Learning About Fashion

An old friend of mine is visiting Vegas this week, and he’s been teaching me about fashion. Yesterday we went shopping together at the Forum Shops in Caesar’s Palace. I tried on different clothes while he explained some of the basic principles of fashion to me. We plan to go out again this evening. It’s been a very eye-opening experience for me.

For many years I shunned fashion completely. I’ve long considered fashion to be a complete waste of time, a pointless distraction for those whose temporal and financial abundance greatly exceeds their intellectual abundance.

This attitude is fairly common in the computer gaming industry where I worked for many years. Even if I was doing a presentation at a tech conference, “modern schlub” was perfectly acceptable. Nobody seemed to care how anyone dressed. Perhaps the only guy in that field I thought had any particular fashion sense was Dave Perry of Shiny Entertainment, but he was a rarity.

When I got into professional speaking, I learned to expand my wardrobe beyond ripped jeans and T-shirts. I added some conservative suits to my closet, but I didn’t wear them often.

My attitude towards clothing was based on comfort, functionality, and suitability for a particular occasion. As long as I didn’t have to deal with annoying social resistance to what I was wearing, I really didn’t care about what I wore. Since I worked for myself, I certainly didn’t feel I needed to impress anyone.

Another factor that made me shun fashion was my colorblindness. I don’t perceive colors the way most people do, so there are certain aspects of fashion that are difficult for me to comprehend. Even people’s skin looks different to me than it does to others. I’ve sometimes wondered what it would be like to be non-colorblind for a day. It would probably freak me out that human beings were suddenly different colors than I was used to.

When it comes to buying my own clothes, I often feel like I can’t trust my own eyes, so I typically play it safe. Most of my wardrobe consists of black, shades of gray, and some earth tones. When I’ve tried to take risks with color, I’ve usually failed, at least based on the feedback received from others. This seemed like a problem I couldn’t solve on my own, and I had little motivation to deal with it, so I basically stopped trying and retreated into my colorless comfort zone.

Reconsidering Fashion

A number of factors recently came together to shift my attitude towards fashion and convince me to take a deeper look at it.

First, a number of friends and readers have been encouraging me to make some improvements in this area. This feedback ramped up last year when I began posting photos on my Facebook page. When you’re in the public eye, you get a lot of feedback on all aspects of your life, whether you want it or not.

Second, Erin and I separated in October, so I became a bachelor again, something I haven’t experienced since 1994. This change has encouraged me to give other aspects of my life a makeover, as a way of letting go of the past and opening the door to a new future.

Third, after the separation I started getting a lot more attention from women (just as Erin did from men). I began going out more. A few of my friends, male and female alike, have noticed the recent expansion in my social life, and they’ve been encouraging me to pay a bit more attention to my appearance. I imagine they’re simply trying to be helpful.

Fourth, some of my more fashionable friends have been gradually educating me about fashion in small doses, giving me little tips here and there. I’ve been slowly coming around to acknowledge there’s actually more substance to this than meets the eye and that fashion can be used as a means of creative self-expression, much like blogging or speaking or making raw food concoctions. I also realized that it’s a lot more complicated than I first imagined and that it’s not necessarily something I can master in a weekend. I started opening myself up to the possibility that this might actually be a worthwhile endeavor… instead of writing it off as stupid.

Fifth, as I made certain changes to my wardrobe, I started noticing that people would treat me differently based on what I was wearing. For example, if I went grocery shopping while dressed very nicely, the checker would almost always be a lot more flirtatious with me, and female customers would sometimes open conversations with me. This virtually never happened when I dressed like a game programmer.

I can probably drop the word virtually from that last sentence.

And I know I can drop the word probably from the sentence before this one.

Sixth, I lost about 10 pounds since the last workshop, and many of my clothes no longer fit. I need new clothes that fit me.

Seventh, I’ve been going through a purging cycle lately. I packed up two thirds of my clothes to donate, the remaining third being mostly the essentials like underwear, socks, and gym clothes. So my closet is looking a bit barren now.

Eighth, I’ve had some direct offers from people willing to help me one-on-one, take me shopping, and give me an education in this area for free. It’s hard to say no to that.

So with this convergence of factors, if I’m ever going to learn about fashion, the time is now.

Learning by Doing

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.

Creative Self-Expression

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.”


“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.


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.

What’s Next?

I still have a lot to learn of course, but I wanted to share these beginner lessons as I learned them since I think they may provide some value for others too. I’m sure I have some readers that are even more fashion challenged than I’ve been. 🙂

One thing I don’t yet understand is how to combine different articles of clothing to create an overall effect that matches my self-expression. What goes with what? This part still has me confused, and it makes me nervous because of my colorblindness. How do I know what colors and styles and textures work well together? What else have I not even touched on that I still need to learn? At this point I’m sure there’s a great deal that I don’t even know I don’t know.

I’m guessing that perhaps each item of clothing I wear can play a role in collectively contributing to an overall message, like individual actors in a play. It may be rather difficult, for example, to find a shirt that communicates everything I’d like to convey, but I may be able to put together a complete outfit that covers 80% of what I wish to communicate, and perhaps that’s good enough. At different times I may also wish to emphasize different aspects of my personality while downplaying others.

I’m like a newbie martial arts student who learned one punching and one kicking technique and thinks he’s ready to spar… totally oblivious to the fact that he has no clue how to block or dodge yet. If I try to go shopping on my own now, I’ll probably get beat up, but I’m gradually learning.

If you happen to be a fashion expert and would like to assist with my fashion education in Las Vegas (preferably in person by going shopping together), let me know. Whenever I get into something new, I like to use the strategy of immersion and move through the beginner stage as quickly as possible until I feel like I’ve achieved some level of basic competency. I usually find the beginner stage of a new endeavor to be the most fun because that’s where we learn the fastest. We just have to give ourselves permission to completely suck at something new and to be okay with our own incompetence.

Some people have requested that I post some pictures of my new outfits. I may do that later, but I haven’t bought anything yet. For now I’m still learning the fundamentals, so hopefully I’ll be confident and competent enough to shop on my own someday. Asking for pics at this point is like asking a newbie martial arts student to show you some video of his kicks and punches. It’s not going to be all that exciting just yet.