What to Know About Hiking ShoesBreak-inAll hiking shoes need to be broken in. KEEN Headout Waterproof All Terrain Hiking Shoes $135 at AmazonInsoleYour foot rests atop this cushion inside of your boot. How to Find the Perfect Hiking Shoe FitNow that you're well-versed in hiking shoe lingo, it's time to buy. Your hiking shoes should be a half size or full size larger than what you’d normally wear around town. Always break in new hiking shoes before your first hiking trip with them.