Shootingstar, I hear you about the sticker shock on these more fashionable winter boots you're looking for. I have a process that helps me rationalize the more 'spendy' purchases:

- can I make the item myself?
- what purpose does it really serve for me to own this item? how long will it last? do I feel like I will get good value for the life of the item?
- where/how was it made? do I feel reasonably assured that the people who made the item, from design through production, earn a reasonable wage? same questions about the retailer -- are they compensating their employees well, do profits stay in the community or do they go to a corporate HQ far away?
- are there other ethical considerations involved in the manufacture of this product would incent/disincent me to buy it?

At the end of the day, I may waffle on plunking down the money, but I have rarely regretted it once I decide to bite the bullet. If I buy a quality item that lasts for a long time, that actually may be cheaper in the long run, as opposed to buying "disposable" items that need to be replaced more often.