Confessions of an Ex-Preppy

About nine months ago, I was so unconcerned with men’s fashion that I didn’t even know that pleats went out of style some time after I was in high school in the 1980s. Yesterday, in Union Square in San Francisco, I bought more clothes in four and a half hours than I normally buy in two years or longer. That concentrated burst of shopping was a sudden result of a slow expansion of my consciousness that has been developing for about a year. Major changes in complex systems such as climates, economies, and psyches often appear to come out of nowhere but are actually tipping points that are based on many small, incremental, barely noticeable changes. Far from being an impulsive act in a mid-life transition designed to make me feel younger, yesterday’s shopping trip was a carefully planned event based on a significant amount of primary research, secondary research, and analysis.

It has been a fascinating process, and at times it has been both uncomfortable and exciting, and sometimes both at the same time. I have the feeling that it has only just begun in earnest and will continue the rest of my life. It has been a process of self-development, fulfillment, self-acceptance, relaxation, love, and even worship. The process of becoming more aware of men’s fashion has made me think deeply about my character, my deepest values, my relationship to others, my relationship to my society, politics, history, culture, and collective psychology. This blog will be about what has caused such a transformation in my consciousness, and it will be a record of how that consciousness develops, and hopefully it will serve as a guide to other men — and women — who want to make the world a better place by making it more honest and beautiful.

About Me

I am a 43-year-old consultant living in Berkeley, California. I help companies document and improve internal publishing operations. I grew up as a preppy in the South. My father was a banker, I went to private schools, and I practically lived at a country club all summer. Many of the parents of my childhood friends were from prominent old-money families in politics and business.

Despite my upbringing, I’ve never cared terribly much about my career or about making a lot of money. My main motivation has been to know God, and when I lost the ability to believe in any god, my main motivations became threefold. One motivation is to expand my consciousness as much as possible. Over the years I have tried many drugs, meditated many hours, and lived in three ashrams. I settled on a handful of techniques that worked for me as a way to develop a state of heightened awareness, and I try to practice at least one those techniques at any given moment. A second motivation is to be as intellectually and emotionally honest with myself and others as possible. The pre-Socratic tradition of arete, what we might call excellence of character, and the practice of Jungian psychology have been very effective for me. A third motivation is to honor beauty by seeking out experiences and environments that make me feel beauty, and by making things around me beautiful. I cannot get very involved in anything unless it triggers all of these motivations, and men’s fashion has done so.

What Changed My Approach to Men’s Fashion

I have always wanted to see myself as someone who was above wanting to make some kind of statement through fashion. I wanted to be sure I dressed better than most people, which these days is hardly difficult, but I just didn’t care to spend any time learning the finer points of style.

What started to change my approach to men’s fashion was the thing that is probably responsible for many a man’s fashion awakening: I met a woman. My girlfriend Catherine has a very highly developed sense of visual aesthetics. She has a degree in graphic design and worked as a designer for years. She’s always loved fashion, and she started her own clothing boutique on Polk Street in San Francisco and ran that for years, and then she was the manager of a J. Crew store. Now she’s back in the design field and also beginning work as a model.

The first tiny incremental change that led to yesterday’s shopping expedition was nearly a year ago, when Catherine convinced me to buy a pair of flat-front khakis. She pointed out that pleats were no longer fashionable. I seriously had no idea. My father told me in high school that pleats were fancier, and that was the last input I’d had on that subject. Yet even that tiny incremental change was based on tiny incremental interactions with Catherine. I have always thought that people who were into fashion were shallow. Advertising, television shows, movies, and rock stars certainly do little to correct that impression. But after years of knowing Catherine and months of dating her, I had irrefutable proof that I had been wrong. I was incredibly attracted to Catherine, and I can’t be attracted to anyone, male or female, for very long unless they can challenge me intellectually and are open to me challenging them intellectually. Catherine was more into fashion than most people, and she was also one of the most thoughtful, reflective, and intelligent people I’ve ever met. Over time I think I began to understand that her interest in fashion wasn’t just in spite of her depth, it was directly related to it. I could trace it all the way from her depths up to her surface. So when she called my attention to the fact that I was way behind the fashion, it didn’t provoke my usual responses to people who only seem to be interested in the surfaces of things. And of course, it was a pretty small step. If I didn’t like plain-front khakis, I could always go back to pleats with my next purchase.

