You'll be surprised at how easy it is for any gentleman to throw together this casual outfit. Just a grey wool long sleeve shirt worn with navy jeans. A pair of dark brown suede chelsea boots effortlessly dials up the style factor of your look. As you can see here, it's extremely easy to look on-trend and stay cozy when chillier weather arrives, thanks to this getup. Guys who are curious how to wear smart outfits as you make your way through your 20s, this getup should answer your question.