Steal a Deal: For the 50-degree days and for nicer occassions, you'll need a coat that's not so utilitarian; I've found that I like wool trench coats or peacoats. Though they're less heavy than the down coats and parkas, they should still be lined. I refuse to purchase any coat that does not have pockets (why even make such a ridiculous product?) and I like this item to be in a color or a camel/tan base, so that it will match with either black or brown outfits. The department stores can charge $200+ for these items; I almost always buy mine at Marshalls or online. This year I purchased the coat below, in Avocado, from Overstock.com with a 10% off coupon for $75.
Scrimp: While I love name brands as much as the next person, I have found that some items just take too much of a beating during the Chicago winters to really be worth the purchase. For warm boots of a certain will-go-unnamed-but-very-popular-brand, the salt and mush just tear up their fabric and make them quite unsightly by the end of the season. So, instead of buying $170 *** Boots every winter, I've opted to buy a less expensive brand this year. These boots have rubber soles (unlike *** brand), warm lining, and are super comfortable on frigid days. At only $30, if they don't last more than one season, I don't really care!*
*Note: for serious snow boots, I have found that the study ski boots I bought for $170 have served me amazingly! I am still able to pull them out three years later when those serious snow storms come through.