Sienna Miller: Style Evolution

Sienna Miller Style Evolution Boots

Boot Brigade

Who knows who started the boots-with-dress look? (And who cares?) But no question, Miller was at the forefront of making the look hot again. “She’s got guts and she’s always ahead of the times,” Bloch says. Not everyone can pull it off: this is strictly for 20-somethings, Bloch says. “You can get away with risky looks that would look too costumey on an older woman,” he says.

How to wear it without looking moronic? Do it Miller-style: Her ankle boots are a suede-y fabric that’s in sync with the hippie vibe of her dress. The boots are also a neutral color so they don’t draw in too much attention, which makes it fresh, not clunky. Oh yeah — having awesome legs is a must.