For laid-back elegance with an alpha male spin, rock a white vertical striped dress shirt with light blue jeans. Not sure how to finish off your getup? Wear a pair of dark brown leather tassel loafers to turn up the fashion factor. Can you see how extremely easy it is to look dapper and stay warm when chillier weather arrives, all thanks to looks like this? Wearing this, any over-40 man is bound to put any younger dude to shame.