Confessions of an Ex-Preppy

There’s something I’ve been wondering ever since the beginning, when Catherine got me to start wearing plain-front pants: How should I have been able to determine that plain-front pants are better than pleated pants? How much of the choice between pleats and plain fronts is objective, and how much is subjective? Was there something obviously wrong with pleats I wasn’t seeing, or is it just a matter of personal preference? And that’s just one example among a possibly infinite number of fashion choices. In general, how do people evaluate one fashion over another — by what criteria?

Until recently, my only criterion for choosing one fashion over another was whether it was one I’d worn before. If I was familiar with a style, it was okay. Being a fashion bumpkin sure makes shopping easy! I’m used to getting everything from L.L. Bean, so why should I consider Banana Republic? Or when I’m in a Banana Republic store thinking about buying a shirt, what exactly should I be looking for in that shirt (other than the word SALE)?

Moses: “Before I give people the fashion commandments, God, tell me — does this robe make me look fat?”

Is there a fashion God like that of Judaism or Islam, or a group of gods like those of the ancient Greeks, from whence come unquestionable commandments and demands for bloody sacrifices of subservience? Will I be expected to renounce my old faith by throwing out all my L.L. Bean clothes? Is anybody going to expect me to bow at the altar of High Fashion with the priests of the runways mediating my relationship with Fashion God? Is GQ the Bible? If all this is the case, then some fashion pope somewhere is really going to hate me, because I’m going to make the mission of this blog busting his (or her — ha, ha!) balls. I’m going to lead tribes of pagan tree worshippers into the forest and put hexes on the priests of High Fashion. I have a problem with authority — not all authority, just authority for its own sake, incompetent authority, and authority whose main use of power is preserving its power.

Or is the fashion world full of sects based around charismatic, narcissistic leaders who encourage us to be happy and self-fulfilled? Is navigating the world of fashion going to be like encountering well-meaning but insensitive Christians, Buddhists, and ashramites whose leader makes them feel so good because they’re the perfect mother or father? Will devotees of different designers or styles earnestly try to proselytize me, politely pressurizing me to dress just like them because it’s good for my soul? If all that is the case, then I’m not going to want much direct engagement with the fashion world and will always feel like an outsider. I just won’t find many people who have a lot in common with my approach.

Click for larger image of an ad of tennis-inspired fashion.

Or is the fashion world more of a polytheistic, tribal world where different groups worship different deities with different values, none of them ever presuming to claim supreme authority over all the others? Is the fashion world kind of like the tennis world (another world, like politics, with which I’m extremely familiar), where some people like Federer, some like Nadal, some like this player, and some like that player, with no one even thinking of trying to argue that someone else’s choice is wrong? If all that is the case, then I’ll be much happier, because I’ll be free to grow naturally and organically into the style that’s healthiest for me, and I’ll be much more likely to find kindred spirits. I like the idea of discovering a San Francisco Bay Area style instead of something handed down from New York or Paris. I’d rather worship a god of the nearby river than a sky-god dictator of the universe or an arid scientific principle like a law of nature, which is just a sky-god in disguise.

So how do I set about learning how to make my choices in fashion? I feel a little bit like an anthropologist who moves to Alaska to work with Eskimos and needs to learn all their different words for snow. Whatever has been going on in the analysis of pleats vs. plain fronts has been too subtle for me. When making choices in any area of life, there are two things to think about: criteria and values.

Criteria: Deciding How to Make Choices

Snow on the ground is one thing, snow falling is another thing, snow in a pile is another thing, and snow shoved down your pants by your big brother is yet another thing. (The Eskimo word for that is the same as ours: asshole.) So, one criterion for distinguishing between types of snow is movement, a distinction we don’t normally make often enough to create separate words for it.

I need to learn to make different distinctions in fashion, and to do that I need to create a list of criteria by which to do so. Obviously, many people choose styles largely because they’re popular. That’s one question I have about plain-front pants — did Catherine want me to wear them just because they’re more popular, or is there some other criterion I’m not aware of yet?

Knowing her, there has to be more to it than just popularity. One thing that occurs to me is that human beings need variety. To some degree, car styles of the present are objectively better than styles of the 1960s because they’re more aerodynamic, which saves more fuel, which helps us use less oil, which helps keep us out of wars in the Middle East. Hmmm. Well, I guess car designers can do only so much about foreign policy when Christian fundamentalists are determined to start World War III because killing Arabs will cause Jesus to come back sooner. But not all fashions in car design can be attributed to aerodynamics. Some aspects of car design change just because so many people like significant changes in their environment every now and then. It’s the same impulse that causes us to rearrange our furniture every few years. So maybe plain fronts are not objectively better but nonetheless more desirable just because pleats were the dominant fashion for so long, and maybe 30 years from now some fashion bumpkin will get a girlfriend who convinces him to switch to pleats because plain fronts are so old-fashioned and he’ll start a blog about it. OMG maybe that will be me in my next incarnation.

