I like to categorize everything I wear into two main parts. Cold weather clothes and warm weather clothes. Since it's cold here for most of the year I have a lot more cold weather clothes which I'm quite happy with since I enjoy that kind of clothing more.
In the winter/fall I tend to wear a lot of scarves. I have a bit of a scarf collection going on right now and I find that they go with just about any outfit, so I typically will wear one everyday during the colder months. Also I really love beanie hats and I've begun to incorporate those into my cold weather outfits, but I don't think I pull them off too well so I only wear them on snowy days since that gives me an excuse. As for shirts I usually always have an undershirt on no matter what the season. Then on top of that I may put on a nice cardigan, sweater, or one of those fabric buttoned up coats. Lately I've been thinking about getting a poncho, but only the really fashionable ones and not some wool mess or anything with crazy sparkles or designs on it. Then for pants I go with jeggings, leggings, or now jeans once in a while since I don't find them very comfortable anymore. As for shoes I do like Ugg boots, but I also have an assortment of other boots and moccasins of course!
In the warmer months I don't like dressing up as much because I find you can't use as many clothing accessories. Although I think you can get away with more jewelry since warm weather means thinner clothing and anything like a large necklace flows better and is more noticeable. As for clothing I'll wear mostly short sleeve shirts with some kind of pattern on it like flowers or whatnot. I do like three quarter length sleeves maybe more in the spring when it isn't as warm. I also try to go for bright colors in the summer and I can't forget button up plaid shirts! I tend to still wear the same kind of pants in the warmer weather just because I love them so much and I just don't care for shorts. For shoes I stick with flats mostly, but I do have sneakers if I go anywhere really outdoors like. I should also mention I love summer dresses, but I haven't had the opportunity to get one yet. Although I'll be mixing that in soon enough.