The Perverse Prepster


Up until the early 2000s, men’s fashion and style was a largely monolithic affair.

When Casual Friday launched in the 80’s, professional men were terrified of “getting it wrong”. Driven by fear, they bought whatever they could find. Hence, the tragic combination of baggy khakis, golf shirts, and white socks.

From the fashion travesties of the late 20th century arose the metrosexual. They deserve credit for self-expression, but none of us miss prodigious man jewelry or man bags.

With the introduction of social media, everything changed.

With so many more eyes upon men’s style choices, the fear of “getting it wrong” reared its ugly head again. This time, men didn’t buy whatever they could find — they just tried to get better at it.

Men’s fashion has split off into several tribes, each of them encapsulating a different set of tastes and lifestyles. Let’s just call these camps the Perverse Prepster, the Arty Ninja, the Dedicated Follower of Satin, the Statham, and the Schlub.

Here at Tailor Vintage, we’re partial to the Perverse Prepster. It’s an adventurous take on preppy style. Let’s break it down and figure out if this is the right style for you.

The Details...

When your typical prepster tries to stand out, it’s pretty half-assed. A brightly colored watch strap or oddly patterned socks is usually as far as they’ll go. Next to the Perverse Prepster, those efforts just look amateurish.

Where your typical prepster will trade out Oxfords for tasteful white sneakers, the Perverse Prepster will opt for that same pair in gold.

Where your typical prepster opts for classic, round sunglasses, the Perverse Prepster wears a contemporary pair with brightly colored frames.

Where your typical prepster keeps their face clean-shaven, the Perverse Prepster will lets beard grow until they look like a classed-up lumbersexual.

In short, the Perverse Prepster wears the typical preppy garb: button-ups, chinos, Oxfords, and a nice sports jacket. However, they strive to take it up several notches. Their goal isn’t just to look classy, but to stand out.

Who’s Doing It?

Former Hipsters

Many Millennials fall into the Perverse Prepster category. The majority of Millennials are now in their adult years, and while they were teens, they were hipsters. Plaid shirts, fitted jeans, and chukka boots are just a few steps away from the prepster style. Given that this generation is known for doing things their own way, it’s no surprise that Millennial prepsters are reinventing the style.

Career-Oriented Millennials

Style has always been a way for men and women to set themselves apart at work. One sure-fired way to quickly communicate your ability to think outside the box is to appear to conform, only to throw in a jarring element here and there. It’s no wonder this style is a favorite for career-oriented Millennials.

Parting Words

This look can be hard to pull off, since it requires a detail-oriented sense of style, a certain amount of creativity, and plenty of guts. Done right, though, it will set you apart in all the right ways.

Ready to learn more about turning your preppy style in an outstanding contemporary statement? Well of course you are.


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