Hilary Swank Style Evolution

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Hilary Swank - Style Evolution

Check out how Hilary Swank's style has evolved over the years.

ADC / Rex USA

Hilary Swank - Style Evolution

Excuse us. Our mind just exploded. Who knew Swank -- sporting bouncy waves and a preppy kilt -- guest-starred on "Growing Pains" with a baby-faced Leonardo DiCaprio (and, oh yeah, that dude who played Ben)?

Hilary Swank - Style Evolution

Take that, Macchio! Boasting brown bangs and some kick-butt gray leggings, a 22-year-old Swank lent the "Karate Kid" franchise some girl power.

Hilary Swank - Style Evolution

A floral dress? Penny loafers? Was a fresh-faced Swank -- rocking a simple bob at a Hollywood Star ceremony -- already raiding future co-star Chloë Sevigny's closet?

Hilary Swank - Style Evolution

The high-waisted jeans and bangs say "Mom," the midriff-baring wrap top says "1,000 stomach crunches a day." Swank and leather-clad ex Chad Lowe went casual for the premiere of "The Long Kiss Goodnight."

Hilary Swank - Style Evolution

Face-framing layers and a red chinoiserie dress helped Swank get into character as single mom/Steve Sanders's love interest Carly Reynolds on the eighth season of "Beverly Hills, 90210," aka the closest Ian Ziering will ever get to an Oscar.

Hilary Swank - Style Evolution

Look -- a boa! This clean-cut "Cabaret"-style portrait was shockingly taken just a year before Swank's "Boys Don't Cry" transformation.

Hilary Swank - Style Evolution

In her groundbreaking portrayal of Brandon Teena in "Boys Don't Cry," Swank sported a masculine haircut, plaid button-downs, and jeans.

Hilary Swank - Style Evolution

Swank nabbed her first Best Actress Oscar (for "Boys Don't Cry") in a voluminous bronze silk Randolph Duke gown, Asprey & Gerrard diamonds, and a Jane Fonda-inspired layered pixie.

Hilary Swank - Style Evolution

All that boob-binding for "Boys Don't Cry" seems to have had a strange effect on Swank's chest. The actress hit the L.A. premiere of "The Gift" wrapped in silky gold pants, a frilly handbag, and a plunging cami that barely contained her "presents."

Hilary Swank - Style Evolution

Très belle! For "The Affair of the Necklace," Swank stunned in a frilly blue period costume paired with an elaborate bonnet over her curly wig.

Hilary Swank - Style Evolution

She may have been fired from "Beverly Hills, 90210," but two Oscars later, Hilary Swank is most certainly having the last laugh. And with her new film "Conviction" opening in theaters on Oct. 15, the actress's star continues to rise.

Read on as we trace the Elle November cover girl's journey from fresh-faced teen queen to androgynous "Boys Don't Cry" breakout star to bona fide Hollywood leading lady -- with a wardrobe to match!

And click here to check out Hilary's 10 best looks.

Plus, check out Diane Lane's style evolution.

Hilary Swank - Style Evolution

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