Inappropriate Outfits We Can't Believe Julia Roberts Wore

Julia Roberts gave us one of the most memorable inappropriate outfit moments in movie history when she strolled into a Beverly Hills boutique wearing Vivian Ward's famous minidress in "Pretty Woman." The actor's own experiences with dressing inappropriately haven't been quite as dramatic, but she's worn a few outfits that snooty saleswomen would definitely turn their noses up at. (Still, she should always be allowed to shop wherever she pleases!)

According to Roberts, her preference is to dress more like Vivian after her corporate raider-funded makeover. "My style is chic and effortless. I was told that once by a friend, and so I'm gonna just go with that," she told British Vogue. But unlike her ultra-feminine character, Roberts loves a good androgynous moment, such as the tailored men's Armani suit that she wore to the 1990 Golden Globes or the pinstripe skirt suit that she rocked on the red carpet at the same event one year later.

Roberts' mini skirt and jacket with gloriously girthy shoulder pads don't seem all that bad today, but her ensemble was described as ”Godfather III in drag” by fashion aficionado Mr. Blackwell at the time, per Entertainment Weekly. Even after topping the influential critic's worst-dressed list in 1991, Roberts didn't seem big on playing by anyone's fashion rules. This has often been to her benefit, but a handful of the "Mystic Pizza" star's sartorial selections are a bit mystifying.

While speaking to British Vogue about her '90s style, Julia Roberts said, "There were no fashion rules. You just wore whatever you wanted to wear. And I wore jeans and a white T-shirt all the time." These two staples were still very much a part of her wardrobe repertoire when the tabloids went wild over the scandalous start of Roberts' relationship with Danny Moder. Roberts met the cameraman when they were both working on the 2001 movie "The Mexican." Moder was still married to his now-ex Vera Steimberg at the time, and Roberts was dating Benjamin Bratt.

A source told People that Moder and Steimberg's marriage wasn't in a good place before he started romancing Roberts, but Steimberg seemingly didn't get out of the way fast enough for America's Sweetheart. And apparently, love can bring out Roberts' shady side: She grabbed some markers and took a sartorial swipe at Steimberg by writing the words "A Low Vera" on a T-shirt. She then threw on some jeans and a coat and made sure she was photographed wearing her creation.

It wasn't exactly the type of burn that you'd need some aloe vera for, but Roberts defended her gauche goading in a 2003 interview for O, The Oprah Magazine (via Oprah.com). "I stand by my T-shirt," she said. And despite publicly insulting Steimberg with a smirk on her face, Roberts told Oprah Winfrey, "You know what that was about? It was private."

When Mr. Blackwell named Julia Roberts the worst-dressed star of 1991, he deemed her the "tacky Tinkerbell from fashion Neverland," per UPI. It was a sad reminder of the excitement some "Peter Pan" fans felt upon learning that they would be getting a live-action version of their favorite pixie. But sadly, Roberts' Tink in the 1991 movie "Hook" was lacking that Disney dazzle — her sack-like garb was dull and shapeless. This wasn't her fault, of course, as she didn't design her costume, but the gown she wore for her first walk down the red carpet at the Academy Awards was also a drab letdown.

Roberts received her first Oscar nomination for her role in "Steel Magnolias." She looked every bit the movie star in the gorgeous wedding dress that she wore in the 1989 drama, which made her 1990 Oscars gown all that more disappointing. It was a greige Armani design with a wonky hemline — it was gathered between the ankles, making it look like Roberts had partially pulled up her underwear and gotten her dress caught in them in the process. The unfortunate placement of darts on the bust also made the garment appear more revealing than it actually was. 

Roberts' Oscars debut was a missed opportunity to establish herself as a style star who fashion labels would be lucky to work with — she really could have used some pixie dust to perk her look up.

Julia Roberts channeled Vivian Ward at the 2016 Cannes Film Festival in a black Armani Prive gown with an off-the-shoulder neckline. The big ... huge! emerald on her Chopard necklace was also totally something Edward would have gifted Vivian with. But before ascending the iconic stairs of the Palais des Festivals, Roberts made like Cinderella burning some serious glass and ditched both of her high heels.

When asked about her barefoot Cannes entrance on Australia's "Sunrise," Roberts said, "A lot was happening from my ankles up. Let's not forget all that. A lot of time and effort went into ankles up," (via Us Weekly). But by taking her shoes off, she ensured that everyone ignored all that work and focused solely on her bare soles.

Vanity Fair speculated that Roberts was rebelling against an unspoken Cannes rule that all female attendees must wear high heels. She also broke the official dress code, which states, "Elegant shoes, with or without heels, are required." However, Roberts later admitted to British Vogue that the reason she removed her shoes wasn't because she was trying to be edgy and ungovernable. "It was a statement: I didn't wanna fall down the f***ing stairs!" she said. At least she didn't try to pull a "Runaway Bride" by stepping onto the red carpet with sneakers on her feet — the Cannes dress code expressly forbids women from wearing trainers.

One day in January 2019, Julia Roberts woke up and decided that she alone could convince the world that the dreaded dress-pants combo — or "drants" — is a good look. At the Golden Globes that month, she wore a Stella McCartney ensemble that was great for a fashion cam fake-out. If the camera started at her face and slowly panned down, it would appear that she was wearing an elegant tulle gown with dainty crystal details. But there was a jarring transition from the waist down. The front of her delicate and romantic, champagne-colored gown suddenly disappeared and was replaced with a pair of black, tapered trousers. Much like her "Runaway Bride" character, she couldn't commit — but instead of fleeing from the red carpet, she said "I do" to two completely different outfits.

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The Golden Globes look landed Roberts on the Los Angeles Times' worst-dressed list, but undeterred, she wore a similar outfit to the Critics' Choice Awards a week later. Her Louis Vuitton take on drants featured a stiffer half-skirt attached to a sleeveless black top with lapels. The pants half of her outfit was white, and she switched back to black with her pointy-toed high heels. While the ensemble was more cohesive than her first attempt at the strange silhouette, it still landed her on USA Today's worst-dressed list, so perhaps she should have given up on it after one try.

When attending political events, some celebs probably feel pressured to dress more like the company they're keeping. And even if politicians' views are more of the liberal persuasion, they tend to wear conservative clothing. The black Greta Constantine dress that Julia Roberts wore to attend a fundraiser for President Joe Biden in June 2024 almost fit the bill. It featured a tea-length ruffled skirt and puff sleeves, details that few would consider daring. However, the garment's neckline took a scandalous nosedive — much like Biden's 2024 approval rating.

Roberts' color choice also provided fodder for Trump supporters, who made a predictable dig about it. "Wearing black for the funeral," read an Instagram comment from singer Joy Villa, who once sported a "Make America Great Again" dress at the Grammy Awards. A user on X echoed her joke, writing, "Julia Roberts wore a black dress to Biden's fundraiser thinking It was a funeral."

Roberts attended the event with her close friend and frequent co-star George Clooney, who also showed a little skin by leaving the top buttons of his dress shirt undone. However, Biden was probably far less offended by both actors' sartorial choices than he was by Clooney suddenly doing an about-face and calling for the president to give up his bid for reelection in an op-ed for The New York Times. But hey, at least he didn't do it with a t-shirt.