Vanity Fair has excerpts from various sections of the upcoming book True Prep: It's a Whole New Old World, written by Lisa Birnbach as a sequel to her 1980 bestseller The Official Preppy Handbook. TOPH (a complete scan of which can be found here) was apparently originally intended to be a humour book, but over the years many have adopted it as an earnest guide to creating the ideal preppy lifestyle. Sadly, the book is now significantly outdated, with all its meticulously-researched addresses, phone numbers, and postal rates having become all but useless to the modern reader. Combine that with the recent resurgence in preppy style and the fact that the original is long out of print, and is it any wonder that a sequel should arrive? 

True Prep is essentially conceived as an update of the original, to reflect social changes that have occurred in the last 30 years. For example:

If, in 1980, you had whispered to friends that within the next few decades America would elect a thin, black, preppy, basketball-playing lawyer to be president, they would have laughed at you and exhaled [smoke] in your face, inside the restaurant or club where you were sitting.

Now, contrary to what you might first assume, TOPH wasn't just a style guide, but an insight into an entire way of life, covering not only the "correct" schools, sports, decor and pets, but also delving into more abstract topics, such as attitudes and manners. The excerpts from True Prep show that it contains the same breadth of coverage as the original, discussing not only the pedigree and size of logos on polo shirts—unquestionably a topic of grave concern—but also matters like demographics, career choices, and the importance of frugality.

I'm hugely looking forward to this book. Not having been "to the madras born," as it were, it's hard enough to understand true prep even with the assistance of TOPH, let alone trying to figure out what it means to be preppy in 2010 rather than in the '80s. But of course, as this is a style blog, I'm most looking forward to their thoughts on changes in preppy clothing, particularly those "recent prep brands we are forced to recognize." What are the fates of J.Crew and Ralph Lauren? Inquiring minds want to know! And I, for one, am placing my pre-order ASAP.

I'll leave you with a True Prep Preppy Playlist, courtesy of publisher Knopf Doubleday.

Let me explain. For a long time, I thought very poorly of men who wore pink shirts. To me, it just screamed "LOOK AT ME! LOOK HOW SECURE IN MY MASCULINITY I AM, FOR I AM WEARING A SHIRT IN A STEREOTYPICALLY FEMININE COLOUR!" I never even thought pink was a colour that looked particularly good on men; it seemed like a man would only wear it if he had something to prove. Also, it didn't help that the only pink shirts I had ever seen were either (a) dress shirts worn by greasy Gino/Eurotrash types—the types who would also wear iridescent ties and white square-toed loafers—or (b) polo shirts with the collars popped. In other words, only douchebags wore pink shirts. What's more, once I started to become more fashion-conscious, I realized that pink dress shirts were a fad, and I knew that those men would look back in 20 years at pictures of themselves and shake their heads at how ridiculous they looked.

But all those preconceptions changed when I started learning about preppy style. I realized that pink shirts weren't a fad; they had, in fact, been worn for decades by men who were extremely traditional. Actually, I should qualify that: pink dress shirts are, indeed, a fad. But polo shirts and oxford shirts, made by the likes of Lacoste and Brooks Brothers, had been popular in pink since well before 1980, when Lisa Birnbach published The Official Preppy Handbook. As she wrote at page 141:

The classic shirt is the Brooks Brothers button-down all-cotton oxford cloth shirt. Pink is the most famous color, and it is widely supposed that no one except Brooks has ever been able to achieve that perfect pink or that perfect roll to the collar.

Christian Chensvold, of the blog Ivy Style, traced the phenomenon in greater detail in an article for The Rake magazine:

Like the white flannels of the English gentleman, colorful sportswear signals the wearer is at play, not work. Easily soiled, the clothing is thus impractical, making it a symbol of both conspicuous consumption and conspicuous leisure. “Navy blue aside,” notes Paul Fussell in “Class,” his 1983 classic on the American status system, “colors are classier the more pastel or faded.”

