Denim and boot outfits. How to style jeans and boots. The key is to wear your jeans over your booties. Make sure your booties have a tall enough shaft. Gentle Herd coat xs (old) Velvet sweater small (old) Levi’s jeans 25. Cut hems. Madewell dimes booties 5.5 Little Liffner hobo bag in dark brown J.crew belt xs Celine sunglasses LTKSeasonal