Demi Moore's Most Inappropriate Outfits To Date

Brat Pack beauty Demi Moore doesn't need fabric to start a fashion trend. While pregnant with her daughter Scout Willis in 1991, she rocked nothing but a hand bra for her controversial cover of Vanity Fair. Some critics found this distasteful, and the Publix grocery chain even refused to sell the issue. But it made other mothers-to-be wish that they, too, could look like a glossy fertility goddess, and soon other celebs with baby bumps were posing in their birthday suits. Unfortunately, when given more options than her arm and strategic poses, Moore has made some outfit choices that aren't quite as glamorous.

The "Feud: Capote Vs. The Swans" star usually delivers the goods on the red carpet, such as when she showed Björk that a swan on a dress can look chic and sophisticated. Moore has also rocked the same outfit as a much younger celeb, proving she can look just as good in it. Speaking on behalf of her fellow sexagenarians, Moore told People, "We don't want to look matronly or not feel sexy." However, she's not as fond of red-carpet fashion as you might think. She said of getting glammed up for events, "I still feel like a little kid who gets to dress up and who I am at heart is a grubby 12-year-old boy who really likes to just be comfortable and wear baggy clothes." Her preference for cozy apparel may help explain why she suffers the occasional style slip-up while playing dress-up.

Demi Moore wore a disastrous DIY outfit to the Oscars

Demi Moore was way ahead of the athleisure trend at the 1989 Academy Awards. The ensemble she put together included — gasp! — a pair of Spandex bike shorts. While it can be brave to buck tradition and go where no fashionista has gone before at a Hollywood event, there's a reason few celebs have attempted to pull off that particular silhouette on the red carpet. Something about the shorts' weird length just makes it impossible to take them seriously as formal wear. However, Moore made a futile attempt to fancy hers up a bit with some lace trim.

Of her personal style, Moore told InStyle, "I tend to go towards classic with a twist, and I quite love vintage." We've already covered her Oscar look's twist, and it did, indeed, include a vintage element as well. Her velvet, corset-style bodice would have looked fine paired with a matching skirt, and perhaps Moore knew this in the back of her mind; gold fabric attached to the back of her top created a mullet skirt that was appropriate for the era. Unfortunately, the outfit keeps landing her on worst-dressed lists, including The Sun's retrospective of "The most awfully memorable Oscar gowns of all time." Time magazine wrote of the look, "It's like someone locked her in the Tower of London for months with nothing but a stationary bike and a mood board for company, and the mood board became self-aware."

Demi Moore's indecent promotional stunt

It's hard to imagine a female actor today appearing on a late-night show and letting the host ogle her body after undressing in front of him. But that's what Demi Moore did in 1995 to promote "Striptease." She strutted onto "The Late Show with David Letterman" set wearing a bra and panties partially covered by cards with numbers printed on them. As Letterman rattled off a list of the "Top 10 Least Popular Stripper Names," Moore removed the card with the corresponding number he called out, revealing more of her body until all she was left wearing was her underwear, high heels, and a skirt of blank cards. She pretended to struggle with the final card before ripping off the entire skirt and doing a sexy dance. The names on the list included "Stripper Gore," "Mrs. Charlie Sheen," and "Nude Gingrich."

Moore hadn't yet finished filming "Striptease" at the time, and she told InStyle her future scenes were on her mind during her performance for Letterman's hooting audience. "I was pretty much just freaking out because I knew in a very short matter of time I would be wearing floss up my butt," she said. Oddly, by allowing herself to be objectified, Moore possibly helped other female actors negotiate better salaries in the years to come. Of her $12.5 million payday for "Striptease," she told Interview, "From the day they offered me that much money, it changed the way women in Hollywood were viewed."

Did she get Punk'd by her stylist or something?

Among the controversial decisions Demi Moore has made is her rocky marriage to Ashton Kutcher. When she showed up at the New York premiere of "Charlie's Angels: Full Throttle" in 2003, Kutcher accompanied her, but unfortunately, he didn't surprise his date by ambushing her with a camera crew and telling her that she'd been "Punk'd" by her stylist.

Moore had on a green chiffon dress with ruffled layers. The color was gorgeous on her and the dress was pretty, but underneath it, she wore a semi-sheer lace bra and fishnet pantyhose. The top of the dress was pulled down to expose her bra, and the result of this sartorial striptease was chaotic and confusing. If "Fashion Police" had existed back then, Joan Rivers probably would have wise-cracked that Moore's stylist deserved to be fully throttled for letting her step out in that outfit. 

In some photos from the premiere of the "Charlie's Angels" sequel — which was supposed to mark Moore's big career comeback — the actor was also wearing a green velvet coat that looked like it was borrowed from the Lucky Charms leprechaun. The result of pairing it with the rest of her outfit was not magically delicious.

Demi Moore wasn't lying about loving overalls

The outfit Demi Moore put together for the opening night of "Hedwig And The Angry Inch" at Hollywood's Pantages Theatre was "Punky Brewster" meets "Midsommar." She attended the play in a pair of burgundy corduroy overalls, a yellow-and-white striped turtleneck, and a denim jacket. Although her look was uber-casual, she wore her coat draped over her shoulders like a fashion girlie doing a street-style photoshoot. Moore randomly wore a tiny floral crown perched atop her head, and her hair was styled in pigtails. Moore is close friends with Soleil Moon Frye and was even the "Punky Brewster" star's doula for all four of her pregnancies, so maybe the look really was inspired by the funky style of Frye's spunky sitcom character.

OK! had a scathing review of Moore's look; the outlet deemed it "baffling ugly." But maybe she was just in a rush and grabbed the first items of clothing she saw in her closet. Apparently, it's packed with overalls. Moore told People this is her favored attire when visiting her sprawling ranch in rural Idaho. "When I'm in Idaho, it's generally overalls all day, every day," she said. Go Fug Yourself suggested that she had been somewhere more befitting her garb before heading to the premiere. "I am real worried that one of her handlers found her wandering aimlessly in a meadow, and tricked her into getting in the car," the blog wrote.

Her peek-a-boob mishap at Paris Fashion Week

Demi Moore looked très chic in the off-the-shoulder dress she wore to the Saint Laurent Womenswear Spring/Summer 2024 show during Paris Fashion Week in 2023. However, her bra was but a "Ghost" (cue "Unchained Melody"). Moore's clingy black gown was crafted out of diaphanous material through which her black underwear was visible. A foldover neckline covered her chest area, but when Moore raised her arm to rearrange her long, silky hair, this exposed one of her breasts. If Moore noticed that a photographer had captured the wardrobe malfunction on film, it didn't seem to bother her.

At least the minor mishap got people talking about her outfit instead of speculating about the state of her face. After she walked the runway for Fendi at Paris Fashion Week in 2021, OK! consulted with four doctors to get their opinions on what she had possibly done to make her face look so different. But when she appeared on Naomi Campbell's YouTube series, "No Filter With Naomi," and reflected on what it was like to be a supermodel for a day, all Moore could talk about was what a great time she had. "It really was like a teenage fantasy fulfilled," she gushed.