“You wouldn’t have someone not from money walking around in clothing that would draw a lot of attention to himself,” explains [author and custom clothier Alan] Flusser. “Up to the ’60s it was always a brahmin, upper-class thing, because they could wear it and not be laughed at.” For Flusser, the postwar starting point of the look is Brooks Brothers’ celebrated pink oxford-cloth buttondown. “Pink symbolizes this whole subject matter,” he says. “Imagine a guy wearing a pink shirt: If people didn’t understand what that was about, you had to be prepared to be laughed at.”

“When my brother was at Harvard,” Flusser continues, “the kids were wearing blazers and red or yellow pants and would always use color in some sort of interesting way. There was a sense of who could wear the most outrageous tattersall vest. But being able to wear that kind of clothing comes from a certain lineage where you felt, ‘This is what we do, and if people don’t understand it, they don’t understand it.’”

So all it took for me to change my attitude completely towards this particular garment was to change my mental association from negative to positive. Pink shirts—polos and oxfords, anyway—were no longer douchey; they were preppy. I didn't want to be douchey; I did want to be preppy (essentially because of the associations recounted above by Chensvold, as well as others on which I'll be expanding in a future post). The conclusion was simple and obvious: pink shirts are good. So when I had the opportunity recently to acquire a Ralph Lauren polo shirt in the staple "Carmel Pink" shade for less than $20, I jumped at it. I wore it today—the first time I had ever worn a pink shirt. I wore it with lime green shorts, and then out to dinner with white linen pants and navy boat shoes. And, though you might say it's bull, I felt like a Brahmin.

I like to think that I'll look back on 2010 as my "Summer of Prep," the year that I finally came home to the style that suits me best, and towards which I've always tended to gravitate. You see, throughout my teen and young adult years, my casual summer wardrobe was fairly uninspired. I always had summer jobs, so I was focused on work clothes. (Perhaps it's fortunate that I haven't bought many summer clothes until now; it's taken me this long to figure out how they should fit!) This year, though, I haven't been working for most of the summer, so I seized the opportunity to expand my wardrobe with colourful shorts, polo shirts, boat shoes, and ribbon belts—all those perfect preppy staples.

In the process, I've really started to become a fan of Brooks Brothers. Not really in terms of wearing the merchandise, since their sizing tends to be problematic for me and it's hard to get the stuff in Canada, so much as in admiring their aesthetic. I love how they manage to be both timeless and of-the-moment, while infusing their clothes with more colour and vibrancy than you typically get even from someplace like J. Crew.

Now that fall is peeking around the corner, I'll have the opportunity to think about what prep means for the cooler months. Unquestionably, it means layering, and sweaters galore, particularly cardigans and cable-knits. As far as colours, I'm thinking vibrant orange, chocolate brown, and jewel tones, along with the usual staples of blue, white, and green. I'd say I'm generally a fan of rich, rather than bright, colours for colder weather. I've got a pair of burgundy pants from Club Monaco that I'm itching to break out, which I'll probably wear with brown suede tassel loafers.

And of course, I'm digging the styles showcased in Brooks' Fall Preview 2010. I can safely say that there is nothing there that I wouldn't love to wear. They really do have something for everybody, and I don't think you could go wrong pulling out any or all of those looks to inspire yourself this fall.

In my introductory entry, I suggested that most men should be more aware of the power of their clothes as tools for expressing, and even constructing, their selves. But what if you go too far the other way? What if clothes are all that’s important to you, and you have little or no sense of self outside of the clothes that you own and wear?

To some extent, everyone reflects who they are through the clothes that they wear. It helps you express your individuality and be more in touch with yourself, and it also lets you tell people something about who you are as a person. It only becomes problematic when your sense of self is incomplete. I think this is the position in which teenagers often find themselves. For example, I'll bet just about everybody of my generation knew someone who turned into a goth in high school. Why? Because they were trying to figure out who they were and who they wanted to be, so they were trying on different identities to find one that felt right. The healthy thing to do, I suppose, is to eventually come to a conclusion about who you are, and move forward with your life. But what if you don't?

