This pairing of a navy houndstooth wool waistcoat and white dress pants embodies masculine sophistication. Don't know how to finish? Introduce black leather chelsea boots to this outfit to spice things up. Piecing together a standout combo can be a bit of a conundrum on its own. Enter below-freezing temps into the equation, and the whole thing becomes all the more difficult. Don't despair, this here is your wintry inspo. The ability to pull off ensembles like this is one of the advantages of going into your 30s.