A Day of Preppiness


Pretty & Preppy… 🙂

This weekend I joined thousands of fellow Washingtonians in attending the 87th edition of the world-famous Virginia Gold Cup steeplechase race.

I enjoyed the beautiful Virginia countryside on a sunny and hot day, sipping bourbon, eating pulled pork burgers, and occasionally betting on a horse or two. But most importantly, since my friends had invited me to their VIP tent, I took the opportunity to immerse myself into the posh “preppiness” that surrounds horse racing events. And I found out that I actually enjoyed it… in my own, humorous way.

The moral of the story for me was an extension of the old adage that everything is good in moderation. Well, being preppy is the opposite of moderation, you might say. True — but when consumed in small doses and with a good sense of humor, being preppy for a few hours can lead to a day well spent in the company of nice people, while getting a bit of suntan and making a buck or two from placing the right bets at the right horse (oh well – you can call it my rookie’s luck, as well, I guess).

My main point here is that a few years ago I would have totally dismissed the idea of attending an event like that one. I would have found dozens of reasons why dressing up in bright colors, helping your date fit her enormously large hat in the car, drinking lots of booze in the scorching sun, while trying to make sense of the ridiculously named horses contesting in the race, would go against my core. But this year, I decided to indulge my curiosity and give the steeplechase a chance. And I had a blast!

Betting on Horse #8 Was a Good Choice! 🙂

For one, seeing so many people dressed in bright (and sometimes ridiculously mismatched) colors is worth millions. Add to that the opportunity to feel like you’ve just traveled back in time and space to the 19th century countryside in England, and the experience begins to become priceless. Then, add the extra bonus of seeing your coworkers or close friends act like inebriated 18-year-old kids, and the attraction to attend the event becomes irresistible. I personally think winning a race (rookie’s luck or not) is just the “icing on the cake,” just the extra benefit of attending so you can pretend in front of your geekier friends that you ran all kinds of statistical analysis in your head so that betting on horse #8 was not a mere coincidence. Speaking of winning horses, look above at a photo of my “golden” horse #8. (And to those who already think I’d made loads of money from my bet, I got $20 — not a big prize, but definitely a good reason to continue the celebration after we got back to the city in the evening.)

In case you want to see some hats extravaganza, look no further than the photo below of my friends. 🙂

Hats Extravaganza

As you can see, we all played the right preppy part in the show, and we all had a good time doing that. So my advise, my good friends, is not to dismiss any opportunity to experience events that may sound or look outlandish to you. Preppiness can be a sign of arrogance, but when done in moderation and with a smile on your face, it can be a sign of a healthy sense of humor. For eight hours on Saturday, we lived in a funny fantasy, pretending to be characters we’ll never be in reality.

Looking at Preppiness from the Humorous Side

Have you recently “walked the walk and talked the talk” at a preppy dress-up event? Care to share some fun experiences (and lessons learned)? 🙂

This entry was posted in Experience and tagged , , . Bookmark the permalink.

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s