Confessions of an Ex-Preppy

On Sunday, June 15, I went with Catherine to a reception after Mass at her church for a newly ordained priest. I found myself doing something I’ve never done before but which I’ve often seen Catherine do: I set my clothes out on the bed before getting dressed. I wanted to be sure they weren’t too wrinkled, that they went well together, and that I felt like wearing them as opposed to something else.

Doing that was extremely unusual for me. Before my shopping trip a couple of weeks ago, I wore one kind of pants every day: flat-front khakis from J. Crew. I had three pairs of the same style. I had a couple other pairs of pants, but I wore something other than khakis about three times a month. On the evening of May 26, I was walking with Catherine through the SoMa neighborhood to a party after work. I was looking at how all the men we passed were dressed, so fashion was on my mind. While standing on the corner of Second and Bryant waiting for the light to change, I thought about how I wore the same style of khakis every day and joked to myself that it was some kind of psychological disorder.

Later that evening, I thought that the joke was half-serious. Not being into fashion is one thing, but it seems pretty extreme to be content to wear the exact same style and color of pants every single day of your life. Most people wear uniforms only because they’re forced to. I had strong resistance to the idea that I should pay much attention to fashion. Now here I am setting my clothes out before I wear them. It makes total sense, but it is nevertheless a weird experience to find myself doing something like that.

In addition to spending more money on clothing, now I’m spending more time thinking about it every day. Mornings are more stressful now, because instead of just wearing the same pair of khakis until they need to be washed and swapping them out for an identical clean pair, now I have to think about what to wear. Every day it forces me to ask myself, “Why am I spending more time and money thinking about how I dress? What do I want out of this? Is it worth my time? How can I get more Ted Baker shirts at less than full price?”

One thing my mind does well — too well, probably — is create categories out of a mass of undifferentiated information. I’m almost like that kid in The X-Files who finds detailed patterns of information in the static on a television screen. So I’ve been creating categories of people based on their motivations for paying attention to fashion, and trying to figure out where I fit in.

To Focus Others on Your Surface and Avoid the Gnawing Emptiness Within

The motivations that AskFratBoys.com appeals to are some of the basest motivations men have. Frat boys are probably the most insecure group of people on the planet. Inside they are like scared kittens; that is why they lift weights, swagger, display gratuitous bravado, and become such caricatures of masculinity. Um, now, not that I know anything about frat boys first hand, mind you, not like I ever was one myself.¹

When airheads — male or female — get interested in fashion, it’s pretty much just the narcissism of minor differences. That’s one of my favorite concepts from Freud, that people in adjoining countries or cultural groups focus on the minor differences that distinguish them instead of the vast number of important factors they share in common. For example, Americans and Mexicans, Germans and Britons, Indians and Pakistanis, the Hatfields and the McCoys, Republicans and Democrats — all those pairs of groups have far more in common than not, but they’ve all had terrible conflicts with each other. It’s a form of narcissism that enables weak people to find refuge in a group identity. This is the opposite of where I’m headed, towards a focus on one’s individual character. I suspect that I am going to have enormous amounts of fun using my superior intellect and devastating wit to mock the unsuspectiing frat-boy segment of the men’s fashion world. It will be my version of Revenge of the Nerds.

To Save Western Civilization From Itself

Another motivation for paying attention to fashion is to express one’s cultural superiority. This kind of person thinks that the subject of fashion is beneath them and that only shallow people could possibly be interested in it. People like this subscribe to policy magazines, own copies of the Encyclopaedia Britannica, and want to write blogs on politics. Um, again, it’s not like I was ever part of this group, either, you understand.²

This is also the narcissism of minor differences. We’re all Americans, Westerners, humans. I think my identity as an intellectual kept me apart from mainstream culture for a while, looking down at it. I will never stop hating anti-intellectualism, and it seems like much of the culture of fashion is anti-intellectual, but I’ve begun to see that much of it isn’t and that there are plenty of deep reasons to be interested in fashion. So I don’t want to be a part of this group, either.

