Fashion Favorites: Holly Madison Reflects on Her Most Iconic Looks
As Holly Madison reflects on her fashion history, there’s one decision she wishes she could change: the layers.
During the 2000s, the Playboy Mansion resident and reality TV star flaunted numerous daring outfits, yet Madison, 45, finds her more modest ensembles to be particularly embarrassing.
“There was that phase … when people would layer countless items that simply didn’t belong together,” she shared with Us Weekly. In a special video, she critiqued her own style in a game of Fashion Police, confessing that she’s guilty of pairing Y2K-style dresses over shirts on “low-rise crazy” jeans.
“For the most part, I look back and think, ‘I like that,’” Madison noted. “Even if it’s a bit campy or goofy, I understand the vision I had.”
Holly Madison in a Juicy Couture dress at the Playboy Mansion in 2005. Kevin Winter/Getty Images
For instance, she reminisced about the Juicy Couture strapless babydoll dress adorned with ruffles, which she loved so much that she bought it in three shades (pink, yellow, and black). “I recently wore it for the podcast because I enjoy showcasing nostalgic outfits,” she said.
Although it’s been more than ten years since The Girls Next Door debuted on E!, its memory remains vivid. The series, which ran for six seasons from 2005 to 2010, offered fans a glimpse into the exciting lives of Hugh Hefner’s three key girlfriends.
The “Girls Next Level” podcast host has a knack for resurrecting classic fashion statements. A standout moment includes the nude-hued naked dress inspired by a vintage Bob Mackie gown that she adorned herself for Hugh Hefner‘s 80th birthday bash in 2006. “I simply visited Hollywood Boulevard where they had all the stripper shops and found this sheer dress, then added a crystal bunny to it,” Madison recounted.
Bridget Marquardt, Hugh Hefner, Holly Madison, and Kendra Wilkinson at Hefner’s 80th birthday celebration in London in 2006. David Westing/Getty Images
She even made an appearance on the red carpet in the DIY dress, a simplified version of the bespoke attire that Mackie, 84, designed for former Playmate of the Year Monique St. Pierre, who wore it for the June 1979 cover of Playboy.
Years later, Hefner gifted the original to Madison, who was then one of Hefner’s three live-in partners, alongside Bridget Marquardt and Kendra Wilkinson, as showcased in the E! reality TV series The Girls Next Door.
“I still cherish it!” Madison exclaimed. “I adore fashion history, especially the legacy of the Playboy pictorials.” She further expressed, “My ultimate dream is to create a house with an impeccable closet to showcase my collection and include a mannequin, like a cozy museum for my beloved pieces.”
For more nostalgia, check out Madison’s exclusive Fashion Police video above.