Three Phases of Evolution of My Men’s-Fashion Consciousness

Looking back over the last few months, I see three phases in the development of my men’s-fashion consciousness. The first phase was passive reaction to Catherine’s suggestions. The second phase was active involvement with and genuine curiosity about men’s fashion. The third phase began with a sudden insight that marked the beginning of my own relationship to men’s fashion.

Phase One: Passive Reaction

I take my experimentation with plain-front khakis to be the beginning of the first phase. This phase was marked by consideration of men’s fashion, but in a relatively passive way, that is, just in reaction to Catherine’s direction of my attention. I was developing a vague sense of trends. Not long after getting me to move beyond pleats, Catherine convinced me to change my conservative preppy haircut to a Caesar haircut. Despite my attraction to Catherine and appreciation for her intellect, I am still not sure what made me open to this idea. Sure, you can let a haircut grow out and go back, but that’s different than buying a pair of pants without pleats because a haircut lasts at least a month. I was much less comfortable with the new look, but it got such positive reception from so many women and it turned Catherine on so much that I decided to stick with it.

But during this first phase I was still relatively hostile to the whole subject. Not long after getting me to change my haircut, Catherine pointed out a pair of shorts from Hickey Freeman online. As I always did when considering an article of clothing, the first thing I looked for was the price. The shorts were $150. I felt a visceral sense of disgust and almost a sense of betrayal toward Catherine that she would think I would even consider spending such a sum on one pair of shorts. How could she misunderstand me so badly, to think that I was one of those people? One of our first significant personal arguments was about fashion. Even though she told me you look at expensive clothes just to get ideas, I just didn’t get it. That whole experience set me back months.

Eventually, though, continued exposure to an extremely thoughtful fashionista and many intellectually challenging conversations about fashion opened my mind back up to the subject. In particular, my conversations with Catherine began to explore fashion through the lens of Jungian psychology, and I came to understand how our fashion choices are expressions of desire that have been influenced by formative childhood experiences. Also, in venues about fashion such as Go Fug Yourself I saw lots of interesting material at the intersection of the personal and collective psyches.

Phase Two: Active Involvement and Genuine Curiosity

My second phase began very suddenly just a few weeks ago, on the evening of Tuesday, May 6. In this second phase, I moved from passive consideration to curiosity and active involvement. Catherine was going to acting class after work, so I was in no rush to get home. I was in a state of heightened awareness, and I was captivated by the scene on Market Street in San Francisco. I had always walked to the subway quickly, thinking only about getting home, but this time I was absorbing everything. I was extremely relaxed. I looked briefly but very intently at everyone I passed, and it was so much fun that I decided to keep walking past the entrance to the subway.

Everything I was seeing was sparking a lot of interesting thoughts about politics, my usual intellectual obsession. I’m not sure why, but I suddenly got the idea to look for beautifully dressed people, so I headed towards Union Square, thinking I might see well-dressed people shopping for nice clothes. It was a fascinating experience to look at every single person and quickly size them up as fashion-aware and fashion-unaware.

One thing that struck me was that extremely well-dressed people seemed to number about 1 in 100. I was shocked at how many people dress poorly, in cheap clothing that doesn’t fit them well. Another interesting insight was that in general, the young black men who dressed like rappers had a better sense of fashion than middle-class women. That amazed me. Of course, the fashion of the young men was garish and ostentatious, but they at least had a more developed sense of color, material, and coordination. I didn’t like their style, but I could appreciate that they were more educated about fashion than most of the middle-class women in Union Square. And the guys — that was truly depressing. I passed hundreds of men, and I can remember only two or three who were really well-dressed. They had good quality clothing that fit their bodies well and went well together. One of them was obviously gay and was wearing a gay uniform. He was dressed in very nice preppy clothes, but all his clothing looked like it came from the same company or something; I didn’t feel like I really got a sense of who he was as an individual. The vast majority of men had fairly nice clothing but that fit them poorly.

