John Shearer/Invision for the Television Academy
Andrea Cheng
Oct 01, 2014 @ 10:34 am

Lena Dunham’s new book, Not That Kind of Girl ($17; amazon.com), may teach life lessons, but it's her string of high-impact style moments that serve as a study in taking risks. If there's one thing the Girls star is known for, it's her unwavering resolve to push boundaries, from unabashedly clocking in (a lot) of nudity on screen to playing the red carpet wild card off screen. And how refreshingly so.

RELATED: Katherine Schwarzenegger: 8 Life Lessons I Learned From Lena Dunham's New Book, Not That Kind of Girl

For someone who's relatively new to the scene (Girls aired only two years ago), Dunham quickly found her stride and has since acquired a full roster of extremely memorable looks. Most recently, she shook things up at the 2014 Emmy Awards. Amid the usual parade of sparkly stunners and conservative gowns, Dunham's was easily the most polarizing—she ruffled feathers in an extravagant Giambattista Valli couture design (affectionately and infamously known as "the cupcake dress") that boasted a pale pink pajama-inspired top tucked into a tiered ombre skirt (above).

With a reputation of sartorial unpredictability, Dunham always has us on our toes. So with that said, we dug into our archives and compiled 13 of her best style moments, from her first Emmy Awards appearance to the present.

PHOTOS: Lena Dunham's Best Style Moments

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