Wondering how to wear ankle booties? Take note from the always cool Michelle Williams. By keeping the booties paired with a simple Alexander Wang sheath, she put both the shoes and dress in the spotlight. The soft drape of the dress and silver bangles keeps the look from going too tough.

Her makeup is also very natural and beautiful. We love the rosy cheeks and the subtly stained lip! Very on point for this season's makeup trends. So glad we saw some more Michelle sooner rather than later!

• Walter Steiger booties, $525
• Alexander Wang dress, La Garconne, $475