To Write Your Dissertation

I’ve known some people who aren’t very concerned with fashion but who know very little about it and who don’t hate it. They are merely uninterested. They have truly never given it a second thought. A lot of intellectuals are in this category. They dress horribly, but they’re wonderful people, and very intelligent. They’ve just never had any reason to think about how they dress because they’ve never known an intelligent person interested in fashion. Everybody they know is extremely smart and practices the hyper-specialization encouraged by the culture of academia. Not only do these people know nothing about fashion, many of them also don’t know the name of the current president. But they could give an impromptu one-hour lecture on the tension between classicism and romanticism in 18th-century German literature. I’ve never been a member of this group.³

I also know someone who said she used to be heavily into fashion but just reached a stage in her life when she got less interested. I don’t know her reasons, but she didn’t express a judgmental attitude toward fashion, so I put her in this category.

I don’t see any major problem with these kind of people, except that they’re tolerating mediocrity. I don’t want to be in this group.

To Avoid Mistakes

I know a lawyer who mostly works from home and dresses like a teenager. But once I saw him iin a suit, and he obviously knows a little more about what’s current in suits and ties than I do. He’s not really into fashion, but he has learned enough to avoid making mistakes that could hurt him professionally. Clearly I’ve been bitten by a bug that has gotten me more interested than that.

To Keep One’s Outer and Inner Selves in Harmony

I love the quote from Armani that “clothing is the outward expression of the inner person.” Again, I don’t know exactly what he had in mind, but I think that development of one’s inner person is one of the highest goals one can have. There are so many conceptualizations of it. A modern one that most Westerners can relate to is Maslow’s concept of self-actualization. I think the one I like best is Jung’s concept of individuation.

It is the polar opposite of the frat-boy approach, which is to subsume one’s individuality in a group. In fashion, this is the stupidity of buying something just because “it’s the trend for 2008.” I remember a hilarious segment on MTV, I think from when I was in college. It was when Madonna had just become a superstar, and she had this distinct way of dressing. About five girls were in the mall, and they all dressed like Madonna. The only thing I remember from the interview was one girl saying, “We dress this way to express our individuality.” She was standing right next to four other girls dressed exactly like her.

By contrast, I remember a conversation with Catherine in which she said that what you do is try different styles and then create your own look. I’ve since heard that from others, and seen the same attitude in various places in the fashion world. That rings true. That’s what I want to do. I am seeing this first phase as one of experimentation. I want to move beyond the 1980s Southern Preppy style where I subsumed my identity, but I don’t know yet what my own personal style will be. If it’s like other areas of life, my guess is that it will be about a year before I get it right. I’ll probably laugh at some of the things I bought on my shopping spree last month, not because there’s anything ugly about them but because they just don’t suit my style.

I hope that everything I do somehow honors that which I consider the highest: truth and beauty.

I hope that my outward appearance can be as truthful as possible, that is, that it represents my inner character as much as possible. To dress as conventionally as I have dressed all these years is almost deceptive, because I am so unconventional.

I also hope that if I have a choice between something that is more beautiful and something that is less beautiful, I will choose the more beautiful one every time. When I walk down Market Street in San Francisco and I come across someone who is dressed well, I almost want to shake his hand and say, “Thank you for making the world just a little more beautiful.” Imagine a city where everything was as beautiful as it could be. Imagine cities where subway stations were designed by architects like Frank Lloyd Wright instead of engineering firms that also build prisons. Imagine offices where even the departmental phone lists done in spreadsheet software were designed by professional graphic designers. Imagine a crowded sidewalk where nobody was dressed any differently than they are now except that everything fit properly. The world would be so much more beautiful. I think that increasing the amount of beauty in the world is so important that I should learn at least a little bit about art, literature, music, fashion, architecture, and design so as to better appreciate beauty in all its forms and to choose more of it in any of these areas. I’ve been reading encyclopedia articles on the philosophy of art because philosophers have been thinking about the nature of beauty for thousands of years, and I want to use their insights to help me think about my involvement in fashion.

1. He’s lying! He was a preppy Sigma Pi at a Southern university. [↩]
2. He’s still lying! He was exactly this kind of person until Catherine proved that one could pay attention to fashion without damaging one’s I.Q. [↩]
3. He’s telling the truth this time. He’s never dressed like some of his acquaintances in academia. [↩]

As I read more, I am becoming more aware how different my motivations are than those of many other men who get interested in fashion.

In the Details Men’s Style Manual, the first spread has eight style rules. Based on my conversations over the past few months with Catherine and with other intelligent people who are interested in fashion, this set of rules strikes me as intelligently chosen. Furthermore, several of the rules point to the role of one’s character as the most important influence on one’s choice of clothing.

