Finding my inner prep

I came of age in the 80s and hated it. Not the coming of age part. Well, not more than anyone hates that awful, awkward time between childhood and being an adult. What I hated were the 1980s. Growing up in the shadow of the generation that had done everything, rebelled against everything, written every good song and made every good movie, I was left with a crappy decade. A decade that tried, and failed, to be cool. And what I really hated about the 80s was preppy clothes.

I went to a WASP, upper/middle-class high school. My family were not WASPs and not upper/middle-class. We didn’t drive a beemer or own a cottage. I simply didn’t fit in. The clothes the other kids wore were like a symbol of how rich and white they were and I wasn’t. The popped-collar polo shirts, the needlepoint belts, the crew neck sweaters and the boat shoes. The khaki pants, the repp ties, the button-down shirts and the penny loafers. With pennies in them. I hated it all.

From the 1960s photo book “Take Ivy.”

What I didn’t know at the time was that this was not an 80s fashion invention. What we called “preppy” was actually a trendy appropriation of the much older Ivy League look. It was also aspirational, and had been for some time. But those 80s kids weren’t in a prep school and did not and would not attend Ivy League universities or belong to the Eastern Establishment. But they wanted to look like they did.

I didn’t. As a non-WASP, working class kid, I couldn’t. Every time I went to school and saw sweaters tied jauntily over shoulders, it was a reminder that my dad drove a Kcar and worked two jobs – as a warehouse manager during the day and cleaning office buildings in the evening. I sometimes had to join my dad at his second job, vacuuming around big oak desks covered in framed family photos. Every smiling person in those photos wearing preppy clothes.

Last week, a courier truck pulled up in front of my house. The driver disappeared for a few minutes into the back, then emerged with a large cardboard box. He made his way up the walk to my door. I signed for the box then opened it like a kid on Christmas morning who, despite knowing what’s inside because he peeled back a bit of wrapper the night before, still wants to play with his new toy. I opened the box and pulled out a pair of tan leather penny loafers.

The penny loafers are not my first piece of “preppy” clothes. In fact, they are the latest in a long line. But they are the item I had the most trouble acquiring. Not because they were hard to find, but because they feel so charged with that old hatred of my 80s teenhood. But as the culmination of building my adult wardrobe, with a very strong thread of Ivy League, they were the one item I was missing.

How did I get over it? How did I find my inner prep? How am I able to look myself in the mirror, decked out in a Shetland sweater, chinos and Bean Boots, and not feel revolted? A search for authenticity. When I went back, past the current and 80s trends for preppy clothes, I discovered a history rich in context, meaning and elegance.

Many people associate the button-down collar with stuffy, drab business-wear. Even the term “button-down” is a synonym for “straight-laced and conservative.” But over one hundred years ago, the button-down was revolutionary and youthful. It had come out of the sport of polo. One of the Brooks Brothers family was visiting the UK from America and watched a polo match. He noticed that the players all had their long, soft collars buttoned to their shirts. They did this, he found out, to keep them from flapping around during games. John Brooks thought they looked dashing. When he returned to the US, his company unveiled a new, sporty shirt that was wholeheartedly taken up by young Americans. It evoked the spirit of the country at the time: rooted in the old-world, but challenging convention at every turn. Some Europeans, even to this day, find it inappropriate to wear a button-down shirt with a suit because they see it as too casual and too sporty. But Americans loved the dichotomy that suggested an iconoclastic and relaxed attitude to dressing.

My custom button-down shirt, navy blazer and old school tie.

And that’s the root of the Ivy League look: introducing relaxed and sporty clothes into more formal situations like schools and the office. Through the 20s to the 50s, students on campuses all around the US, not just at Ivy League schools, were the vanguard of menswear. They started wearing Fair Isle sweaters and tweeds from Scottish country life in the city and at school. They challenged the norms of footwear by wearing slip on loafers. But again, these were an appropriation. One of the first companies to produce the dress loafer, Bass, named them “Weejuns” because they were based on Norwegian workingman’s footwear. Another prep staple, the boat shoe, was created, originally, for boating. The sticky, rubber sole was developed to keep from slipping on the slick, lacquered surfaces of boats.

