We all have our favorite Julia Roberts style moments from the ’90s. There’s Julia as Anna Scott in Notting Hill uttering the inimitable words: “I’m just a girl, standing in front of a boy, asking him to love her,” while wearing a baby-blue cardigan. Then there’s Vivian Ward’s PVC knee-high boots in Pretty Woman, or the many wedding dresses of Maggie Carpenter, the ultimate Runaway Bride.
Off-screen, Roberts modeled some of the most memorable Giorgio Armani red-carpet looks of all time. Namely, the grey oversized trouser suit and tie she wore to pick up the Best Supporting Actress statuette for Steel Magnolias at the 1990 Golden Globes. Accessorized with tumbling curls and that megawatt smile, Roberts’s Annie Hall-esque tailoring is the stuff of Hollywood fashion folklore.
Remember her engagement to Kiefer Sutherland? The slouchy tailoring she wore on the arm of her actor beau at the start of the decade would fit seamlessly into the contemporary wardrobes of ’90s obsessed models like Bella Hadid and Kendall Jenner. So, too, her slip dresses, The Matrix-esque leather jackets and crop tops.
On her 55th birthday, here are 17 times Julia Roberts aced mannish blazers, waistcoats, strapless gowns and everything in between.