The same book also has a handful of spreads with eight to ten small paragraphs from famous designers. One designer is Giorgio Armani, and his spread begins, “Clothing is the outward expression of the inner person.” It was another encouraging indication that I may encounter kindred spirits in the fashion world. Of course, it depends on what exactly he means by “inner person.” I don’t know anything about him. Maybe he thinks it’s just a nice-sounding thing to say, or he could have spent 20 years in Buddhist monasteries for all I know. At any rate, I doubt he’s into the kind of Olympics-level navelgazing I do.¹ Still, Armani’s quote is nice to see, because so many people who are into fashion seem so shallow. For example, other people’s spreads in the Details book give every indication that they have little inner life. They almost all seem like nice people, but I probably wouldn’t be able to relate to them because they seem preoccupied with the surfaces of things.

Take the Introduction to another one of the books I bought, The Style Bible. It’s totally schizophrenic, or maybe I’m just misreading it. It starts out pretty good: “As boys, we are taught that masculinity and a concern for style are incompatible. Fashion is the domain of the woman, and too early an immersion in it might put us on the path to becoming sissies.” There’s a lot of stuff there that triggers my Jungian reflexes. I set in boldface key words that point to the power of formative experiences. I think this writing is profound. For me at least, experiences in adolescence certainly contributed to my hostility towards fashion. I was raised in a very damaging form of Christian fundamentalism where anything involving the human body was seen as sinful. For me, a healthy attitude towards fashion demands examination of my childhood and youth. It feels a little like therapy.

The next paragraph also has a powerful nugget: “What we are advocating is the simple act of setting oneself as the primary criterion in dictating what one wears.” The phrase I set in bold triggered memory of teachings in various religious, philosophical, and mystical traditions I’ve been involved in. You find the same thing in ancient Greek philosophy, yoga, the Bible, Buddhism, and shamanism: a moral injunction to know thyself. If you don’t know yourself, you can’t be confident of your judgments about anything. A lot of people seem to grasp that intuitively, but in my youth, life was all about unthinking obedience to somebody else’s rules. My intuition and emotions were not to be trusted, because that’s where Satan could lead me astray. Many ancient traditions set one’s self as the primary criterion for making moral judgments. Everything has moral implications, and I want to consider the moral implications of my fashion decisions.

The Introduction goes on to make really stupid jokes, like the kind of lame attempts at humor that copywriters in ad agencies create for big, stodgy, bureaucratic corporations that try to brand themselves as though they were rappers. The I.Q. of this book has just plummeted. Then a few paragraphs later there was something that made me mad: “We know that you are not interested in boring historical backgrounds, so we will stick to the practical, functional advice….” I’m a nerd. I started wearing glasses in the fourth grade. I used to have a problem with compulsive book buying. I own a copy of the Encyclopaedia Britannica. In the last few days I printed out long encyclopedia articles on aesthetics, the philosophy of art, and the history of Western fashion. The writer isn’t saying that he’s only against those historical backgrounds that are boring; clearly he thinks that all historical backgrounds are boring. He has just declared himself to be my enemy.

So now I’m curious to know more about who’s produced this book. The cover has before the title, “AskMen.com presents.” So I go to AskMen.com. Wow, that explains it. That is one of the dumbest web sites I have ever seen. It is for frat boys. It should be AskFratBoys.com. I appreciated that the Details book contained the phrase “inner life,” so for fun I decide to search AskMen.com for that phrase. (Actually, the phrase in the book was “inner person,” but I didn’t realize that at the time.) For some strange reason, the search engine changed the query to “emily proctor,” the name of an actress. I didn’t see at first that the query had changed. I clicked the first result. It seemed to be part of a section devoted to celebrities. I searched the page for “inner,” and it yielded no results. I scrolled down. In her biography, it lists various films she’s acted in, and about one film, the only detail the site editors felt was important to mention was that it “called for her to appear topless.”

I guess if I want Jungian insights into men’s fashion, I probably shouldn’t ask the frat boys at AskMen.com.

1. If everybody in the world were like me, then navelgazing would be an Olympics sport, though I have to admit it wouldn’t make great TV unless the Olympics went back to the way they were in ancient times, where everybody was naked. [↩]

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.