Who said you can't make a fashionable statement with a casual ensemble? Turn every head in the proximity in a windbreaker and navy jeans. If you need to instantly dress up this look with a pair of shoes, why not complete this getup with a pair of dark brown desert boots? These picks will keep you toasty and stylish in transitional weather. Gents wondering how to dress well as you work your way through your 20s, you have your answer.