Mastery and Menswear


Since freshman year of high school, I’ve always dressed rather classically. In practice, that means I have far more suits than the average college student or Silicon Valley resident ever would consider.

I remember a menswear blog (dieworkwear.com), had this to say about the stages of learning how to dress well:

Michael Anton proposed on StyleForum that there were three stages to a man’s sartorial development.

The first stage was when he becomes aware of the basic rules and slavishly adheres to them. He also goes out and gets his blue and white shirts, brown shoes, and navy jackets, as he’s been instructed to.

The second stage begins when he tries to master more complex executions. He tries to pair more interesting patterns together; accessorize with pocket squares, boutonnieres, and bracelets; and maybe dandifies himself with colorful socks. The rules aren’t broken per se, but they’re stretched a little bit past the orthodoxy.

The third and final stage is when he tires himself out and goes back to the basics. He’s much more at ease with his clothes and isn’t such a stickler about rules. At the same time, he understands that fit is more important than fanciful executions, so he goes back to his basic color palettes and wears well fitting things.

You may see dandyish flashes at times when he wears checkered jacket here or there, but there’s nothing complicated about what he wears. This isn’t to say it’s a reversion to stage one, but rather an end point with subtleties that makes the basic look much more perfected and natural looking.

Reading that reminded me of something else I’ve read, the 5 stages of Mastery, proposed by Stuart and Hubert Dreyfus in 1980. (The following is ripped off Wikipedia.)

  1. Novice
    • “rigid adherence to taught rules or plans”
    • no exercise of “discretionary judgment”
  2. Advanced beginner
    • limited “situational perception”
  3. Competent
    • some perception of actions in relation to goals
    • deliberate planning
  4. Proficient
    • holistic view of situation
    • prioritizes importance of aspects
    • “perceives deviations from the normal pattern”
    • employs maxims for guidance, with meanings that adapt to the situation at hand
  5. Expert
    • transcends reliance on rules, guidelines, and maxims
    • “intuitive grasp of situations based on deep, tacit understanding”

The basic theme seems to be replacing the need for conscious thoughts with habit and intuition. However, a master in a topic can also consciously reason about a problem.

For example, I usually pick my socks at random. Most of the time, this works out pretty well.

But sometimes my outfit is unique enough that I have to pause and think about it. But I never have to think for too long since I can explicitly say what works, what doesn’t, and why.

It wasn’t so long ago when I was still stuck in Michael Anton’s stage 2. I still had no real idea of what constituted appropriate dress and my outfits tended towards the overly formal.

I’m sure all my coworkers had a great laugh last summer when I showed up to work in a necktie. In Silicon Valley.

After a while, consciously dressing up seemed little more than vanity. After that point is when I’d say my style matured.

I still have bespoke dress shirts and pants, and I’m a stickler for a good fit. But now, my relationship with the “rules” of dressing well is comfortable. I recognize them as guidelines that are somewhat arbitrary at times, but in general have an underlying reason for their existence.

Knowing that, I also know when breaking them is OK.

Pulling a Bill Cosby and showing up to a funeral in sweatpants is not one of those times.

That being said, I do have too many neckties. Time to finally start selling on eBay.

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