Tyler that is a killer story.
My wardrobe consists of Dickies(shorts,874 Classic and Double Knee Cell Phone pocket), XXL Plain tshirts, vans slip ons(5 pair). If I do go somewhere that would require a more polished look, I have my Dickies collared work shirts.
For the REALLY fancy occasion, I have a Ben Sherman shirt and a pair of Diesel jeans(fake, 20$ at markets).