Some tips on clothing

I live in a cold town. Not the people, just the weather. I think that if someone tried this Lenten sacrifice in a warmer city, it might be easier just because of the clothing choices. Every day I wear: two pairs of socks, long underwear bottoms, pants and two layers on top. I wear a coat/parka, scarf, a hat and gloves. I also carry ear covers, just in case it gets windy. The socks tend to be thinner so I can fit my feet into my shoes still. The long underwear is also thinner. I prefer Smartwool socks and Zimmerli long underwear. Both are really comfortable and I don't get ridiculously warm once back inside. Now shoes are another matter. I have been reduced to wearing my steel toed hiking boots or my leather clogs. This is for two reasons. 1) Wearing the boots makes walking through slush and snow a considerably warmer experience, not to mention a little less treacherous. 2) I made the mistake the first day of Lent of wearing my cute new boots and then walking home from Ash Wednesday services. Home is about 3 miles away from church. I had blisters like you wouldn't believe. Not having cute shoes is something I lament. I would love some tips on cute reliable warm shoes for walking in the winter.