Originally published in the Men's Health MVP Network, September 2015. Part of the Fall Into Autumn campaign.
The key to fall style is really the key to style, at large, which was given 400 years ago by Billy Shakespeare, and that is "To thine own self be true." I'll add to that "Unless you're an a-hole." But here you are, reading these words, obviously on a quest for knowledge and/or self-improvement, so I think we can safely rule out the latter.
In college, I was a bit of a geek. While all the other guys were at the bar hitting on girls, I was in the library writing their papers. Sure in the beginning they hooked up, but very quickly the girls became bored with those strutting, pompous, Cool Water-drenched, gelled up, proto-metrosexual date rapists. It wasn't long before they got bored and started looking deeper into the mating pool, where they stumbled upon the salt-smooth rock of my focused indifference. Without tooting my horn too much, I'll tell you this: it was irresistible.
I realized I'd stumbled upon an axiomatic truth that would resound across the world of "dudes" and be borne out in the "geek chic" movement so many years later (which totally flew in the face of the original concept): when it comes to "fashion," care less, not more. Pay attention to what you're doing, so long as it's not simply trying to get laid. There's nothing quite as sexy as a guy performing a task, be it fixing a lawn mower to solving a complex logical proof. The combination of drive and purpose coupled with the lack of attention paid to the opposite sex is a most potent elixir of attraction.
Extrapolate this to style: formless, utilitarian, suited to purpose. There's a description of Dean Moriarty from On The Road: "His dirty workclothes clung to him so gracefully, as though you couldn't buy a better fit from a custom tailor but only earn it from the Natural Tailor of Natural Joy, as Dean had, in his stresses." I always held onto that quote, and it has always informed my style — suited to task, or the exigencies of the day. No unnecessary adornments or embellishments. Perhaps a scarf if there's a chill in the air.
Autumn is a wonderful time for this fashion non-statement. A time of reflection, of passage — the sloughing off of the blithe indifference of summer and a reinstatement of manly purpose. Layers. Topcoats. No more short pants. Something with a high thread count to protect against the burrs and snares of rotting nature. Sturdy denim or khakis. Cardigans, unless you work with heavy machinery, in which case something more form-fitting. Nothing can ruin a season like getting sucked into a combine by a dainty ascot.
As a writer, I have pretty wide latitude as dress goes. Usually it's what's closest to my computer that I wear, if anything at all. But then in order to write, one must force themselves into the world — hunting, gathering experiences that will be melded into stories. The autumn time is a great time for traditional writer style — sport coats with elbow pads over sweaters over button downs over tee shirts. Khakis, corduroys, cardigans. Perhaps, as with John Steinbeck, a sailor's cap. Hunter Thompson was a man of high personal style. Did he shop the J. Crew catalog to achieve that look? No. Chances are his outfit was a conglomeration of gifts given by Hell's Angels, or Hawaiian shirts he woke up in, not knowing when or how he donned them in the first place, and often several zipcodes from his bed.
Unless you're at a formal event with a specific dress code, I think the closer you keep your garments to the person whose genitals they are covering, the better you will look, and the better you will feel.
People may judge a book by the cover, but they stay for the pages between.