REI

Trek women’s advocate Kate Nolan has ridden Town Run for 20 years. “It’s very flowy. There are lots of short step-ups and -downs, and I love the drops,” she says. “It has plenty of terrain changes, from hilly and windy to dirt berms in the prairie.”

“I kind of embrace the American workwear look. I like clothes that are classic and cool … sharp and comfortable. I like American workwear because it’s built to last, and it also ages beautifully.”

Surprise her with a hard-to-find down-filled skirt for winter walks or the slopes.