Michael Anton, whom I've met several times through a mutual friend, wrote a
book on men's fashion that drew its inspiration from
Machiavelli's philosophy. Now Anton, I note, is
much more inclined to fashionable attire than I am myself. I am however inclined to philosophy, and I realize on reflection that he has a model that with a slight adjustment proves to be much more broadly applicable. With this one small adjustment, it becomes a unified theory for dressing well as a man.
In entirely too brief a summary, Anton suggests that men's fashion (at least for the DC/NYC types such as himself) is a continuum with two poles: the ultra-conservative pole of strict propriety, and the fop. At the one pole is the charcoal grey suit with a white Oxford shirt and a tie that is red, blue, or a mixture of neutral colors that includes charcoal; it should be knotted according to your neck, with those who have long and thin necks wearing Full Windsor knots and those with short thick necks wearing four-in-hands. The foppish pole includes potentially very wild variations, up to and including purple suits and ostrich feathers.
The goal, according to Anton's theory, is to get as close to the foppish pole as you can without looking ridiculous. By remaining rooted in a continuum that traces to the conservative, you can add variations until you get as far away as possible without looking like you are wearing a pimp costume from a 70s exploitation film. In this way you will have an attire that is striking, bold, and develops an internal confidence. If you go too far, you will be a laughingstock. Yet by going as far as possible, you will develop a personal style that is unique and demonstrative.
Now on this base model, different people can go more-or-less far on the scale. A big muscular man can probably wear a purple suit if he wants without anyone laughing at him. One sufficiently physically terrifying can wear broad stripes and carry a skull-tipped walking stick. A weaker man may wish to add only one or two flamboyant touches, but even he should not adhere to the perfectly conservative.
What occurs to me is that this model can be usefully varied by varying the poles. For example, you can hold the one pole steady at conservatism, and replace the fop with the cowboy. Years ago now -- 2004 -- I attended a fundraiser at the
Cosmos Club in DC in such an outfit: a charcoal grey suit, but a gambler's vest, cowboy boots, and a bolo tie.
I had never heard of the Cosmos Club. The email invitation I got mentioned the address of the place, and the name, but nothing more about it. Emailed invitations are particularly informal; this one came from a US Marine, for a time after business hours; and it was at a place called a "club." So, naturally I assumed it was a bar of some sort.
It happened that I had another engagement in town that required semiformal dress, so I figured I'd take a bit of ribbing. Still, I had no way to change, so I planned to go in my suit. It's charcoal grey, in a traditional cut. I wore it with my black Ariat boots, my black Stetson hat, and a bolo tie.
The Cosmos Club turns out not to be a bar at all. It turns out to be...the place where the National Geographic Society was founded in the 19th century. It is contained in a mansion with Second Empire architecture. The interior is as rich as the exterior, and includes numerous treasures of great value, brought back from the corners of the earth and donated by the members.
Well, I'm a gambler from way back, so I simply put on my best poker face and walked right in. The doorman bowed as I entered, and I went upstairs to the gathering.
After a few minutes, a gentleman came up to me and shook my hand. He introduced himself as LtCol Couvillon, United States Marines, and former military governor of Wasit province.
"I had to shake the hand of any man," he said, "who could get in here wearing cowboy boots and a bolo tie."
It worked really well, in other words. You could look ridiculous if you overdo the cowboy thing: if I'd shown up in Wrangler jeans tucked into fancy-stitched cowboy boots, with a pearl-snap shirt and a big sombrero, I probably wouldn't have gotten in. But by blending the styles and pushing the alternate pole as far as you can get away with without looking like you're wearing a costume, you have a striking style that carries you.
You can also swap both poles out for other ones. I was thinking about this over the weekend because of the rather piratical style I adopted for the barbecue, which was coupled (excepting the VFD-issued t-shirt) with my more usual biker boots and jeans. You can look ridiculous if you look like you're wearing a biker costume or a
pirate costume. John Travolta did the one in
Wild Hogs (2007):
If everything you are wearing was bought at a motorcycle shop, you will probably look like a poser wearing a costume. Yet if you swap out the black pants for jeans, the 'biker' wrap for a silk scarf, and so forth, suddenly your aren't wearing a biker costume or a pirate costume. You have a style of your own.
This is similar to Aristotle's approach in his Nicomachean Ethics to finding virtue as the right mean between two extremes. It's not the perfect middle; it will differ for different persons in different situations. Some should go more one way, some more the other. Yet by finding the balance point between two different poles, the one that is right and appropriate for yourself, you come to the best place in matters of fashion as in matters of ethics.
Nor should this be surprising; as I have always said in this space, aesthetics is a division of ethics. The confluence should be expected.