Today’s wardrobe: pinstripe suit, striped shirt, rep (diagonally striped) tie. That’s right, triple stripage.

I’ve been doing this intermittently, venturing into the dangerous three-pattern mixing zone. According to Lisa Cunningham, board member of the Association of Image Consultants International, “it takes talent, great skill, and confidence to pull this off. But it makes a very strong, very fashion-forward statement.”

And, amazingly, I’m pretty sure my three stripe approach is actually working. I’ve pulled a few compliments and have yet to hear anyone snickering loudly as I pass. Next time, I’ll be kicking it up a notch by wearing striped boxers as well.

Bought a new blazer – three button, double vented, super 120. Horn buttons rather than “ahoy there, I’m a sea cap’n!” gold. The most recent step in my grand wardrobe overhaul. If I’m going to be a young tech/media mogul, I’d damn better dress the part.

I had kickboxing this morning and, per usual, brought work clothes along in a bag. Also as per usual, I forgot my shoes. Actually, it isn’t always shoes – more often, I’ve left out a tie or belt, or I’m one sock short. The root of the problem, essentially, is that I pack my work clothes earlier the same morning, and I have about five minutes from the buzzer to dress, pack and make it out the door. Sure, I could load up the bag the evening before, or even set my alarm clock five minutes earlier for a more leisurely pace. But the night before each training session, I’m convinced there’s no need; this will be the one where I finally remember everything.

None the less, I therefore was forced to wear sneakers to work. Nike cross-trainers, largely used indoors, and still fairly new. In short, fluorescent. There are few things that look worse than a guy in a suit wearing sneakers, except, perhaps, a guy in a suit wearing brilliantly white sneakers. And, of course, I had picked this very morning to schedule a number of important meetings and a business lunch. Helpful tip: Wearing sneakers with your suit into pricey Japanese restaurants is a surefire way to get hidden away in a back room at the really bad tables.

The venerable Wall St. Journal reports on men wearing pantyhose (not cross-dressers, just guys who appreciate the warmth or support that stockings provide) prompting several readers to comment on the Journal’s sinking story standards. Of course, the Journal’s story standards have been sinking for a while – about two years ago, I was the first person to be quoted on their pages using the phrase “wet their pants.” My mother was so proud.

A man’s appearance speaks volumes – his hair particularly so (observe Brad Pitt’s transition from crazy pansy in 12 Monkeys to crazy badass in Fight Club). Thus the importance of Howard Spent’s Interactive Semiotics of Hair. What is your hair saying?