Suppose you never finished figuring out who you are (or didn't like the person you thought you were becoming), but you had a pretty good idea of who you wanted to be. Well then, you might just fill in the gap with whatever clothes best reflected the ideal person you wished you were. You'd probably also form emotional connections with particular items of clothing, or clothing brands, whose marketing images resonated with the ideal you and your ideal life. If you dreamt of country estates, yachts and trust funds, you might stock your closet with Ralph Lauren and boat shoes; if you wanted to feel sexy and desirable, the centre of attention, maybe you'd splurge at Dolce & Gabbana or quest for the perfect black leather jacket.

Brands, in particular, have a special power, because they can pack a whole array of images and associations and fantasies into one little logo, then conjure them up again instantly whenever you see that logo. That little embroidered polo player, those little embossed initials, are shorthand for every advertisement you've ever seen, every concept and image you've ever known to be associated with that brand. No wonder that fragrances and accessories, the least-expensive products sold by virtually every fashion house, also comprise the majority of their revenue. After all, not everyone can afford $2000 for a Dolce & Gabbana suit, but just about everyone who cares to can afford $60 for a bottle of D&G cologne—to buy into the fantasy.

Everybody does this, of course. Women wear heels and lingerie when they want to feel sexy; for men, maybe it's a flashy new blazer or your favourite (lucky?) clubbing shirt. I know a certain lawyer who always seems to be wearing the same Burberry tie whenever I see him in a photograph. Now, there's a slight element of costume whenever you wear something deliberately to make a particular impression, or to make yourself feel different. It's only a problem if you're wearing that costume all the time, and you get so wrapped up in maintaining your image that you forget—or don't have the headspace—to make time for anything else.

Test yourself, fashionistos: If you were forced to stop shopping and wear a uniform every day, would you still feel like yourself? Or would there suddenly be a gaping hole in your identity? If you really care about clothes, the answer is probably yes... but if you couldn't find something else to care about instead, you may have a problem.

...apart, that is, from the fact that my friends and relatives kept telling me that I should. Because you know, there are already plenty of great blogs out there. Do I really have anything new and valuable to contribute? I mean, I’m not an expert or anything. I don’t work for GQ; I don’t have a standing invitation to Fashion Week; I don’t take pretentious photographs of people posing on cobblestone streets beside vintage bicycles with cigarettes dangling languorously from their fingers and/or lips. And, in spite of the fact that I’m a lawyer, I don’t even have the money to buy all the lovely clothes that I want, because I’m still young and broke. So what have I got to say, really?

I think my answer is the same as a lot of bloggers: I have some things that I feel that I need to say, and I believe that other people might derive some value from hearing them. Despite the fact that my interest is amateur rather than professional, I make it my business to be well-informed; I hate to put forward an opinion about something if I haven’t first taken the trouble to educate myself about it, which hopefully means that people will learn something from me. And—perhaps because of my legal training, but probably because it’s just the kind of person I am—I take a very analytical approach to things, and I always like to know whether there are rules that ought to be followed, and then to help other people learn those rules. The great thing about men’s style is that, although there are rules, they’re not that hard to learn, even though there are a lot of them. And you do need to learn them—learn them well enough to follow them perfectly—before you can even think about bending them.

The other reason I started this blog is because we all have to face one simple truth: Clothes are important, and people judge you by them. I may wear a razor-sharp suit to work every day to impress my clients, while my programmer friend may wear whatever T-shirt happens to be on top of the pile of clean laundry, but every clothing choice that each of us makes tells the world something about us. The people we pass on the street each day don’t know our life stories. Through the things we choose to put on our backs, we influence how those people will perceive us.

As anyone who’s ever taken an English class knows, though, meaning is more often found in the eye of the beholder than in the intention of the creator. One man’s razor-sharp suit is another man’s totem of corporatist hegemony; one woman’s dreadlocks are another woman’s public health nuisance. Hence, the all-important question: Who are you trying to speak to with your clothes, and are they hearing what you want them to hear?

My goal is to make you more aware of the power that your clothes wield—both to express your identity, and indeed, to create it.

Or, to put it simply: Threads count.