Fashion Police: Holly Madison Looks Back on Her Most Iconic Styles

When Holly Madison considers her past fashion choices, she only has one regret: layers.

In the 2000s, the Playboy Mansion denizen turned reality star wore her fair share of revealing outfits, but Madison, 45, considers her most covered-up looks to be by far the most cringe.

“[There] was that trend … where you would layer a million things that have no business being layered,” she told Us Weekly. In the exclusive video, she played Fashion Police​​ — with herself — and admitted that she’s guilty of rocking Y2K-era dresses over shirts over “low-rise crazy” jeans.

“Usually, I look back on my stuff and I’m like, ‘I like it,’” Madison said. “Even if it’s camp or silly, I know what I was going for.”

Case in point: the Juicy Couture strapless babydoll dress with ruffles that she loved so much she bought it in three colors (pink, yellow and black). “I wore it recently for the podcast, because sometimes I like to bring out throwback outfits,” she noted.

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The “Girls Next Level” podcast host has a history of reviving iconic fashion looks. A sparkly standout is the flesh-colored naked dress inspired by a vintage Bob Mackie gown that she bedazzled herself for Hugh Hefner‘s 80th birthday party in 2006. “I just went to Hollywood Boulevard where they have all the stripper stores and got this see-through dress, and then I put a crystal bunny on it,” Madison explained.

She even hit the red carpet in the DIY dress, which was a shorter version of the bespoke look that Mackie, 84, custom designed for then–Playmate of the Year Monique St. Pierre to wear on the June 1979 cover of Playboy magazine.

Decades later, Hefner bought the original as a gift for Madison, who at the time was one of the late publisher’s three live-in girlfriends, along with Bridget Marquardt and Kendra Wilkinson, as immortalized on the E! reality TV show The Girls Next Door.

“I still have it!” Madison gushed. “I love fashion history, [and] I love the history of the Playboy pictorials.” She added: “My dream is to build a house with a perfect closet where I can display a lot of things and have a mannequin, like a little museum of my favorite stuff.”

For more throwbacks, watch the exclusive video of Madison’s Fashion Police above.