Hi, Will. Hope everything is well in Good Enough Guy land. Things are O.K. here. I feel very small for mentioning this and writing about it seems smaller still, but here goes. My husband dresses like an old man. He is wearing clothes that I think make him look like he should be someone’s crazy uncle and maybe people think he is mine. I don’t know. We are both only 44 and I don’t know how to tell him to be just a little “hipper.” I’m enjoying my youth and don’t want to be reminded of the future by looking at this man who is growing old gracefully, but dresses like he’s getting there way too fast. How do I convince him to dress his age? Help!

Out with the Outdated Outfits

Hey O.O.O,

Well the very first thing you should do is sit down and write to somebody else. Write to GEM or maybe my wife… ANYBODY BUT ME! I’m terrible when it comes to fashion. All I know for sure is that I don’t understand any of it. I don’t know the difference between dressing up and dressing down. Hell, from what my wife says, I can barely dress myself at all! For me, if it’s clean, and it still fits, I will put it on. And I don’t understand ANY of the fashion lingo. I thought an argyle was one of those winged statues that protects castles and I’m pretty sure a metro-sexual is someone who sleeps with cities. So I asked a bunch of my male friends and found out that most of us are clueless, which means solving this problem is easy! Here’s all you need to do:

THE COMFORT ZONE: As I said, I don’t know jack about fashion, but I do know the some basic rules that men live by and here’s one:


Sure, when we’re younger we may follow the trends and styles of the day (although you couldn’t have gotten me in a pair of skinny jeans at gun point), and in our late 20’s and early 30’s, we like to think we’ve developed our own “look” that sets us apart from everyone else. But somewhere around 40, a lot of men discover “leisure wear”; clothes that are made to feel good, instead of look good. We find out that the pants on the rack in the very back of the store have hidden elastic in the waist that stretches a little when we sit and stretches more when we eat a big meal. We learn that, as ugly as polyester is, it gives – and forgives – when we need it to. We figure out that those deck shoes that our dads used to wear slide on without a shoe horn, and no strings mean they never have to be tied, untied, or re-tied. And if no one steps in, we’re only a few steps away from believing that black socks, house slippers, and boxer shorts is an appropriate outfit for cutting the grass or washing the car.

FIGHT THE LAW WITH A LAW: Before you think that all is lost, there’s a pretty simple fix here because of another rule we men live by:


In most cases this law trumps the comfort law simply because, to men, attraction might mean sex, and sex is better than comfort.

Buy your guy a couple of new outfits “just to try” and then really make a fuss over how drop-dead sexy he looks in them. Tell him how much better his butt looks in those new jeans, or how you’d forgotten how great his arms looked in short-sleeved, silk, shirts. Tell him the black shirt and tie make him look one of those hot, young, vampires from whatever show and so on. Hell, I’ve got a friend who is convinced he looks amazing in cowboy boots and a sleeveless T-shirt. How did he come to believe that? Take a guess.

Of course we must assume that, eventually, a man may reach some age after which the pursuit of sex would be less important than the pursuit of comfortable clothes.I pondered the specifics of this question during one of my discussions, and none of my friends had any idea what age that might be, so I went to that well from which most of my knowledge springs: my father. That’s right. I called home and asked my 75 year-old dad at what age is sex really not that important any more.  His reply: “Son, you’ll have to call and ask someone older than me.”

Anyway, good luck to you and your hubby. I’m sure you’ll get this one ironed out.

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Male Cleavage: When’s It Time To Cover Up?

The GEM Debate: Should You Be Fined For Wearing Saggy Pants?

The GEM Debate: Can You Wear A Mini-Skirt After 35?

William Jones is originally from the tiny town of Alton, Illinois, and now lives in the tinier town of Reisterstown, Maryland. He is a happy husband and a proud father of three, and writes as a hobby, in those few moments he finds between husbanding and daddy-ing. Follow him on Twitter @goodenoughguy1.