I was excited and felt close to Catherine, because I’d never walked through the world before being aware of fashion. “This must be something like how she sees the world,” I thought.

The most inspired dresser, in my view, was a young Asian woman in a bookstore who looked like she was in college. None of her clothes were very expensive, in fact they all looked extremely affordable, but everything was good quality, fit her impeccably, and was very well coordinated. Fortunately she was looking down at a book, and as I was riding up the escalator I could afford to get a long look at her down on the first floor. Her hair and her eyeglasses perfectly complemented her face. She was wearing a loose but well-fitting black blouse, a short black-and-white skirt with a pattern of squares, black leggings, and black flats (I just now learned that term by doing a little Googling!) with silver buckles. She was truly inspiring, and I felt grateful to her for setting such a good example. She had to have had on one of the least expensive outfits out of the hundreds I saw, but she was one of the best-dressed people of the evening. It was a real eye-opener, because it showed me that you don’t have to spend a lot of money to look great. You just have to choose wisely. The world of fashion now felt much more welcoming to me.

In the days that followed, as I analyzed the experiences of that evening, I saw in a much more personal and visceral way the extent to which one’s approach to fashion was determined by one’s consciousness. Many experiences on drugs and after meditation showed me that expanding one’s consciousness is largely about reducing one’s resistance to things. When we resist something, such as the subject of fashion, we literally filter it out of our experience. I’d walked through Union Square before, but I’d never even begun to experience the differences between fashions and the aesthetic, intellectual, and moral reactions they provoked in me. It was much like the experience of walking through an art museum. In the days that followed, my experience of walking down Market Street was utterly different. There was an entire layer to that whole scene, right there in front of my eyes, that I was completely missing.

Six days later, on Monday, May 12, I took my active involvement further by buying three men’s fashion magazines. In the days after my trip through Union Square, Catherine and I had several interesting discussions about fashion, and she suggested that I buy some men’s fashion magazines as a way of getting ideas. I looked puzzled and said, “There are men’s fashion magazines? I mean, I know about GQ, but….” She started laughing and looked at me in disbelief. On Monday, she took me to a bookstore after lunch and showed me. I got the current issues of GQ, Men’s Vogue, and Details. Looking through them was interesting. There were certainly a lot of shallow material in both the ad and news columns, but I was still surprised at how much useful information was in there, for example, how to choose the right shape of sunglasses for your face (the standard preppy green aviator glasses I’d favored since high school were still fashionable but their shape wasn’t complementary to my oval face), how to avoid the worst shoe mistakes (I had been), and helpful photos showing people in outfits with the prices of all the items, again showing me that one can look extremely fashionable for barely more money than I’d always spent on clothes.

In addition, one magazine had an interesting article on how evangelical Christians have taken over entire Army bases and brigades in Iraq and think that the war will trigger Armageddon and bring Jesus back in a few years. I get overdoses of political news elsewhere, but it was nice to see some political awareness in back of the magazine to help balance out all the airheads in the front. In addition, that story had balls. The mainstream media doesn’t have the courage to stand up to the evangelical Christians in Washington, D.C., who are running the military and the country into the ground because they’re so out of touch with reality. This story had nothing to do with fashion, but I appreciated the editors’ inclusion of material that was not superficial.

Phase Three: I “Get It”

The third phase in my evolution of men’s-fashion consciousness came on Wednesday, May 21. I had looked through my three fashion magazines for a week, but looking back now I can see that I really didn’t make a distinction between what was going on in an Armani spread compared to a Dolce & Gabbana spread. I find that pretty funny now. Anyway, on May 21, I was in a state of heightened awareness and I decided to flip through one of my magazines again. This time, I had no resistance to the fashion advertisements. I was captivated by each one and entered into each scene. I saw huge differences between ads for Gucci, Prada, Jil Sander, Louis Vuitton, Dolce & Gabbana, and Armani. Each one provoked very different responses in me, though none of them were very favorable. At one point I realized that I had a very hard time relating to any of the models. They all looked so young, immature, and stupid. As kind of a game I started back at the beginning and asked myself with each model, “Can I imagine getting into a conversation with him about how ancient Greek philosophy and Jungian psychology relate to current events?” With every model it was, “No way.” The Dolce & Gabbana ad was a stylized version of an outdoor party that could not possibly be anywhere other than southern California and it had no one over 25. It made me wish there were a draft and all of these kids got sent over to Iraq and woke up to the fact that there’s a fucking world around them. Excuse me, but there really will always be some things about the fashion world that absolutely disgust me. These are the kinds of people on The Tonight Show With Jay Leno who can’t find Mexico on a map.

