Julia Roberts Outfits That Totally Missed The Mark

Though Julia Roberts has a slew of chic outfits in her fashion repertoire, like many other seasoned Hollywood performers, she's experienced a few fashion missteps. Even the star herself has admitted not every outfit has been her best. When asked by Yahoo! Style if she'd made any style mistakes over her decades-long career, she responded, "Oh, I'm sure I've made hundreds, but you know, when I look back now, I'm glad I did." She added, "I just wore such crazy things. Bright tights, some second-hand naval officer jacket with a Rolling Stones t-shirt and a pair of boots. I thought I was ready to go. I'm so glad I had that time in my life to just really shop at thrift stores in Manhattan and wear really crazy s**t." The "Pretty Woman" and "Mystic Pizza" actor also told W of what she's learned about fashion over the years, "You have to wear what you like and not what you get talked into!"

That said, a glance at Roberts' fashion timeline reveals she's donned several outfits we can only imagine required some convincing. Amongst her biggest fashion faux pas? Repeatedly dressing down for formal award shows early in her career and making odd shoe choices on the red carpet. Though it gives us no "Satisfaction" to say, these Roberts' outfits totally missed the mark.

Julia Roberts rocked a hair color similar to her natural hue at the 1991 Oscars alongside then boyfriend Kiefer Sutherland, and an all-black number that didn't work for a high-profile event. The high-neck, long sleeves, and pants over semi-sheer, black hosiery gave us Wednesday Addams costume vibes and it felt like a missed opportunity to have fun and make statement as an up-and-coming actor. The black on black also made it difficult to see what she was wearing in photos, forcing her to blend into the shadows.

1991 wasn't the only year Julia Roberts had a fashion misstep at the Oscars. The year prior, she also failed to make a fashion statement in a dull, neutral dress. Though the color was ahead of its time (it gave us Pantone's 2025 Color Of The Year Mocha Mousse vibes), it was underwhelming for one of the formal events on the planet. The simple number needed better tailoring around her waist and featured an odd gather at the bottom front, which looked more like it had bunched up than a chic style choice.

At the 2000 "Red Planet" premiere, we didn't know where to look with Julia Roberts' black, green, pink, and orange dress adorned with a bright floral print and knee-high boots. The busy garment was not a match for her leather shoes, especially given that this event happened during the summer. A classic and sophisticated pump in nude, or one of the colors on her dress, would have elevated the look in a far chicer way.

When Julia Roberts hit the L.A. Film Critics Awards red carpet in 2001, she paired a shiny, leather-look top with a plaid knee-length skirt and black boots. But, again, her tall boots didn't work with the outfit (particularly the length of the skirt) and the mixture of colors and textures felt confused. Her top was a more pink-y red than her skirt, so the two clashed, and the criss-cross patterns on her skirt were too much next to her shiny top and shoes.

Julia Roberts attended the Drama League Awards Ceremony and Luncheon in 2006 — but someone needed to tell her clothes that. The actor seemed better dressed for a casual lunch with friends in a daytime, floral dress with sheer sleeves, and her shoes weren't red carpet appropriate. She wore a very low heel, practical brown pair with a Velcro strap, which looked more like comfortable walking shoes than dressy, luncheon footwear. Even ballet flats would've been a better choice, as these clunky accessories aged her.

Not every red carpet dress needs to be low cut and adorned with rhinestones, but Julia Roberts' matte brown top, skirt, coat, and peep-toe heels combo looked too simple and underwhelming at 2001 SAG Awards. This is even more evident in photos where she's seen posing next to her then-boyfriend Benjamin Bratt, who wore a well-tailored suit and tie. The year prior, Roberts wore a chicer and more formal strapless, brown dress and black wrap to the People's Choice Awards and, if we were her stylist, we'd have suggested swapping those outfits.

Julia Roberts wore a beige, shirt dress with a long, black tie in 2025 that did nothing to compliment her figure or skin tone. For one, the bland hue washed her out, while the garment itself was totally shapeless, as if someone had draped a blanket over her. This look demonstrated the importance of tailoring when styling an oversized shirt because, had it been a little more fitted around the waist, it could have worked. "The whole fit looks awkward, like something is missing. a belt with the dress would've been more flattering," one Instagram user wrote.

In 2002, Julia Roberts was snapped in a makeshift T-Shirt, jeans, boots, and a black coat. The outfit wasn't unflattering or outdated, but her top read, "A low Vera," which appeared to reference her now husband Danny Moder's first wife Vera Steimberg (who he was married to when he began dating Roberts). When asked about the tee on "The Oprah Winfrey Show," Roberts hit back, "It was private. I stand by my T-shirt." However, it felt unnecessary and a low blow to take another woman down, which went against Roberts' sweet persona.