. It sort of reminds me of how that irritating, guylinered bro-gician Criss Angel has a store in Vegas, except that Prince’s stores are infinitely cooler, and I can’t help thinking that a thoroughly curated museum collection would be an important contribution to the music/fashion canon.

+ CHECK OUT MORE PHOTOS FROM EPISODE 6

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cindy crawford richard gere

Cindy Crawford interviews actor and boyfriend Richard Gere at the Gianni Versace AIDS Benefit in 1991.
Photo: MTV

Season: 3 Episode: 11
Title: Best Of Edition
Original Airdate: 11/28/91
Includes segments from:

  • Cindy Hangs Out With Will Smith On The Set Of Fresh Prince (Episode 6)
  • VIDEO | PHOTO

  • Gianni Versace AIDS Fundraiser (Episode 7)
  • VIDEO | PHOTO

  • Cindy Crawford's 1991 Calendar Shoot (Episode 8 )
  • VIDEO | PHOTO

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Featured Comment

I love these two as a couple. What a festive way to celebrate two important events in their life. Mariah looks like a dream.

Posted by Journey on Mariah Carey And Nick Cannon Shut Down Disneyland To Renew Vows In Cinderella-Themed Ensembles
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