This combination of a denim jacket and a white long sleeve shirt is great for off-duty situations. Rounding off with a pair of black leather brogue boots is a simple way to introduce a little flair to this outfit. So as you can see, it's a dapper, not to mention season-appropriate, outfit to keep in your transitional collection. Wondering how to dress appropriately for your age as you slip into your 50s? This outfit is the perfect answer.