A black polo neck sweater and white chinos are essential in any modern gentleman's smart wardrobe. Black leather double monks will breathe a dash of elegance into an otherwise mostly dressed-down outfit. So as you can see here, it's a seriously stylish, not to mention season-appropriate, combo to have in your transeasonal wardrobe. That's the style for a 30-something Millennial man to project you've got what it takes to succeed.