This combination of a shirt jacket and a short sleeve shirt can only be described as seriously stylish and casually classic. Inject a hint of sophistication into this ensemble by sporting a pair of dark brown leather tassel loafers. Can you see how super easy it is to look stylish and stay toasty when colder weather comes, all thanks to looks like this one? This outfit demonstrates that figuring out how to dress well at 40 and beyond is easier than one might think.