Can you wear cropped jeans in the Winter? Yes! Here are my tips for those living in a cooler climate who want to keep their ankles warm! Wearing a medium in sweater! Comment SHOP for all links! Make sure the top of your boot is not SHORTER than the hem of your jeans! A Taller slim boot shaft that fits inside the leg is ideal If you want to wear loafers or sneakers, add a cute sock! I linked some great Cashmere Blend socks for $12! cropped jeans, how to style, denim, loafers, boots LTKStyleTip LTKstorytime LTKOver40