For a short time I tried to learn about fashion by reading about it. Some people referred me to online articles and other resources to help me get started. But honestly I couldn’t make sense of it. It seemed way too complicated, and the language was totally alien to me. I saw lots of clothing that didn’t appeal to me. It was like trying to learn martial arts by reading about it. You won’t get very good at sparring if your only opponent is a martial arts book.

I realized that I couldn’t learn this on my own. I needed someone to teach me interactively… literally go shopping with me, help me pick stuff out, and give me honest feedback.

So yesterday I kicked off that process. We only went out for two hours, but in that short time I probably learned more about fashion than I have in the past few years. I can’t imagine trying to learn this any other way.
What I’ve Learned So Far

I’m a total newbie at this, so these lessons may seem a bit beginnerish to you, but they were profound and eye-opening for me.

First, my friend explained to me that how we dress on the outside can reflect who we are on the inside. That’s when we’re dressing congruently. I understood the basic idea, but I rarely felt that I was dressing congruently.

He asked me to share some adjectives for what I wanted to express. What do I wish to communicate to others about the kind of person I am on the inside?

That part was easy for me. I rattled off a list for him in short order.

I want to express that I’m intelligent and authoritative, but in a way that’s flowing and creative, not in a stuffy or inflexible manner.

I want to express that I’m open, friendly, and approachable, not cold or aloof. I want people to feel they can easily start a conversation with me and get a positive reception.

I want to express that I’m strong, courageous, and free. I’m not afraid to take risks. I can easily function within society, but without being oppressed by social conditioning or succumbing to pointless rebellion.

I want to express that I’m passionate and happy. I enjoy life fully.

My friend has known me for about 25 years now — we went to high school together — so he was able to draw on his knowledge of my character and personality to help me round out this image. He explained that I’m something of a paradox. He noted that it was odd, for example, that I’m very intelligent and successful in business, but socially I’m such an easy-going, approachable, and down-to-earth guy to talk to. Also, I tend to be very creative and borderline eccentric in the stuff that interests me, yet I have no trouble functioning perfectly well in normal society (if you can call living in Las Vegas normal).

He explained how all of us have paradoxes within us and that what we wear can express that. He shared some of his inner paradoxes and showed how his clothes reflect it… and that he’s able to get away with it because it reflects his inner self accurately.

We hadn’t even gone into any stores yet, and I was already fascinated at this point.