At a certain point in a man’s life, most likely as the big 3-0 begins to loom on the horizon, he should probably come to the realization that he can no longer get away with always dressing as if he were back in college on a couch watching football at the frat. This is especially true when escorting his lady for a night on the town or even to the movies. If you are looking like this…

Nice look, K-Fed.

And your lady is looking like this…

Ooh la la, Malin!

You are courting an irreparable style gap and you better reconsider your threads. Y’see when a woman goes to all that effort to make herself lovely, she is going to expect a little effort in return. Particularly as she gets a little older (and you do, too) she is going to start looking around and seeing all sorts of well-dressed and successful gents and wonder why it is you look like a refugee from ‘N Sync circa 2000.

You’ve come a long way, Mr. Timberlake.

It’s a matter of basic respect. When I see a couple out on a date and the woman is dressed nicely and the guy has got on sweats and a backward ball cap I think Wow, dude, make a little effort, as well as That is never going to last. Think about the conceit it takes to believe that you have to put zero effort into your appearance and your lady is still going to find you attractive over the long haul. Put simply, that sort of laziness may fly in your 20s but it rapidly loses its charms as you get older.

But fear not. It’s really not very hard to get yourself looking good without going the “full dandy”. Continue reading →