My Sperry Debacle

The worst feeling is starting your week off with a dilemma. Not just a dilemma, but a dilemma that will haunt you and poison your insecurities at least for the remaining days in the week.

This morning was gorgeous at Holy Cross. My twitter was already abuzz regarding the warm weather finally reaching the northeast and how people were eager to put away their sweatshirts and North Faces and put on their summer shorts and Sperry boat shoes.

There it was. It was a subtle as a soft green J Crew polo shirt (I would be seeing later in the day), but to me as emphatic as a “LOUD” orange pair of shorts (I would see later in the day).

To Sperry or not to Sperry…an indirect shout out to all possible future English majors.

I had watched my dad’s pair of Sperry boat shoes slowly experience the typical Sperry “wear and tear” throughout my life and I knew that I wanted a pair of my own; however, getting a pair of Sperrys was a privilege. Well, on my birthday I was finally given my own pair.

My reaction wasn’t the same as the kid who opened the NINTENDO 64, but I knew that this gift was the equivalent of a 13 year old boy’s barmitzfah. I had become a man with my new pair of Sperrys.

After a long cold winter, with limited “Sperry Days,” otherwise known as days where it is sunny, warm, and there is no snow on the ground, today marked one of the first inaugural Sperry Days.

I panicked. I wasn’t ready for it. My reaction was similar to the kid who “chickens out” on jumping off of the high dive into the pool. I wanted to make the jump, but I got scared. I didn’t know if I could “pull off” the new look. Wearing Sperrys as opposed to my Nike Air Maxs is the equivalent of speaking French in a hibachi restaurant. The two just don’t mix, so I was torn with the difficult non-academic decision that started my week.

The Sperry tweets were a call out to me, and I proved that I wasn’t ready to “make the leap.” I wasn’t the man I thought I was when I first received the shoes. So the question will continue to haunt me at least for the rest of the week to Sperry or not to Sperry…

This entry was posted on Monday, April 11th, 2011 at 10:18 pm and is filed under Uncategorized. You can follow any responses to this entry through the RSS 2.0 feed. Both comments and pings are currently closed.

Comments are closed.