As practical as the look was, even at the time, there was an aspirational aspect to Ivy League. These upper/middle-class Americans were trying to look like rich British lords or sportsmen. And there developed this idea that clothes that were more relaxed, even a bit shleppy, suggested a nonchalance that spoke of money, especially old money. After all, it was a thoroughly middle-class obsession to be concerned with new clothes in perfect condition. If your shirt collar started to fray or your jacket elbows needed patching, that proved that you had been dressing like this for years. In fact, when the Ivy look started to become a national trend in the 60s, some students even used sandpaper to fray the collars of their oxford cloth button-downs to give them that warn-in, causal air. The pre-torn jeans of their day.

“…to be careless in dress and manner required more confidence than to be careful.”
— Winter Dreams, F. Scott Fitzgerald

And this approach, this nonchalance and relaxed formality is why I was drawn to Ivy League, despite my personal demons. When I started dressing well, I was not interested in trends or forward fashion. I started dressing well as part of finding a new foundation in my life, so I wanted clothes that were classic and established. I was first drawn to Savile Row and the traditional English cut. But as I delved more and more into menswear history, it all kept circling back to Ivy League. And for good reason. As social critic John Sedgwick said “fashion has no place in the Ivy League wardrobe. The Ivy Leaguer is really buying an ethic in his clothing choices [ …] a puritanical anti-fashion conviction that classic garments should continue in the contemporary wardrobe like a college’s well-established and unquestioned curriculum.” (That said, there’s a fair amount of every college curriculum that should be questioned.)

I started my foray into trad clothes slowly, still wary of their 80s connotations. Tweed was an easy addition because it was truly classic, not so much a part of the recent preppy trends. A button-down shirt was a tougher addition. I could not bring myself to get a Ralph Lauren version, that tiny polo player on the front mocking my younger self. So, after much research, I went with the original: the Brooks Brothers OCBD. To be fair, Brooks Brothers does not make the shirts like they used to – the collars are shorter, have a lining, are missing the locker loop and extra button on the back. But there is still something iconic about this shirt and as the years have gone on – I’ve worn mine for about three – the way the shirt ages is a big part of its allure. It is softer, more form fitting. The fraying at the collar and cuffs adds character.

My Brooks Brothers oxford cloth button-down, just starting to fray.

After the OCBD, the rest of the wardrobe seemed to flow naturally. The knit ties, the polo shirts, the grey flannel pants, the softly structured, single vent blazer. Footwear was still a challenge, however. I struggled for years with the idea of boat shoes. Again, they are so iconic, so symbolic. But again, I looked back, past the 80s for my inspiration. So I try to use them only for summer pursuits, especially if I’m on or close to water.

My well-worn LL Bean boat shoes.

I suppose there is a general lesson in personal style here as well. Trying to understand the history and purpose of clothes, and wear them as close to that original meaning as possible, can free you from the whims of fashion. It gives you a grounding, a solid foundation on which to stand when making wardrobe choices. The button-down collar is essentially sporty and casual, so I wear it under a sweater or with an odd jacket and tie. I’d never wear boat shoes with something dressy, but penny loafers can cross that divide.

Pennies from the year my son was born.

There must have been dollars worth of pennies moving through my school, just an inch off the ground. Even though the penny is almost worthless in itself, it still felt like a show of wealth. Wealth my family didn’t have. And while I now embrace the Ivy League approach to style, I actively shun that attempt to dominate others by the way I am dressed. I do not wear penny loafers to put on airs, to show off wealth and privilege. Instead, I’m inspired by history. How a Norwegian work shoe was appropriated, dressed up slightly and used with a suit. How, understanding style and elegance, shoemakers at the time added quality leather and a sleeker, refined design. And how teenagers kept pennies in them for emergency phone calls.

That last bit is most likely apocryphal phooey, but it sounds nice.

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