Spotting an Olsen twin on the street is like catching sight of a shooting star—rare and enchanting. So, I’m considering this a lucky week, as we just got our first sighting of Ashley Olsen in months.

There’s something about a wide-leg pant that’s just effortlessly cool. Maybe it’s the way they swish when you walk, commanding attention without trying too hard. Or maybe it’s just the fact that they ...