As stated above - to break the gillie's in - you have to wear them. Saturate the leather with neatsfoot oil to start softening the leather. I would put band-aids on my heels (or tape) knowing blisters are possible. Also, an old shoe salesman told me if your shoes are a 1/4 size too large, put an insole in them (a second if there's already one) to bring your foot up tighter in the shoe. I'm heading out to a black-tie Burns-night (belated due to COVID) tonight so luckily mine are about 5 years old and comfy.