The absolute best part of being at the top of your game? Looking like it. The casually successful man too often relies on wearing what everyone else is wearing — a mixture of hunting clothes, fleeces, dad jeans, LL Bean “comfort mocs” and ball caps — in an effort to look like he has nothing but leisure time.
As Lyle Lovett said about some men’s dressing down: “It’s Saturday and I don’t care how I look, and I don’t care what you think of how I look, and I don’t care if I ever have sex again.” (Read more: Esquire: September 2013 – Esquire)
So gentlemen, you’ve made it. Keep setting the standard for those poor mortals who are still striving. When you drop the top on that vintage SL, look the part. Pair a patterned sportcoat with your (un-logoed) polo and some interesting shoes (like AE’s blue suede penny loafers above.) Come in to look at some casual fabrics for an off-duty suit or sportcoat. Think lightweight flannels and tweeds. You’ll look more put together, even in your dad jeans.
