Until recently, I did not know how to dress myself. Well, I exaggerate. I knew what clothes were, how to put them on, and could arrange my clothing as to go outside clad in a manner that was mostly weather appropriate and in tune with local decency laws, but that still left a lot of leeway. I don’t know why I never learned how to dress myself properly. It may have been the stringent uniforms of my early Catholic School education days that left me with a distaste for ties, dress shirts, and canary yellow that I’ve only recently gotten over—save for the canary yellow part. It might also have been the adolescent infatuation I had with the “goth” thing which lead to me wearing all black in a vain attempt to be rebellious and threatening. It could also be the transition from that into an equally apathetic college wardrobe of all black because I was lazy. I don’t know.

I do know that awareness of “proper dress” came to me about the time I was about to graduate college. Facing down the idea of job interviews and life as a working man, I realized that something had to change in my appearance. I posted a question on Ask MetaFilter asking for advice on dressing like an adult, but the answers lacked some of the more concrete details… So, as I graduated college, I went from being a long-haired, bearded, chubby dork who wore monochrome to a clueless, short-haired, clean-shaven dork, who wore bad outfits, cheap clothing and a rather pretentious, cheap black felt hat. Still, I think I was more ahead of the game than some of my peers who even now somehow manage sartorial disasters that blow my mind, or just look like schlubs, even today.

It was during my period of semi-unemployment that dressing correctly really came to my attention, thanks in part to the great blog Put This On, which taught me the basic rudiments of classic men’s style. With my limited income and access to some thrift stores and eBay, I began to toss out the ugly sateen shirts and beat-up cheap shoes that I had worn to my office job. Sure, I’d dressed well enough to get the job, but that job probably would have hired me even if I had come in with only the barest minimum of interview-appropriate attire. I needed to step up my game, not just for the job hunt, but for myself.

Fear of a White Shirt

For many years, the only whites in my wardrobe were my undershirts. No other white garments even existed in my wardrobe. No white socks, no white underpants, nothing. I wore a lot of black and gray, some reds and blues, and the occasional spot of brown when I felt flashy. I remember the first non black or gray item of clothing I picked out for myself: a short-sleeved brown button-down shirt. I still have it, but not for long. The majority of shirts in my wardrobe were polyester blends, ill-fitting, and often in dark shades. It lead to a bit of teasing at my old job whenever I sauntered in wearing a bright red shirt. [1] I decided to invest in something white, just as a first step. I secured a lovely Oxford Cloth Button Down—OCBD, in the style parlance—at my local thrift store. It was as good a fit as one can get from off the rack, and looked good paired with dark denim. It was a start. Until then, my “best” shirt was a garish blue number with French Cuffs. [2] Not long after I got the first of my OCBDs, I got a full weeks worth, some with pointed collars, some button-down, and explored a new world to me: patterns.

Pattern Recognition

I never liked strongly patterned clothing. Still don’t. Stripes and things were just too darn complicated for me. Keep in mind, my idea of varying my wardrobe until about a year prior was wearing gray shirts or blue jeans instead of black ones. As I’ve grown my wardrobe, I’ve started to get an idea of what goes with what, both in terms of color and in terms of pattern. One help has been the BeSpeak app for the iPhone. It gives suggestions based on items in your wardrobe and tips on what patterns and colors suit you. It mostly focuses on suits and ties, but it is still a great resource. I now wear striped shirts and patterned ties, and thanks to BeSpeak, can even match them properly.

Suiting Up

Early on, I had made the mistake of thinking I could fake a suit. I had purchased a nice enough gray blazer, and it matched well enough with a particular pair of gray slacks I had, but it wasn’t enough. I think people could tell that I was trying to fake it. One of the most important purchases I made, early in this project, was a lovely, gray herringbone wool Hickey Freeman suit. It was a bit long at the sleeves and legs, but it was perfect interview wear. I kept promising myself that I would get it altered, and eventually I did—over a year after the fact. [3] Now that I have it back, I only wish I had done it earlier—the fit is so improved it’s insane. I look good, and I feel good in it. After alterations, the gray suit cost me a mere $80, and looks incredible. It feels great to wear a real suit, and to look good doing it. Now, I just need to get the three-piece navy pinstripe suit I found to my tailor, and I’ll really be set.

Shoes and Perish

Douglas Adams wrote an amazing thing about cheap shoes—the Shoe Event Horizon—which states that as shoe demand increases, quality diminishes, causing people to buy more shoes of lesser quality, until at last the economy collapses. I didn’t have $200+ to spend on high quality shoes, but there’s a wonderful resale market on eBay for them. I picked up a pair of $250 Allan Edmonds shoes for $80, and with care, polishing, shoe trees, and occasional resoling, they’ll last me for life. I’ve bought a few other nice pairs of shoes this way, too. The only shoes I’ve bought new were a pair of city boots that, though not exactly fashionable, are at least well made and good for the cold, wet, urban winter. Now I have shoes for almost every occasion I would need, and don’t have to pray someone doesn’t realize I’m wearing boots.

Putting it all Together

I’m far from a fashion plate, and I certainly am not trying to be. I do, however, have the ability to dress myself now, in a way that is attractive, appropriate and functional for home, work, and play. I’ll never forget visiting my parents and the look of surprise on my father’s face when I appeared with a striped Oxford Cloth Button Down, a brown sweater, and looking quite nice. I look better, and I feel better, and that’s a huge boost to my self-esteem—as long as I don’t have to wear canary yellow.