If jeans are okay, it definitely makes it easier for those days when gear boots are really the only option. The way I see it, if you're there for the long haul, then boot buying is a marathon --- over time, if you buy quality, you'll amass a wardrobe of boots and coats, because it just plain makes sense. But because these tend to be the priciest items in the wardrobe, it really does take patience. I've been on YLF since 2010 (I think?) and building a wardrobe since then, and even now I feel like I could use another pair or two of boots and another coat or two! My winter is anywhere from 5 to 6 months, though, and -- on a positive note -- most coats and boots have serious wardrobe longevity, so while expensive, you will have them and feel stylish in them for years (assuming you don't wear them out.) The more pairs or items you have, the longer it will take to wear them out. This is why I've slowly but surely been adding to my quotient.
Also -- although it makes me crazy sometimes, I try to "listen" to the weather. If you like to vary your silhouettes, that will be a good thing and a bad thing. You'll enjoy changing things up when the weather cooperates, and feel annoyed if the weather holds in one pattern for too long. I get really bored in winter when I am restricted to tucking into my boots for weeks on end...and yes, wide legs are really tough to wear except in fall, really. Sob!!
A wintery boot with a slight heel can be really great with dresses; I wear the black block heeled semi-equestrienne style with dresses and wide leg crops/ culottes and they work great. They're narrow on the ankle so that gives structure, vs. the flat riding boot which has a different shape.
To give you an idea...my two tall La Canadienne boots are now five years old and still look basically new -- I don't wear the dressiest one often but am glad it is in my arsenal and I wear the other one (with the block heel) a ton.
Blundstones are 3 years old -- about done because I wear my footwear hard on the heels and they're not really candidates for resoling.
Adirondacks also 3 years old and still like new...
Short Aquatalias, Eccos, and Merrells are from last year. (Aquatalias got hit by very bad weather conditions and I will need to replace next year.)
Tall Aquatalias and short LaCanadiennes are new this year.
I spend a lot on my footwear -- but if you stagger your buying, adding one pair a year, say, or maybe two, you'll soon end up with a collection. Ditto for coats. Look for end of season sales, maybe..