Some things never go out of style. Little black dresses. Classic trench coats. Riding boots. And for Anna Wintour, The Bob.

The Vogue editrix has bowled over the fashion industry with her flapper-era follicles for years, the coif giving credence to the idiom, "If it ain't broke, don't fix it." Or, for that matter, cut it.

In 1990, Wintour sported a short, blunt, Louise Brooks-esque bob that landed just above her jawline and skimmed her killer cheekbones. With her boxy plaid blazer (it was the decade of excess, after all!), black top, and strands of pearls, she was a modern-day (well, '90s-era) Coco Chanel.

Fast forward 20 years and Wintour was the belle of the 2010 Met Ball in May, glowing in silvery white Chanel Couture and longer, lighter locks that proved to be her crowning glory.

And see who aptly rocked a bob on the latest cover of Vogue.