Then I came across an ad for Polo Explorer, a fragrance by Ralph Lauren. The model in that ad may not be a philosophy graduate student in real life, but at least I could imagine getting into an intellectual discussion with him. He was older, and he was the first really masculine man I’d come across. Every single other model so far had something extremely feminine about him. I don’t think there’s anything wrong with that in one individual person, but there’s something strange about how the immature, emasculated man is insanely over-represented in men’s fashion advertisements. Maybe as I learn more about the fashion world I’ll understand why that is.

Anyway, coming across the Ralph Lauren ad was extremely refreshing. Now here was a guy I might want to emulate. He had on a nice, dark blue T-shirt made of cotton. I had such a different visceral reaction to this ad. My whole body relaxed somewhat, and I felt more positive. Something in me resonated with this ad, unlike all the others. I had discovered what felt like a huge key to fashion: what works is what keeps me true to myself. This felt like a new phase, because no longer was I looking only where Catherine directed my attention. At this point I had my own relationship to fashion. I knew what to look for — that which resonates with me personally.

I subscribed to all three magazines, but I found myself wanting to take a step back and get a solid introduction to the world of men’s fashion. It would take a year’s worth of magazines to learn about everything, and I didn’t want to postpone my education that long. The next Saturday, May 24, I spent a few hours researching books on men’s fashion, and I ordered three.

Details Men’s Style Manual by Daniel Peres is a fantastic introduction. If you want to learn about men’s fashion and you can get only one book, it should be this one. It is quick to read and has lots of pictures. It begins with a handful of extremely perceptive rules of style that extended some of the insights I had had on my own over the past few weeks. It has a list of classic items everyone should own from overcoats down to shoes, which provided a perfect shopping list for me yesterday. Then it has a chapter for each major category: shirts, pants, shoes, and so on. Each chapter has an introduction to the various parts of an article of clothing, what makes a perfect one, different variations, details of style, how to wear one item in four different degrees of formality, one advanced tip, and a list of don’ts. It won’t tell you a lot of finer points, but it isn’t meant to. This book was made for me.

The next book I got was The Style Bible by James Bassil. It’s more of a traditional book, with much more text and no pictures, only drawings. It’s a good complement to the Details Men’s Style Manual because it covers the same territory but goes into more depth.

Finally, I got Men’s Style: The Thinking Man’s Guide to Dress by Russell Smith. It is a view of men’s fashion from a very individualistic perspective and one that is relatively intellectual compared to everything else I found. Smith feels like he’ll be a good guide for someone like me. I decided to buy his book the moment I came across this paragraph in an online sample chapter: “And if you think it’s amusing to break the rules of formal dressing by matching a dinner jacket with canvas tennis shoes, then you should stop reading immediately. You are angry about something, and want to be talking about politics instead.” His book covers all the major categories but from a strong perspective. I like how his first chapter is about the history and politics of fashion. It makes me feel like I’ll find kindred spirits in the fashion world. I’m not under the illusion that there will be many, but at least they are there.

By last week, I was irrevocably committed to buying at least one well-chosen item in each major category: shoes, pants, shirt, coat, and so on. I budgeted $1,000 for June. I was going to wait and gather a little more courage, but I wanted to take advantage of the last weekend of a sale at Banana Republic, where I knew I wanted to buy a lot of items. My books arrived last Thursday, and I had time only to read the Details book before yesterday’s shopping trip. I’m still digesting the others and will be writing about what I’m reading in the days ahead, and I’ll also be describing the individual items I bought, why I bought them, how much they cost, my insights from yesterday about how to shop, and how all of this is affecting my consciousness.

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