I was never a snappy dresser but I used to know how to put an outfit together. Recently I realized I’d forgotten how to dress myself and decided to do something about it.

J.Crew Herringbone vest. Taken from GearPatrol.com

I blame my wife for some of my missteps. Part of the reason I stopped knowing how to dress myself is because I stopped shopping for myself. Items of clothing I liked and with which I was comfortable seemed to go missing over time; new ones appeared in their place that my wife had acquired. This worked out fine when I wore exactly what missus told me to wear. Left alone, I was laughable. Worse, I earned the question, “What happened to that man I was so attracted to, the one that always used to wear such cute outfits?”

Part of the blame must also go to the kids. First of all, I was tired all the time, pouring myself into clothes in the morning so that coffee could be poured into me. But second, what was the point of wearing a decent shirt if it was just going to end the day having served as napkin, dish towel and snot-rag?

I ‘m being facetious – everyone should have a wife and kids like mine. Really, the blame for my couture is mine alone to bear. I’d gotten lazy about it. Today’s casual workplace and the nature of my work, which rarely involves face to face contact with clients in favor of emails and phone calls, has required little of me. So I simply decided it was a new day. Time to change clothes.

So what did happen to the man that impressed the girl who was to become his bride while wearing the overcoat and scarf? I had to reach back in my memory to a time when I enjoyed clothes and remember what it is I had liked and what had worked on me.

All my adolescent life and into my twenties I liked clothes, while never being much of a dandy. I especially loved classic looks that pre-dated me; suits, ties, tweed jackets, turtlenecks, vests. The truth of the matter is I had never spent much money on clothing. I had always haunted second-hand stores for my outfits and had pieced articles together with hand me downs from my dad and the occasional new piece. I had never had the experience that most American men and women seem to have had; attentive shopping at malls and such for new items and complete ranges of outfit options.

No, I was more often found in the same pair of jeans and rumpled shirts in conservative styles and colors and low-maintenance fabrics, wing tips or ankle boots from the 70s, sometimes paired with an unbuttoned vest, knit tie and the jacket from a men’s suit, often favoring the boxy cut of the late 60s. You’d find a lot of real gems in the Value Worlds and St. Vincent thrift stores of my youth – and this before there was much of a trend in what we today call vintage clothing.

So, no problem, right? Clearly it’s simply a matter of bringing these things back. What’s old is new again. Well, I don’t think it’s that easy. The outfits I just described worked on me then because they looked appropriately boyish. The guy that looks at me when I shave ain’t a kid. He’s bald, for one thing, a topic in itself, and I think he should look his age. The outfit shown above, for example, would look silly on him.

Happy ending is I’ve been looking better, even getting compliments on my wardrobe – sometimes even from my wife. But the truth is this is still a work in progress so expect more from me on this topic to come. For now, some preliminary findings:

-Pleats, they must go. At the same time, why do pants these days have to ride so low on the hips and drape so far over the feet?

-On that note, I know now the value of tailored items. I am no longer as slender as I once was – but I am, in fact, in the best shape of my life. Like most bodies, mine’s made up of unqeual parts. For shirts this means I have a bullish neck and short torso on a slender frame, making shirts look either too small or too blousy on me.

-Footwear. My 20-something metro co-worker told me once I had the elements of the outfit together but you cannot compromise on the footwear.

-Denim. It seems to me a nice pair of jeans goes with anything and makes whatever you’re putting together pop.

-Khakis. So ubiquitous, so easily undermined; so easy to take a pair of khakis and turn and outfit boring. How to avoid this?

To be continued!