The avid gymnast and swimmer at South Pasadena High School sported poufy '80s bangs.
After chopping her locks for her breakout role in Boys Don't Cry, Swank rocked cinnamon extensions and baby doll makeup.
She picked up her first trophy (and embraced her grown-out pixie) at the Academy Awards.
The Affair of the Necklace lead highlighted her natural beauty at the Oscars with a face-framing angled bob and mauve shadow.
Swank got gorgeous with long honey layers and shiny peach gloss at the 90th Anniversary of Paramount Pictures bash.
For the L.A. premiere of The Core, Swank opted for a curvy, retro-inspired half updo.
A swept-back updo accented her diamond drop earrings at the Academy Awards.
For her second Academy Award win, Swank chose a sleek and understated low bun.
Lush ginger waves brought out her chestnut eyes for the MTV Movie Awards.
Long, swingy bangs and straight strands for the New York City premiere of The Black Dahlia.
The P.S. I Love You star played up her complexion with subtle shades. "Her skin is tight, and it glows," makeup artist Kara Yoshimoto Bua has said. "It's a great canvas."
The Birds of America beauty went short (and blond!) for Amelia-and Pantene Pro-V's Beautiful Lengths charity, which donates wigs to cancer patients.
Her stylized (but decidedly unfussy) curls were a new take on Old Hollywood waves.
Height in the crown equaled instant glamour for the Boss Black show in Berlin.
Soft pink lipstick and ombre highlights for an Italian film festival.
For the Costume Institute Gala, Swank channeled Veronica Lake with side-swept waves.
The actress stunned in Old Hollywood waves at the Vanity Fair Oscars party.
During Milan Fashion Week, Swank complemented her shimmering ensemble with soft waves and glossy lips.