The Unnecessary Pressure of Dressing Well

I used to put a lot of pressure on myself to dress well. I'm starting to relax both my attitude and the fit of my clothes.

I just changed my shirt because my sweatpants didn’t match the t-shirt I was wearing.

Even at home alone, on a Sunday morning, I noticed and it bothered me. Dressing well, it seems, is deeply embedded in my soul now.

Well, let’s not say well. Let’s say passably. I aim to dress passably. I’ve never claimed or desired to dress fashionably so let’s be clear on that up front so you don’t feel the need to eye-roll your way through this whole thing. Maybe at times I have looked fashionable. Maybe. But that’s not at all what we’re talking about here. The important thing to me was that no one would look at my clothes and go “WTF??”

And believe me, I have dressed in all manner of WTF over the years.

Looking back in anger

I moved to Montreal with only a suitcase full of my best clothes. It contained a sweater that made my head look tiny, a neon green dress shirt with a giant collar, and the shoes. Oh, fuck me, the shoes were bad. I wore a pair of horribly-unfashionable, square-toed, black, leather, slip-on shoes.

And yet those horrible black shoes were a significant upgrade for someone who thought training shoes were the everyday footwear of the entire world. A suit would go with nice shoes, sure, and boots for working messy jobs, but every other occasion? Reebok.

This was the norm, as I understood it. No one ever told me otherwise.

There was one other pair of shoes I brought to Montreal – white / grey casual shoes, the style of which I can only describe as “bowling shoes.” I remember a woman in a coffee shop in St. John’s commenting on them saying how nice they were. They were not, I know now, something any self-respecting man should have had on his feet, but I didn’t know that. I was just happy that I had finally graduated from the sneaker-people.

The only picture I could find of them. You get the idea.
The only picture I could find of them. You get the idea.

I clearly had to up my game. This was Montreal, after all. I had to look as stylish as I always thought this city was known for.

(I would later discover that you can wear a garbage bag shirt down the street in this town and no one would bat an eye. It’s a very “you-do-you” kinda city with more art than affluence and no pressure to fit in and I love that about it.)

Going to fashion school

I started doing research on male fashion. I found a helpful subreddit called Male Fashion Advice. I subscribed to GQ because I remembered a time years prior when a friend (probably trying to be helpful) sat me down and thumbed through a GQ with me. I remember I was wearing a black zip-up fleece sweater from MEC at the time which I thought looked rather good on me. I wore it everywhere … except anywhere it might have been intended for, like, say, hiking.

Anyway, I also spent a lot of time just looking. At people, at clothes, at the clothes on the people in the TV. I spent time in stores just going through the clothes and in particular the mannequins. I was trying to make sense of it all.

“That’s an interesting outfit, mannequin. What kind of person are you?” Then I would give them personalities. I can’t tell you how much I learned just by staring at plastic people. Watching through the video monitors, I’m sure more than a few mall security guards thought I was … special.

I was fortunate to have done enough web design that I understood some basic colour theory. Not that I was good at choosing colours, but I least I understood why a certain colour of pant would be matched with a certain colour of shirt to make a pleasing “outfit”.

Free tip for the dudes: don’t have any idea what colours to put together? Just take off your pants. Seriously. Men’s clothes often has cheat sheets built-in. Look at the inside of your pants and you may find a patterned or different colour fabric. If the rest of your outfit contains the same colours as that fabric, you’re set.

Embarrassment bred obsession

Here’s where it gets a little fucked up. I learned a ton about fashion and clothing and fit and accessories and shoes and hats (don’t wear hats) and the more I learned the more I was mortified.

Looking back at my old outfits, it was as if I discovered I had spinach in my teeth for my entire life. And not like a tiny piece of green between the back molars, we’re talking an entire incisor obscured by a plant.

WHY DIDN’T ANYONE TELL ME I LOOKED LIKE THIS?

Mexico in 2010, a point at which I actually thought I had my shit together. Was also at the height of my Threadless obsession.
Mexico in 2010, a point at which I actually thought I had my shit together. Was also at the height of my Threadless period.

Anyway, once I realized this, I then became obsessed. Everything had to match now. Everything had to be perfect. Everything had to fit just right. The shoulder seam had to hit in the right place and the sleeve length needed to be perfect and the pant cuffs had to be rolled up exactly right and my socks had to have a pattern that was fun but not clashing.

Oh man, this shirt tail ends only an inch before the bottom of my back pants pocket, is that too long to wear untucked?

Are these shoes too casual for this event? Or am I doing that thing where you wear casual shoes and jeans but have a dressier shirt? Are these shoes good enough to do that with?

Does my ass look as good as my ass can look in these pants?

The short sleeve on this shirt isn’t exactly parallel to my arm. Dammit.

