Before she was the 26-year-old blond movie star collecting her best-actress Oscar in her bubblegum-pink Ralph Lauren, one of the youngest in history to receive that statuette, Gwyneth Paltrow was a brunette school girl best known for being the daughter of Tony Award-winning actor Blythe Danner.

After making her screen debut as a teenager, it was a few years before Paltrow broke out with David Fincher’s Seven. Then came a high-profile relationship with co-star Brad Pitt, memorable performances in Emma, Sliding Doors, and Great Expectations, and her rise as a ’90s fashion icon.

Throughout that era and beyond, her tousled bob has been as obsessed over as her supremely casual red-carpet wardrobe, which ranged from effortless slip dresses and leopard-print coats to jeans, leather jackets, perfect white T-shirts, chunky knits, and Converse. And when she did go all out—in, say, a red velvet Tom Ford for Gucci tux for the 1996 VMAs, or in a knock-out Armani naked dress for the 1998 premiere of Shakespeare in Love? Well, then fashion history was made.

In honor of the Hollywood stalwart’s 53rd birthday, we present 33 stunning throwback photos from the first phase of Paltrow’s career—also featuring the likes of Kate Moss, Winona Ryder, Giorgio Armani, Liv Tyler, Leonardo DiCaprio, and Ben Affleck, as well as endless style inspiration.