Classic Nantucket style is great, but not my personal style. How do I stay location appropriate?

Suddenly I’ve realized that I’m “a fish out of water” because of my bicoastal lifestyle! Each year, my family and I make our annual pilgrimage from Silicon Valley to Nantucket Island, where we visit with our various family members who are lucky enough to call the island home. However, the older that I get, the more and more I seem to run into the same problem.

The classic outfit of a Nantucket vacationer is mainly made up of preppy pastels, madras, and the unmistakable swirl of Lily Pulitzer prints. Since I have been coming to the island, it has only become more and more pronounced, to a point where one would be hard-pressed to find someone who is not indulging in this island style.

Why should you care about my observations on a small island off the coast of Massachusetts? Well, the “vacation dilemma” as I call it has been something that I have been grappling with for a few years now. Since moving to California a few years ago, my personal style has gotten progressively more casual, and I tend to veer towards neutrals and loosely fitting clothing, rather than the pastel preppy alternatives. As I gravitated deeper into my more casual style, I began to find that on Nantucket I felt out of place in many situations. At restaurants, walking around downtown, and even during quick stops in coffee shops, I felt that my clothing was making me feel self-conscious and shy.

Now, I am not advocating for you to abandon your own personal style in favor of whatever trend is currently in fashion. However, at its very best, clothing is supposed to make you feel comfortable, and let your personality shine through past your exterior. And quite frankly, I used to spend my vacation feeling insecure about my clothing choices.

Would you bring your best heels and jewelry to a remote cabin?

Finally, this year I have come to a conclusion. There is such a thing as location appropriate dressing. Think about it. We spend a countless amount of time discussing clothing that is age appropriate, or clothing that is situationally appropriate. You would not wear a crop top in your 60s, no more than you would wear a ball gown to a bookstore. However, we often are so proud of our own personal style that we forget to pay attention to the location appropriateness of our clothing.

Obvious location appropriate qualms aside (i.e., no shorts on a ski mountain), it is important to pay attention to where you are going. If you have been to your destination before, say for instance a family member’s house, or a favorite lake, then you already have an idea of the kind of clothing that you will likely want to wear. However, if you have not been to your destination before, take the time to do some thinking about what may or may not be appropriate. Do you really need to bring a strand of pearls to a remote lake house? Are you sure that you will not deviate from a uniform of jeans and sweatshirts in Carmel?

After you have given an honest appraisal of what situation you are heading into, make sure to have fun with it. Getting dressed and looking your best should be fun, especially when you bend the rules of your traditional style. Personally, this year I took my vacation to Nantucket as an opportunity to break out my white jeans and beaded wedges that I would otherwise glance past in my closet back in California.

By thinking about the location appropriateness of your clothing, whether it be for a vacation or simply for an outing, you will find yourself feeling much more confident in what you are wearing. You also get to have fun with your wardrobe, and get use out of some of your garments that would not otherwise gather dust. After all, isn’t having fun and feeling great what fashion is all about?

About Emma Grillo
:  From a young age, I’d pour over the pages of my mother’s Vogue, and relish any opportunity to dress up for a special occasion. This infatuation with fashion has followed me to Lewis and Clark College, where I am pursuing a BA in English and Art History. I am extremely excited to intern with Joseph, learning the ins and outs of personal branding and style.  I am also writing 10 blogs, including this one. I am thankful for this unprecedented opportunity, and for the hands on education that I will undoubtedly receive.