Anna Wintour Bob-o-lution

Defying the big-hair trend with her sleek and chic bob, Vogue's newly appointed editor-in-chief was rather regal at the "From Queen to Empress" Costume Exhibit.

Anna Wintour Bob-o-lution

Swing out, sister! The London native sported a shorter, sassier cut at the Fashion Group International's Night of 100 Stars.

Anna Wintour Bob-o-lution

With her glam bob snipped into a slightly '70s style, Wintour skated into Dorothy Hamill territory.

Anna Wintour Bob-o-lution

Glossy locks and a sheer top seemingly swiped from a supermodel had the on-trend editor looking like she belonged in the pages of Vogue.

Anna Wintour Bob-o-lution

Wintour took a fashion risk with her gold lame shirt, teal skirt, and chunky gold accessories, but played it safe with her always classic bob.

Anna Wintour Bob-o-lution

At the Fashion Group International's Night of 100 Stars, Wintour made like a '30s silver-screen siren in her elegant blunt cut, white dress, and multistranded necklace.

Anna Wintour Bob-o-lution

Looking lovely in lavender, Wintour modeled the exact same style that would one day be stolen by Suri Cruise.

Anna Wintour Bob-o-lution

The couture queen rocked streaky strands – and an equally streaky stole -- at the 2002 VH1/Vogue Fashion Awards.

Anna Wintour Bob-o-lution

Well, look at hue! With a red, red, noggin Wintour went bob-bob-bobbing along.

Anna Wintour Bob-o-lution

Blonded, blue-jeaned, and bound in leather, Wintour was the coolest mom ever as she accompanied daughter Bee to Marc Jacobs's Fall Fashion Week runway show.

Anna Wintour Bob-o-lution