Feel free to check our fit guide and sizing video! As you first pull on your boots, they may feel tight until your heel slips fully into position with a satisfying "thump." The leather should feel snug around the widest part of your foot and on top of your arch, but not painful. This area will stretch with wear. Your toes should fit comfortably. If your toes are cramped, considering going up a half size. It is normal for your heel to slip up to a half inch at first. Over time, the leather heel counter will conform to your heel shape and this slippage will reduce. Ultimately, personal preference rules the day.