So, popularity is just one criterion. There must be many more, such as color, proportion, type of material, and so on. Figuring this part out calls for list-making, something else I’m very good at, like I’m good creating categories out of masses of undifferentiated information like the kid on the X-Files.

Values: Deciding What Choices to Make

After I build a list of criteria by which to evaluate fashions and I’m able to make finer distinctions, the second thing to think about will be which distinctions I care to make. I may learn to make certain distinctions only to disregard those distinctions after all because they aren’t useful to me. Maybe I’ll end up deciding that I don’t care to distinguish between snow on the ground and snow in the air, but I will want to continue distinguishing between snow being pulled to the earth by gravity and snow being pushed down my pants by my big brother. That would be because I value physical comfort, and making that distinction might help me avoid my big brother, a constant source of physical discomfort. But maybe I don’t do anything that makes the distinction between snow on the ground and snow in the air useful to me. Maybe the one word snow will continue to serve me just fine when describing both those things.

If I were dictator for life, all offices would have to be this beautiful.

I probably won’t end up thinking about fashion the way D&G customers do unless I’m blinded on the road to Damascus by the sky-god, so what is the set of criteria that makes the most sense to me? Who knows, after I learn why people make a distinction between pleats and plain fronts, maybe I’ll end up deciding that I don’t care to make that distinction anymore. (Please don’t tell Catherine I said that.) In life in general, I value truth and beauty, so when I come to the subject of fashion, I want to figure out how my fashion choices can be more truthful and cause me to experience more beauty. For me, in the context of fashion, “truthful” means that my outer appearance reflects my inner character. Beauty is something I feel, and it’s like a wave of sensuality and intellectual insight all mixed together in one indivisible experience. I live for beauty. I want to see it everywhere. Offices should be as beautiful as cathedrals. I understand why I haven’t thought about fashion until now, but still, it kind of surprises me.

When I investigate subjects for the first time, I always begin with encyclopedia articles. They draw the landscape of an area, and that’s incredibly helpful for exploring it. It’s like cresting a ridge while hiking and stopping to study the lay of the land. Later, when you’re in the middle of a forest and you can’t see more than 20 yards ahead of you, you still have a sense of where you are. You know you shouldn’t accept a mediocre camping ground when there’s a beautiful lake another hour ahead of you. After some encyclopedia articles, I’ll have a better sense of the fashion landscape, and I will be better able to avoid fashions that don’t suit me because I’ll know what all the major options are. I’m reading articles in Encyclopaedia Britannica, Wikipedia, and The Internet Encyclopedia of Philosophy on the philosophy of art, the history of clothing, and the history of fashion. I’ve also read the first chapter of Men’s Style: The Thinking Man’s Guide to Dress by Russell Smith. I’m going to begin writing about ideas in these articles that have sparked interesting thoughts about criteria for evaluating fashions.

A Note on How Often I’ll Be Posting

It makes me sad that it’s been a whole month since I’ve last posted. I love writing this blog and am committed to it. The last month a combination of work, long illness, and vacation made it extremely difficult to find time to write. I’m now going to give myself deadlines: I will try to post twice a month, on the 15th and the 30th. So check back here by August 15 for the next post.

Don’t forget, the most efficient way to keep up with this or any blog is to set up an RSS feed. If you know how to set up a feed, use the RSS icon on the right side of the location bar to get the feed. If you aren’t familiar with RSS feeds, they work just like email. Instead of your email program checking for new mail, an RSS reader checks for new blog posts. But you don’t use the regular URL, you use a special URL. For a good introduction to RSS, check this CNET page.

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.

I think the guy in the first row actually likes wearing his uniform.

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

Click to see a full-sized image of the headquarters of AskMen.com.

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.

Oscar Wilde thought about truth and beauty; let’s see what he has to say: “Fashion is a form of ugliness so intolerable that we have to alter it every six months.” And: “Does this jacket make me look fat?”

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.

Giorgio Armani: “Clothing is the outward expression of the inner person.”

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.

Fashion began when Eve asked Adam: “Honey, does this fig leaf make me look fat?”

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.

Socrates on fashion: “Know thyself. Hey, does this toga make me look fat?”

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.

Don’t believe I’m a nerd? This is me at age 12.

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. [↩]