I spent so much time worrying about every little detail that it was making me bloody miserable. I would go on shopping trip after trip and end up with nothing because nothing was “perfect”.

When I did find something that was close, I spent a fortune on tailoring to get the sleeve length or body width just right and I would (seriously) ask them to re-do it if they got it wrong.

And then, when I would nail an outfit (in my mind) I would strut proudly out the door only to see pictures later on that revealed some other imperfection.

Can you have body image problems with clothes? Cause fuck me, I had that.

Also, I became a judgemental prick in my head

Once I knew the “rules” I couldn’t help but apply them to everyone around me. I’d see a man in a white dress shirt with a white undershirt and want to tell him, “excuse me, you should try a heather-grey or skin-tone undershirt so the lines aren’t so visible.”

I didn’t, though. Because I didn’t want to get punched. I don’t like getting punched.

With my newfound knowledge I wanted to “fix” people. I felt superior. I felt like “Ah ha! Now I’m a person worth existing!”

Was I not worth existing before because I only wore a pair of Reeboks? Is someone who doesn’t put effort into dressing lesser than those who do? Fuck no. That’s nonsense. Some of my favourite people don’t give a single god damn about those “rules”.

Perhaps the supreme irony here is that I’m more embarrassed by my obsessive behaviour and elitist attitude now than I ever was about not knowing how to dress. Not understanding something is a lot better than understanding it and using that knowledge in distructive ways.

And more interesting: I hate most of the clothes I bought during that period. It may look alright but it doesn’t make me happy. I don’t like to wear most of it.

My fashion belief now? You should love wearing your clothes above all else. And if you hope people notice what you’re wearing, that could be an issue. (Of course, it’s still the way you feel and that’s okay and you shouldn’t run from your feelings, but it might be worth taking a closer look at why you want people to notice your clothes.)

Relaxing in two senses

Last night I went through my entire closet and looked at every piece of clothing. If I loved wearing it, it stayed. If I didn’t, it went into a pile to be donated. 90% of that pile is clothes that looked amazing, “fit” perfectly according to the “rules” and yet I never wore because as it turns out looking good is bloody uncomfortable.

I would often wake up, decide between looking good and feeling comfortable and make up excuses why I should feel comfortable.

“I’ve got a lot of coding to do today, better put on my older, less-flattering, comfortable pants even if I don’t look as good.”

“I’ve got a long day of meetings. Older, less-flattering, comfortable pants.”

“I’ve got … to eat lunch later. OLFCP.”

So my ass doesn’t look as good and the comfy pants are older and more run down. But, really. Who gives a single shit? Tomorrow no one will remember what you wore today. As I think I’ve demonstrated here, we’re all far too concerned with ourselves to notice others.

A, uh, conclusion?

I love this blog because I don’t feel any need to be coherent. Posts don’t have to have a topic and a middle and an end. It’s my blog. I can ramble for a while and then stop and then hit publish. That’s the whole damn point.

This blog is my older, less-flattering, comfortable pants.

Which is a completely irrelevant point because my actual conclusion is this: dressing should be easy and fun and without pressure.

Now, don’t get me wrong, my clothes will still match (usually) and I won’t just wear any ol’ damn thing. My shoes will have round-toes and no complicated designs. But I want to feel okay to wear stuff off-the-rack even if it’s not perfect. I just got a hoodie that’s a little too wide and the sleeves are little too long but I love it. If my pant legs are a little too long – so be it. Who cares if I’m too short for pant stacks. Or maybe I’ll just roll ’em on up. Whatever gets the job done.

This doesn’t have to look bad by any means. For example, here’s my first dressed-up outfit free from obsession. The shirt and pants are off-the-rack, unaltered, and everything is damn comfortable. In my mind when I look at this photo I think that it’s not perfect but, shit, it’s good enough and doesn’t need the >$100 of tailoring I would normally have subjected it to just to end up with something _less_ comfortable.

From the opening party for our new office / cafe.
From the opening party for our new office / cafe.

As for my everyday? Well, I just ordered a new pair of Reebok’s for the gym but don’t be surprised if I wear them every damn day ‘cause these are so pretty.

IMG_1623

So, so pretty. I love you, neon green.

And yes, I ordered the green Apple Watch band to match the shoes. So I’m certainly not cured of my obsession.

But it’s okay.


The banner image of this post is of my actual wardrobe, in case you doubted my obsessive behavior at all. All the hangers match (and are wooden of course), the shirts are all organized by type and the whole thing is lit up like a shrine. The lights come on automatically when you slide open the wardrobe door. I designed and installed the whole thing with the thought that if I honor my clothing storage then I will be inspired to dress better. The reality: it’s kinda nice, I guess.