1. Invest in a good quality knit — you won’t need to throw it away at the end of the season and in a city like New York, it will, no doubt, come in handy as many times as a bottle of water in the desert does.
1a. Eclipse the smart phone, the smart watch, the smart head and invest in a good quality smart shirt. According to PSFK, Ralph Lauren has just launched One not unlike the most recent roll-out from “PoloTech” – a new shirt that will measure the wearer’s vital activity in REAL TIME.
2. Dare to challenge the overarching conformities: if everyone is wearing skinny pants but you like them flared, you’re in the right. Wear them flared.
2a. Don’t smoke.
3. Consider the Canadian Tuxedo, then with the kind of reckless abandon you might find at 2 a.m. at a mini mart near a bar that serves exactly zero Sour Patch Kids, steal it, call it your own and laugh at the notion that it could have first belonged to anyone else. They say good artists copy and great ones steal but the best ones don’t even let you know there was any form of theft involved.
5. Unless you’re not quite feeling like the metropolitan cowboy you have created, which is fine, because you’ve identified three prototypes for the identities you will call your own (American cowboy, American computer wiz, American [motor]cycler,) and in model two what worked for Steve Jobs also works for you. The black turtleneck will never disappoint you unless you disappoint it.
6. On said turtleneck: leave behind one qualm. Thou shalt not hesitate to pair your concealed neck with a pair of ivory pants, regardless of the time of year. If there are rules, they are only the ones you have put in place — no societal structure, especially one contingent on the Gregorian calendar, shall convince you otherwise.
7. Think thematically: one afternoon’s suit (double breasted, nothing less) may very well be another evening’s literal homage to the Old West.
7a. But don’t carry around a gun. Do, however, wear a bullet proof belt.
8. Don’t compromise you. If you never liked taffeta pants, you still don’t like taffeta pants, but everywhere you turn, lo and behold: taffeta pants, don’t give in. You have come this far, you have identified yourself, you have considered what it means to abide by rules that you have set and there is no reason to deviate. Unless, of course, those pants are actually silk faille.
8a. On the rules: If you feel like layering a white shirt under a blue plaid blouse to take a bow after a show that was full of indelible black tie garb, no matter the quality of importance among the people in said room, make like Nike — nay, give Nike a run for its slogan — and just do it.
9. There is no such thing as overdoing what you love: so what if you own fifteen pairs of jeans. Do you wear them all? Case closed.
10. Think about dyeing your hair white. Let this point bubble up from the depths of your internal dialogue at least three times a year.
10a. Retreat to a tropical locale every time your skin begins to feel vaguely pasty.
Everything I know about personal style, I learned from Ralph Lauren.