For an outfit that's city-style-worthy and effortlessly sophisticated, choose a grey plaid wool waistcoat and white corduroy chinos. So as you can see, it's very easy to look awesome and stay warm when chillier weather arrives, all thanks to outfits like this. As a 30-something gent, you want to start dressing more professionally. If that's the case, ensembles like this are a foolproof option.