A light blue denim jacket looks especially elegant when combined with brown wool dress pants for an outfit worthy of a perfect dandy. Complement this getup with brown leather casual boots to effortlessly amp up the street cred of your getup. While it can be a bit of a juggling act to stay fashionable on extra cold days, it's getups like this that prove it's quite doable. If you're not sure how to dress your age without giving up on style, this outfit is a perfect example.