You'll be amazed at how easy it is for any guy to get dressed like this. Just a parka and charcoal wool dress pants. For a smarter vibe, why not add a pair of chelsea boots to the mix? As you can see, it's very easy to look dapper and stay toasty come colder days, all thanks to combos like this one. This getup illustrates that as a guy over 50, you still have a vast array of styling options.