Next we started going to some stores. He asked me to look at the mannequins and take note of any clothes that seemed interesting to me and that I thought might be a good fit for me.

That part was difficult for me. In the first store we entered, I immediately saw an outfit that seemed interesting at first glance, but my doubts kicked in, and I mentally ruled it out just as quickly. It wasn’t like anything I’d ever bought or even tried on before. So we circled the whole store, nothing really grabbing me, and then when we came back to that same outfit, he noticed me staring at it and asked me what I thought of it.

As I touched the gray slacks on the mannequin, I said, “I kinda like these pants.”

“Why?”

“Well… they have some texture and a subtle pattern. They aren’t a plain solid color. There’s richness and complexity here, but it isn’t glaring. These pants aren’t dull and boring, but nor are they trying too hard to stand out. They also seem to be of high quality. I’m not exactly sure why I like them though. They just naturally draw my attention.”

“Do you realize you’re describing yourself?”

Errrrrr??? Mental rewind and replay of what I just said… Hmmmm… He’s right. That’s weird… What does that mean?

I found this to be a really cool insight. As we continued shopping, I started describing each piece of clothing I saw that looked interesting. Then I asked myself whether or not that description fit me.

This process reminded me of dream interpretation. When you describe one of your dreams, you can interpret it as a description of some part of your life. For example, if you say that you had a dream that you were starving and that no one was giving your food when you asked for it, it could mean that you’re experiencing scarcity in some part of your life and that your current social circle is reinforcing that scarcity.

Over the course of an hour or so, I began to notice some commonalities in the clothes I liked vs. those I didn’t like.

I don’t like plain solid colors. Those seem very boring and drab to me. The funny thing is that most of the clothes in my closet right now are plain solids. Perhaps that explains why I feel bored and uninspired by clothing in general. My current wardrobe constantly reinforces that feeling.

I also don’t like loud, obnoxious looking clothes. I feel they’re trying too hard to stand out and be noticed, like they’re needy and desperate for attention.

I don’t like shirts with high contrast light and dark vertical stripes. They look too corporate, too rigid, and too uncreative. They also look like bars and remind me of jail.

I don’t like ties. They scream “corporate slave collar” to me, even if they’re really colorful.

I love items that have some subtle complexities to them without a huge degree of internal contrast.

I liked a white shirt with thin off-white stripes. At first glance it seems like a regular white shirt, but then you’re drawn to look again and reconsider your first impression.

I liked a rich blue shirt with thin zig-zag stripes in medium-contrast shades of dark blue. When I first looked at the shirt, my initial impression was that it was too busy, but it made me want to keep looking at it, and I realized that there was a geometry to it that made sense. I probably would have bought that shirt if they had it in my size, but unfortunately it was too big on me.

I liked items that looked like solid colors from a distance, but as you get closer to them, a greater level of complexity and richness emerges, almost like zooming in on a fractal. Look at a leaf from a distance, and it may appear to be solid green, but up close you realize that it’s anything but simple.

I began to see that my preferences in clothes reflected different aspects of my life. For example, many people like to classify me with broad strokes (i.e. label me a solid color) after reading a few articles of mine. However, those who know me best are able to see the complex subtleties of my personality.
Details

My friend also helped me notice the subtle details of different articles of clothing.

Why did the designer put an extra pocket here?

Why is this line slanted instead of straight?

Why two kinds of fabric instead of one?

I’m not used to noticing this sort of thing. My work has more to do with synthesis and big-picture thinking vs. analyzing low-level details. Before yesterday I’d look at outfits as a complete whole. Now I see them in a whole different way. I assume that each detail is deliberate and purposeful and that it’s there to make some sort of statement. That statement may or may not align with my own creative self-expression.

To dress more authentically, my goal is to align the statements being made by what I wear with the messages I wish to communicate to others.

I noticed that I liked certain types of details but not others. I like subtle, complex details but not overly obvious or simplistic ones. I like items that whisper suggestively to me as opposed to those that scream for my attention.

If a piece of clothing is confident in its value, screaming is unnecessary. Perhaps that explains why I’ve never spent a dime to market or promote my work in this field. I simply rest in the knowing that it’s valuable enough to be worthy of sharing.

I didn’t buy anything yesterday — partly because finding the right sizes proved challenging and partly because we didn’t have a lot of time — but that wasn’t the point. The point was education. Now I feel like I can at least begin to identify articles of clothing that feel right for me. And the most fascinating bit is that these are the types of clothes I’ve never bought before, so if I step into this space with my wallet, I’m going to end up dressing very differently than I used to.