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Ultra-casual in 2008—so different from the Old Hollywood styles she goes for now.

She ups her game a little with heels and jeans.

The California hippy look may have been Ashley's signature, but soon after this picture she retires it from the red carpet.

We really, really like this Dolce & Gabbana dress and it fits the actress perfectly. Her ascent begins.

Ashley began her entrée into the more stylish ranks in this curve-hugging L'Wren Scott number at the designer's Spring 2011 show. Love the color, love the fit. Love.

Beginning what would soon blossom into a fruitful partnership with the fashion house, Ashley wore jewel-toned Donna Karan to the designer's Spring 2011 show.

In one of her other favorite labels, D&G (R.I.P.), Ashley hit the red carpet at a Cinema Society screening of The Twilight Saga: New Moon. We love when she takes chances on more editorial looks like this one.

Now this is how you wear a casual look. Ashley looked laid-back but chic in leopard-spotted Giambattista Valli last November.

In another winning Donna Karan look, Ashley channeled Veronica Lake at an Avon Foundation event in NYC.

Getting back into the fashion show circuit, Ashley attended Salvatore Ferragamo's Resort 2012 presentation in a head-to-toe look from the label. We especially love that houndstooth clutch.

By 2011, designers couldn't get enough of Ashley. Here she is with Michael Kors (wearing his design, of course) at the CFDA Awards.

After wearing this stunning, sparkling Donna Karan gown at the 2011 Met Gala, Ashley officially entered fashion's major leagues.

Notice how Ash's off-duty style has gone from super-casual to effortlessly polished? All part of the transformation.

In one of her finest red carpet looks to date, Ashley wore this ruffled crimson Donna Karan number to the premiere of The Twilight Saga: Breaking Dawn - Part 1. Lovely.