“Pair simple leggings with a big sweater and flat boots or flat ballet type shoes. Keep it simple and don’t forget to add a few accessories to pull it all together.” — McGary

“Right now, I wear my leggings with an oversized button down shirt and a pair of moccasins. You could also wear this outfit with heels. The trick to finding a good oversized button down shirt is to buy one in the boys department, not the men’s. This way the shoulders aren’t so wide, but you still get that billowy effect.” — Finney

“I like leggings with an oversized V-neck tee under a fun cropped blazer with great heels.” — McDonald