As popular as it may be among fashion connoisseurs, the fancy-sneaker outfit is easier conceptualized than pulled off. The underlying hitch: While we can easily imagine ourselves twirling around in some billowy, pleated skirt and Chuck Taylors as Bill Cunningham ever-so-casually snaps our pictures, we're ultimately wary of coming off like we're trying too hard. The mere notion of it is usually reason enough for us to switch back into ankle boots — or pants. But, not today, friends.
Today, we're tackling our sartorial fears head-on by assembling five sneaker-and-skirt combos to rival some of the best we spotted at Fashion Week. Whatever your flavor — maxi, midi, mini, full, pencil — we have all the clever styling tips and shoppable pieces you'll need to nail each outfit. Be sure to tell Bill we say "Hi".