‘It’s Giving…Janet Jackson Vibes!!’: Sherri Shepherd Shares Throwback Photos from Her Younger ‘Days of Sneaking Into Clubs’

Sherri Shepherd might be a classy beauty who prefers to cover up now, but back in the day, she had her moments of showing some skin!

The daytime TV host uploaded two throwback photos that were combined into one post that showed her gorgeously rocking crop tops, big wasted belts, and high heels.

Sherri Shepherd’s throwback look is compared to a Fly Girl from “In Living Single.” (Pictured: @sherrishowtv/Instagram)

Shepherd’s picture on the left showed her in a two-colored blazer jacket with a black tube top, jeans, red boots, and an obnoxiously large belt. The photo on the right showed her wearing an all-black ensemble featuring a black and gold hat, black heels, and a black belt. 

Fans were also able to see the 55-year-old stylishly rocking the popular mushroom cut hairstyle. 

“Today Sherri threw it back to the day of sneaking into clubs in your best Wilsons leather,” the caption read. 

Shepherd’s photos screamed the ‘90s, and several fans seemed to think so too, for the post received over 200 comments from individuals who also shared their love for the retailer Wilson’s Leather. 

“Wilsons leather. When you had a jacket from Wilsons you were the s–t! I had a blue leather fringe”

A few fans also compared Shepherd’s look to music icon Janet Jackson, who made a surprise appearance on her talk show, “Sherri” last December. Many also compared her to a Fly Girl on the popular ‘90s sketch comedy show “In Living Color.”

“It’s giving fly girls/ Janet Jackson vibes!!”

“Giving… In Living Color Fly Girl Vibes!”


“In Living Color” was created by the ever-so-talented Wayans family and aired its first episode in 1990. The series ran for five seasons until its end in 1994. 

While the show’s main focus was geared toward making a live audience laugh with their comical skits, the all-girl dance group slowly became a popular piece in the show. 

The “White Men Can’t Jump” actress Rosie Perez choreographed the ladies’ dance routines for the first four seasons of the show. After her exit, Arthur Rainer became the main choreographer with the help of Lisa Joann Thompson and Deidre Lang as assistant choreographers. 

Throughout the show’s run, “In Living Color” oozed with up-and-coming talent, including actors, singers, and comedians who have now made their mark in Hollywood. 

During the show’s third season, Jennifer Lopez joined as a Fly girl along with the Grammy Award winner Jamie Foxx, who joined as a comedian. 

Some other A-list celebrities who got their start on the popular show include Jim Carrey, “Peeples” actor David Alan Grier and “Selective Outrage” comedian Chris Rock. 

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