The boho skirt is making a comeback this fall—thinking of swapping out that undulating, maybe crocheted, maybe swirling-patterned skirt in favor of the textbook, cooler weather-ready wool number?

In New York, these sporty-chill trousers have remained a staple wherever fashion-conscious people dress comfortably: bodega runs, dog walks, Terminal 4 at JFK. But women in Madrid were low-key styling ...