Hit the bit that goes over your achilles tendons with a hammer to soften if its boots. If its shoes hit the top of the back of the shoes. I had some new ones last year, shoes with metal studs on the toes & heels, love them but so uncomfortable to start with. A friend suggested weeing in them to soften, apparently this works very well but i'd never heard of it & didn't wantt to rust my studs so didn't attempt it.
well ive just bought a spray from Thompson shoe specialist ( as advised by Office-shoe shop girl) and sprayed my boots inside and outside ( where they hurt) and quickly put them on…why oh why didnt i know about this product before….ive had my boots for a year now and only last week they felt comfortable on…give it a go, best ever thing
I steamed mine over the kettle, put them on and stretched the back down by pushing my leg back, iykwim. I moisturised the leather afterwards, so the heat/steam wouldn't damage the leather, and they've been fine.