mens-fashion

Why I’ve (slowly and modestly) paid more attention to fashion for professional gain

Even in high school, I had it in my head that buying new clothes was vain.

Picture my mother pleading with me to let her buy me pants that fit me. At some point I realized that she had started sneaking in new pairs of socks and throwing out my old ones with holes. One of the first places I went after I got my driver’s license was to a thrift store, afterward proudly showing my parents a $5 suit I bought (and wore way later into life than I should have, like at our closing party at Philly Tech Week 2012).

While my teenage friends cared about clothes, I was defiantly disinterested in any of it. I was proud I saved what money I earned and perhaps prouder of how little I ever asked my parents to contribute. (For their part, they were more often embarrassed of my taking hand-me-downs from bosses and friends. They were worried it might look like they weren’t taking care of me, even though they most certainly were. I had one of the most loving households I could imagine, which might be why I didn’t want to ask them for anything else — look at how they helped me pay for college.)

But then I got older and entered the workforce, where the first impressions you make aren’t cast aside by the whims of youthfulness.

It took quite a few experiences as a professional for me realize that there’s a balance between spending too much money and time on clothes and too little, and I hadn’t found it. That’s when I had to make a change.

A pair of prominent examples:

  • For one, there was the time in spring 2009 that I noticed I had a hole in the crotch of my dress slacks right before I started a meeting with our largest Technical.ly sponsor at the time, whom I was meeting in person for just the third time.
  • In early 2010, I met with a trio of executives I was pitching on working together and later they told me they noticed the worn t-shirt beneath my ill-fitting dress shirt.

In 2011 and even into 2012, I did some of my first purging of old clothes as an adult, but I still was uncomfortable spending anything on a wardrobe. All I added to my closet was what I might receive as a gift, get as a hand-me-downs or buy at a thrift store.

But by the end of 2012, as I was leaving my mid-20s, I starting finally feeling my choices were become more embarrassing than a point of pride. I made jokes about my clothes with less gusto. It was a quality trait with which I didn’t identify anymore, a telling part of growing up.

I had crossed from financially conscious teenager into feeling and looking desperate. At a time when I was trying to make a small website into a small business, that wasn’t helping.

I credit my cofounder Brian James Kirk, who was rapidly growing his interest in fashion over those years, and my always supportive girlfriend at the time SACM, for helping me push through and kindly remind me I could loosen up my wallet a bit.You wear the clothes, they don’t wear you, as SACM would tell me. Buying clothes that fit me didn’t have to be vain or wasteful. It could be a professional and personal investment.

In 2013, one of my resolutions was to take a slew of modest steps forward into even the most rudimentary signs of modern style for a young professional. I bought my first new suit. I paid for a haircut (I hadn’t had a professional haircut since I was 15). I bought my first pair of shoes since I got a pair of sneakers with a gift certificate in 2010 — seriously.

Since then, I continue to get a monthly haircut — admittedly still at a discount teaching school. In 2014, I gave myself a budget of just a few hundred dollars to spend, and I duplicated that in 2015. I’m still slowly turning over my old wardrobe into something a bit more fashionable and, more importantly, stuff that fits.

I got those suits I bought in 2013 more modernly tailored. All told, between purchase and tailoring, the suits cost me just $500 each, and they’re relatively high-quality. I have three pairs of jeans, and I take care of them. I’m adding dress shirts that are slender and modern. I gave away nearly 50 t-shirts (most to make a t-shirt quilt) that were tied to good memories and kept only the ones that were the highest quality, comfortable and ones I liked. I bought business casual clothes that I liked and fit me well. Last year, I wore a tie that matched a pocket square, and I’ve gotten into buying colorful, comfy and overly-patterned dress socks.

For most of 2014, I was approached by people who complimented me on losing weight — I hadn’t. It was just the first time they had ever seen me wearing clothes that fit me.

Now, when I do still occasionally wear something that doesn’t fit correctly (that hand-me-down dress shirt with the too-baggy arms), I feel it. I better understand now what doesn’t look or feel right. I’m conscious of where I want my waist line to be. I took a pair of dress shirts I bought at a thrift store to get tailored, making something old into something new. There’s a balance.

For years, the idea of popular and attainable men’s fashion has been a growing trend for the retail industry, so I’ve taken a very limited hold.

The truth is that I always rather liked the idea that no matter how poorly dressed I was, I could always rest assured that I never spent more than the cost of a fast food dinner on what I was wearing. Don’t look at the clothes, take me for the value I have as a person.There was power in that, but I was ready for a new challenge.

Opening up a slightly larger budget, but still finding a way to feel comfortable and look current, has become a new goal and different kind of balance. I still spend less than many but I now care more than others. I do care about myself and how I look, and I hope it helps others around me feel comfortable putting their trust in me.

That’s why this can be important.

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