Julia Roberts' Chic Style Transformation Proves She Just Gets Better With Age

Back in the late '80s, when Julia Roberts had her breakthrough thanks to the films "Satisfaction" and "Mystic Pizza," nobody could have predicted she would become one of the most successful stars of her generation. '90s projects like "Pretty Woman" and "Notting Hill" turned her into a Hollywood staple, and the 2001 biographical film "Erin Brockovich" made her an Academy Award-winner. Since then, Roberts has starred in numerous blockbusters, showcasing the versatility of her acting skills through the decades. But while her career is undeniably impressive, so is Roberts' style.

Since rising to fame, the actor has pushed the boundaries of fashion, all while looking fabulous and feeling comfortable. In 2017, she told W, "I don't follow fashion per se, but I love it," adding that when it comes to industry events, it's all about being yourself. "You have to wear what you like and not what you get talked into," Roberts shared. And one thing that Roberts' style evolution shows is that her fashion preferences may have changed, but her style always remained authentic.

Quite early on in her career, Julia Roberts became the celeb who actually popularized the oversized suit aesthetic. Roberts famously showed up to the 1990 Golden Globe Awards in a gray Armani men's pantsuit, pushing the norms of what women were expected to wear to prestigious award shows. In the early '90s, Roberts' style was all about mixing form-fitting and oversized pieces, thereby creating interesting and unexpected silhouettes. Apart from her cool-girl style, the "Steel Magnolias" actor was also known for her beautiful curls.

By the mid '90s, Julia Roberts was in her late 20s, and her style was headed in an even quirkier direction. While Roberts stunned in simple and sophisticated looks, the actor had a particular fondness for fun patterns and prints. Whether she was mixing stripes or wearing jackets with bold floral patterns, Roberts pulled off the dramatic looks with ease. The star never shied away from a statement look, but most of her fashion choices still prioritized comfort, consistently proving that fashion doesn't have to be painful.

The late '90s were a time when fashion was perhaps its most whimsical, as it was slowly shifting towards the craziness of the Y2K era, yet still holding on to the worn-in and thrifted coolness plenty want to emulate today. During this period, Roberts served as a great example of what many miss in fashion today. The "My Best Friend's Wedding" actor perfected the art of hopping between various styles, as she simply dressed in pieces she liked, regardless of whether they were sparkly statement dresses or delicate floral 'fits.

The early aughts brought an important shift in Julia Roberts' career, as the actor won an Oscar in 2001 for her work on the biographical drama film "Erin Brockovich." For the big night, Roberts went with a black and white Valentino gown, one that has become her most talked-about look. "I guess the one that gets the most commentary is probably my look for the Oscars for Erin Brockovich," the star told People in 2017. The timeless gown is definitely among the Oscars dresses from the early aughts we'll never forget.

Once Julia Roberts was in her late 30s, the actor slowly shifted to more glamorous and timeless red-carpet fashion. The star often rocked simple floor-length gowns in neutral colors, wearing statement pieces less frequently. And the Met Gala, also known as the fashion event of the year, was no exception. In 2008, Roberts attended the gala alongside designer Giorgio Armani, and for the occasion, she was dressed in a sparkly taupe dress, which was still simple enough to feel authentic on the star.

We've already seen that Julia Roberts popularized oversized pantsuits back in the early '90s, but in the early 2010s, the "Eat Pray Love" star was all about a more tailored approach to the boss-lady staple. In her mid-40s, Roberts appreciated the power of a cinched waist and sleeves that weren't way too long, as the star rocked a couple of classic pantsuits for industry events. Pairing her tailored pieces with delicate blouses or brightly colored button-ups, Roberts quickly became known for the powerful look.

Since the early '90s, it was clear that while Julia Roberts loved having fun with fashion, she wasn't among those who felt that beauty equals pain. Roberts seemed to prefer comfort, and every now and then, that meant ditching the high heels, even at high-profile events. In 2016, the star attended the annual Cannes Film Festival, and while she showed up to the red carpet in heels, she took them off before the stairs and walked the rest of the carpet barefoot. Heels or not, Roberts looked as stunning as ever!

Julia Roberts has always been the epitome of cool-girl fashion, but one thing nobody can deny is that her style only got better with age. As she turned 50 in 2017, the actor continued exploring trends, rocking pieces we hadn't seen her in before, from polka-dotted tights to sparkly jumpsuits. The star wore the latter in 2019 to The Fashion Awards, which she attended alongside her longtime friend, designer Giorgio Armani.

The early 2020s were marked by perhaps Julia Roberts' boldest fashion to date. Over the years, the "Ticket to Paradise" star has given us a plethora of interesting fashion looks, but the first half of the 2020s was marked by plenty of fun layers, unique silhouettes, and unusual textures. Of course, the fashion industry had come a long way in the previous decades as well, and Roberts knew how to make the trends her own. 

In her late 50s, Julia Roberts is more confident and stylish than ever. The actor has been in the spotlight through various stages of her life, from dating Hollywood heartthrobs to becoming a mother. With each new stage she entered, her style shifted ever so slightly, and in 2026, it's clear that Roberts has a great sense of what she likes and what she doesn't. She attended the Golden Globes that year in a deep cut black gown by Giorgio Armani, showcasing that fashion is a game she still knows how to play.