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.
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!











I think one of the biggest struggles parents face is coming to grips that there is life outside the home and that we become disconnected from it when we have little ones. The other struggle for us Gen X'ers is that you either dress like a kid or a corporate suit and that it seems like there's very little in between that defines “age appropriate” for us.
I've never had any sense of style. It made the transition to parenthood that much easier
Good point, Dave. I know you in person and know that you have always dressed well but you hit it on the head – how do I dress my age and still wear what I like? The balding thing cannot be underestimated, too – I'll write more on that topic. I don't mind being bald at all, but it changes the whole symmetry of your face. And when bald guys dress too “young,” they really look desperate and out of it!
Since you asked for my thoughts, how could I not comment… So exciting, like I have my own fashion column…
First, here's where I think you're crazy… I agree that you don't want to dress like you're in high school, but the wingtips, the tweed coat, the knit tie and the outfit above, all totally appropriate on you. You wear a well cut tweed jacket, some inky blue jeans and brown wingtips to work and if nobody tells you that you look good, i'll pay for the outfit
Pleats are a mess. If you want to look 20 pounds heavier, then get yourself some pleated pants. As for the low cut pants, blame Versace for starting the trend, but think of it as the same evolution that women's jeans underwent when mom jeans finally began to die out. If they're too long, $10 gets them hemmed.
Tailoring – everyone should buy half as many shirts and spend $15 extra on each to have the sides taken in. American men's shirts are cut like a box because that's how most American men are built. If you're not and you wear a boxy shirt, there’s another 20 pounds on your look again.
Footwear – who was this metro co-worker? Me? Daniel? Whoever it was, he was right. A pair of $18 rubber soled shoes will make any outfit look ridiculous. A decent pair of black and a decent pair of brown will cover you 99% of the time.
And I have no problem with khakis, they just need to be the right khakis; a little skinny and no pleats. As long as the shoes are good, and you put a little effort into whatever's on top, you're good.
If anyone deserves a fashion column, Todd, it's you. All right, this is terrific advice. Answer to your question was it was Daniel. I should start a column called “ask the Style Guy” in which I ask you questions and you answer them.