Now that I am retired, I am a t-shirt wearing guy. When I worked in the Grace Building in Manhattan for Northwestern Mutual Financial Network, I was required to wear a suit every day. In the Hamptons, it's informal for almost everything, so I wear a lot of t-shirts.
I have a habit of buying cool t-shirts from places I love or amazing tourist places I have visited in Europe, or a National Park or a ski area. When I wear them, I feel part of the magic of that trip.
Now that I am sixty-something, I have about two full trunks of t-shirts, all relatively brand new, so I can't just get rid of them. My wife is tolerant to a point, thus the two trunks. Every summer I seem to favor about five or six "go-to" t-shirts. Many of my go-to t-shirts are my Hamptons t-shirts.
I have t-shirts from a few of the local beaches like Atlantic
Beach, a few of the now out of business restaurants like Cyril's. I have t-shirts that were gifted to me from the places I wrote for like Dan's Papers, Montauk Pioneer,
Patch and Hamptons.com. I haver t-shirts from the places I sail to like Greenport, Sag Harbor, Orient Point, and Shelter Island. Then I have those participation t-shirts well-earned in local bike rides and 5K/10K runs. I just have way too many t-shirts.
Everybody has to have a favorite go-to t-shirt for daily chores and that easy breezy casual feeling of just feeling relaxed. I really don't enjoy wearing new t-shirts but prefer older ones that are faded, worn, and soft.
This last summer my go-to t-shirts were a combo of something old and something new. I fancied a new Verbier Switzerland blue one and a 10-plus years old grey South Ferry (Shelter Island) along with a few 3 Mile Harbor t-shirts that have a chest pocket! Once a week I wear a white Cyril's he actually gave me for free and a grey Nancy Atlas
t-shirt that I bought from her mom at the gazebo in Montauk the year her oldest son was born. Somehow those where the ones that were on the top of the t-shirt trunk.
I have an East Hampton Indoor Tennis
t-shirt that I wear when playing tennis, but amazingly 2019 I never played tennis, a sport I once spent 25 years of my life playing almost 5 days a week all year round.
I have a Ditch Plains
shirt I purchased the day before I moved out of Montauk for half price. I even have a custom t-shirt created by Jimmy Giles of all the Montauk bars Jimmy Giles was bartender at and was fired!
There are a few Hampton's t-shirts that I was given at events I covered that to this day I don't understand the art work on them, but I still have them.
When I wonder what is my all-time favorite Hamptons t-shirt it has to be my Blue Parrot work t-shirt from around 2004 and designed by both Sarabelle Prince, and Roland Eisenberg.
My oldest t-shirt is one from Madison Hut in the White Mountains that I bought when my daughters and I slept there on a four days daughters/fathers Mt. Washington climb hike.
To me, old t-shirts are like photographs with great memories that you proudly wear. I am sure I am not alone on this.