"The Preppy North" - My life imagined as a catalogue.

I grew up in Connecticut and summered on the east end of Long Island. I went to tennis camp, sailing camp and I took my first steps in Sperry Topsiders. My polo shirts had alligators or ponies on them and my pants were held up by belts with embroidered marine flags or lobsters. I wore tennis sweaters and J. Crew anoraks. My closet overflowed with rugby shirts, plaid everything and as many camp mocs or bluchers that LL Bean could make. Khakis, a navy blazer and bow ties. I was preppy. To a fault.

This is me growing up in the 80's...my style was bold and unmistakable.  Timeless and classic,  I wore it well. — This is me growing up in the 80's...my style was bold and unmistakable. Timeless and classic, I wore it well.

To some degree, where you live informs your style. Where I lived on the East Coast, the general style there was preppy (polo shirts, seersucker and boat shoes) — so I mapped to that, but to an extreme degree. In high school I would rip out pages from the J. Crew catalog and try to replicate the exact look on page 57, 63 or 71. Down to details like wool rag socks or the braided leather belt.

This photo was taken Junior year of high school.  I styled this outfit exactly out of the J. Crew catalog.  Cotton Tee, Chambray shirt and Rugby shirt layered over it.  The pants were "Stone" colored.  The hiking boots were LL Be… — This photo was taken Junior year of high school. I styled this outfit exactly out of the J. Crew catalog. Cotton Tee, Chambray shirt and Rugby shirt layered over it. The pants were "Stone" colored. The hiking boots were LL Bean. And I WAS wearing a braided leather belt.

Looking back on it, it wasn’t just about the clothes, how I looked or how I put them together. I felt like if I could wear what those guys wore on the pages of catalogs, I would be popular or well liked. I would fit in; because I didn’t always fit in. I was a young gay boy in a town dominated by straight businessmen, doctors and lawyers. I didn’t feel like I was like them, and yet, I tried to look like them. I always needed the outsides to look good; it was my attempt to control people’s perceptions of me.

So being an extreme prepster wasn’t just a result of where I grew up, it was a rule of thumb I followed closely to fit in. To blend.

Greenwich High School pics (from L to R): Sophomore (1994), Junior (1995) and Senior (1996). — Greenwich High School pics (from L to R): Sophomore (1994), Junior (1995) and Senior (1996).

Now a grown man, twenty some years later, I’m still very preppy in my own way. My style is not divisive or overly intentional—I’m not mapping my outfits to a catalog page anymore. As I grew into my own person, owned my sexuality and allowed myself to be me, I’ve learned what I truly love about my personal style. And that still happens to be plaid everything, belts with nautical insignia on them, ponies on collared shirts and a good classic boat shoe.

August 2017.  J. Crew, Sperry + Brooks Brothers. — August 2017. J. Crew, Sperry + Brooks Brothers.

My general uniform is still the same, but the guy in the clothes has emotionally grown up to fill them out. I also know that no amount of dressing up or dressing down will control anyone’s perceptions of me. I see personal style as a way to identify myself and adorn the person who I’ve grown to love on the inside. My clothes are not just window dressing for a shell of a person trying to be like everyone else.

Recently, I’ve been further exploring my creativity for fashion, styling and photography by pulling together photoshoots for my blog and Instagram. I started researching preppy culture online and it seems that many people are dressing overly preppy to a fault, just like I did. It’s a whole lifestyle that people subscribe to, as if life is a Ralph Lauren ad. On Pinterest or Instagram, preppy culture is fetishized. Homage is paid to WASPy haunts like Country Clubs, Nantucket, Maine, Charleston, vintage autos, tailgating at The Hunt (if you know what that is, you’re preppy) and anything that looks remotely Town & Country. Perhaps other people’s reasons for self-portrayal in this vein are slightly different than my high school experience in the 90’s. None the less, the extreme preppy movement continues to grow.

It gave me an idea for a photoshoot – why not recreate a sense of living my life as if it’s a catalog. Consider it a clap back to all the preppy accounts on Instagram like @KJP, @SarahKJP or @PreppyNewEnglander. On those accounts you will see lake houses, summer homes in Cape Cod, canoes on top of wood paneled vintage Jeep Wagoneers and a 1980’s Mercedes Convertible and of course golden retrievers. And perfect Hydrangeas…

The first photoshoot I produced and styled, October 2017. "The Preppy North"

Two years ago, I moved from New York City to Minneapolis, Minnesota. My preppy style has evolved somewhat into a hybrid of East Coast Prep meets the Great North of Minnesota. A little less Sperry and a little more Red Wing. A little less J. Crew and a little more Pendleton Wool. I wanted to celebrate that style shift in a more concrete way! In October, I pulled together a small group of friends (@jennaboff, @suzysimon and @lifeofleo), a great photographer Ashley Camper, a styling consultant Emily Baynard and a few amazing local Minnesota Brands, courtesy of Martin Patrick 3 in the North Loop. This is what I call, "The Preppy North" – a day trip to an apple orchard in a Range Rover, a tailgate picnic and frolicking through the orchards. All this, paying homage to an over indulged preppy lifestyle. It was all very intentional, perhaps satirical!

What I really learned from all this is that my love of style doesn’t make me shallow, it makes me creative. And all the hours I spent over the years trying to perfectly replicate a catalog look just so I could feel like I was enough in high school was great practice for producing a photoshoot.

Below are the highlights from the shoot; all photos by Ashley Camper. Click on the image for larger view and you can scroll through. Please let me know what you think in the comments section!

List of brands included at the end of this blog post.