One thing I have learned during my time here in Chicago: there are some winter-wear items that you can splurge on, some you can just can simply scrimp on, and others that are best to deal-hunt for. I have learned this the hard way over the last ten years; being raised in Florida, I really had to just figure things out by trial and error.
Splurge: When it's 6am and you're waiting for the train for 20 minutes in 10 degree weather (without windchill), the only thing you desperately need is an extremely heavy winter coat. Because of their [high] prices, I have tried to scrimp on down coats for around $100 at Marshalls or TJ Maxx, but I find that the small details really make a difference. For example: a hoodie that is too light to stay up by itself in the wind or pockets that are not lined. And, because they're cheap, they only last two seasons before they are too worn to use. While some brands like NorthFace and Columbia, are more expensive, to me they are WORTH it for Chicago winters. This weekend Santa bought me the NorthFace Arctic Parka. This baby should last me at least 4 - 5 seasons.
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.
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