I used to have a shoe mountain but I hardly wore any of them as I had my favourites. I suggest you whittle down your shoes so that you have just your favourites and everything else can be donated/sold. I like to wear shoes that are comfortable and stylish and suit my personality. Knowing yourself is key. I have never been a fan of high fashion and high fashion only suits if it suits you. Be brave and wear what makes you feel good. The word comfortable sounds boring but why wear shoes all day that hurt?