Whenever going out on the town, I’ll wear the same black sweater my girlfriend bought me in Italy in 2006 and the same brown pants I found on sale once in 2007. All of the women in my life (girlfriend, mom, grandma) ramble on about my ragged style. So finally on April 1, I went shopping

Upon stepping foot in the mall, I saw it gleaming like a jewel on the strip:  Tommy Bahamas. Everything I’d want in life. Tropical. Casual. Colorful. Cool.

A 78 year old salesmen named Walter greeted me at the entrance.

He helped me with some of the newer Tommy Bahamas styles including pleaded short shorts, button downs with fluttering toucans, and straw beach hats. I loaded up on enough new clothes to last for years (3 shirts, 2 shorts, 1 hat) and arrived for family brunch, excited to sport my new duds.

“Wow you look wahndaful,” my Grandma Evelyn said gleaming proudly at her grandson.

“Very nice,” my mom followed up.

“Are you being serious?” my girlfriend whispered in my ear.

We ate brunch and I enjoyed some furtive glances from some very attractive women in their late 80’s. As we stood to leave, however, I had one of those moments that I call in my book a Now Point. I looked down and saw the pleaded shorts shorts riding high up my crotch, the trick of some sick-in-the-head Tommy Bahamas designer in an office in West Palm. I felt trapped. Trapped in my pleaded short shorts. Trapped in the forward march of time. Trapped in a void of fluttering toucans and tall blond coifs.

*****

Last Fall I was sitting in Dodger Stadium for a baseball game. In walks an obnoxious guy with a bright green sportcoat and giant hair coated in gel. I couldn’t help but think “annoying” “ugly”  “why in front of me?”

But a few seconds later, I found out the guy in the bright jacket was Tre Cool, the drummer in the band Green Day (see above photo). I could care less about Green Day.  But all of the sudden, in my mind, he had permission to be weird. So it goes with style.  Fall into a crevice of doubt and your wardrobe bears the dust of darkness. But ascend a peak of confidence and pleaded short shorts and fluttering toucans form majestic shadows against a rising sun.

Or at least that’s what I heard on Oprah.