The Hipster at the Yacht Club: Dressing the Part

Welcome to another episode of Hipsters v. Prepsters

See what happens this week when tomboy fashionista Chynna Pope takes on a popular preppy trend and makes it her own.

This is a photographic account of one girl maintaining her style and individuality in a world of Lily Pulitzer shift dresses, cable knit cardigans, Jack Rogers sandals, and strings of pearls.

Her bags are packed, and she’s ready to go.


Disclaimer: This is a rental car….I do NOT drive a subaru! …but I do drive a VOLVO

Where did she go to attempt the daring stunt?

The preppy mecca of New England, of course: Martha’s Vineyard

Cape Poge

View of Cape Poge from Chappaquiddick

Now, despite my Beacon Hill roots, I am not a prepster. Conversely, I wouldn’t necessarily label myself a hipster either. The closest label I can come up with for myself is aBeacon Hellion:” One who appreciates tradition, but also likes to stir it up from time to time. You see, I like to dress up. Whether it’s in a dress for The Yacht Club or a pair of ripped jeans and a T-shirt for a dive bar, I always approach getting dressed with the same philosophy: life is just one big costume party! If its the country club crowed I need to schmooze with, fine! I’ll pull together a seemingly conservative ensemble with a little bit of my own sassy flair. The key to dressing for a specific place or occasion, is appreciating and respecting your environment without loosing sight your own individual style.

Here I am taking a stab at “preppy” in this bold printed tunic dress, singed at the waist with a studded belt and a bohemian jingle-jangley bracelet.


…..And, yes, I am wearing Tory Burch sandals. Guilty as Charged. But I don’t care, they are orange patent leather and they go perfectly with this ensemble. Don’t worry; more smelly Chuck Taylors coming soon!

20130716-141753.jpg Dressing for a conservative audience is always a bit of a challenge. The innate restrictions dictated by dress code and expectation push you into unfamiliar territory forcing you to think differently about your wardrobe and approach your closet with a new set of eyes. This process will definitely bring you outside of your fashion comfort zone, but it is totally worth it. Mixing and matching old pieces in new ways is a great exercise in expanding your fashion horizon. If done properly, you may also find yourself creating really great outfits.

Clothing is indeed a great way of expressing yourself. It is most interesting when you have multiple facets to your personality. I view dressing like reincarnation; I shed one ensemble to give life to another persona. This system works for me because I do about 5 activities with 3 different groups of people a day. That kind of social schedule requires quite a few costume changes! My fashion world is forever fluid. In contrast, some people make the mistake of letting clothing define them. They are strongly influenced by their peers, and those around them and get stuck in a comfortable merry-go-round of a specific style. This kind of behavior leads society to label groups solely on their clothes. And it’s true, we really do tend to recognize and categorize various subcultures and groups largely on what they wear. The two groups in question today, Prepsters and Hipsters have assumed iconic uniforms of their own. Prepsters are famously known to wear madras shorts, boat shoes, and pop the collars on their Brooks Brothers oxfords as they sail around Nantucket Sound. While hipsters are usually spotted in decrepit warehouses or artist lofts in up and coming neighborhoods wearing, flannel shirts, skinny jeans, high top chucks, and Supreme hats or beanies. Don’t get me wrong, I see the appeal to both of these subcultures, and I have a lot of each of them in my make up. It is forever my goal to seamlessly mix these two groups in to some sort of super fashion creature that is just too cool and complex to label.

My approach to this project was to take some of my favorite aspects of both groups and mix them together. I thought color and silhouette were good places to start. So, for the preppy side of things I decided to focus on color. Just as we associate the color black with the “Goths,” some color combination shave become synonymous with the prepsters. Maybe pink and green rings a bell? (RIP Lilly Pulitzer) That was a little too extreme and girly for my taste, so I went with another color combo that has recently been very popular both within the preppy community and beyond: PINK and ORANGE. And for the other half, i decided to go with a “grungier” aesthetic with ripped garments and loose flowey tops that hung from my body. These are the outfits that I came up with!

Doing a little Hula dancing on the Ferry after dousing myself in water to keep cool.


Earrings: Jasmin Sola (a million years ago…when it still existed)
Top: Urban Outfitters
Shorts: Paper Denim Cloth
Sweater: Necessary Clothing NYC
Sneakers: Hand Dyed High Top Chuck Taylors (bought in Italy)

A modern take on an old classic. Chynna Pope Couture Pink Tuxedo ensemble for a night out on the town….


Bow Tie, Top and Shorts: Chynna Pope Couture

…and a glass or two of champagne back at the house….

Sweating out a hangover has never looked so chic!


I found this orange sweater in my mom’s closet at the summer home last year…it has been living in my trunk ever since….looks great, but smells a little funky.


top: OSC Sport

Nothing a little salt water, sun and a great swim suit can’t fix!


Suit: Caluna Intimo e Mare (it’s Italian)

Kind of a preppy pattern with a sexy one piece hipster cut.

And, just in case you didn’t get enough of the orange top, and this amazing view….


I’m not really sure which two subcultures I mixed here. Maybe Gypsy pirate and Rap video girl? I Don’t know. In any case, The gold Bathing suit is a good summer neutral. Its simple enough to be worn with a simple tunic top. A look favored by the mummies and Beach Club. Or you can do the whole beach bombshell thing accessorized in body jewelry, lots of tanning oil, and 8″ platform heels. I think I found a happy medium here that was appropriate for the Chappaquiddick Beach Club.


Suit: OndadeMar

Sometimes the best way to mix preppy with hipster, is just to insert your hipster self in to an ultra preppy setting and see what happens. Doing that under the freezing cold water of the outdoor shower just adds to the fun!


Parting Photograph


“Arabesque at the Breech”


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