In the previous installment of The Streetorialist I made reference to occasionally pairing hightops with a suit, and took a bit of a shellacking in the comments section.

More on that later, but suffice to say that it got me thinking, particularly about ‘rules’ in men’s fashion, and my inextricable conviction that the very concept of rules governing one’s personal style is bullshit. It’s not racquetball. It’s about ones innate instinct to express themselves aesthetically.

No two people are likely to patently agree on something as intrinsically personal as style. In the late 90s I rolled my eyes at those suburban ravers channelling Marcel Marceau with plastic pacifiers and 40″ trou cuffs just like everyone else I knew, but make no mistake, those kids were getting laid. So someone must have thought it looked good (an aesthetic determination on drugs is still an aesthetic determination).

As X said, this is a game that moves as you play. The rules keep shifting, but rarely do they get there on their own. Stubbornly determined aesthetes throw caution to the wind, and sometimes pull it off so elegantly that the rest of our sartorial convictions come running to jump on the wagon as it rolls away.

Read the rest of the article after the jump.

At the beginning of the 20th Century a man’s standard outfit was a grey flannel suit, oxford shirt, unadorned tie. Nothing wrong with that, holds up to this day. It simply lacks personality. Then along came the Supreme Commander of the boulevardier, the Duke of Windsor, without whom the Repp tie would remain strictly military, two-toned shoes would be shunned, tweeds and flannels would be textile non grata in the city, and no one would dare wear a sweater or polo under a blazer.

Not all attempts at flouting convention catch on. Few followed Oscar Wilde’s example in dressing in a coat shaped like a cello at the opening of the Grosvenor Gallery (at least until Hussein Chalayan showed up many decades later).

Good looks catch on, and gradually become part of our colloquial shared aesthetic, which is ever shifting. Catch an episode of Mad Men; the blokes in the art department are wearing pinstriped suits. Now it would be Chucks, and a gingham or flannel under a herringbone. Both looks can kill, equally.

All of us, as streetwear afficionados, openly toy with, flaunt, discount, or outright curb-stomp these supposed rules on the regular. And it has had a huge, lasting (and multi-billion dollar) impact on the men’s fashion landscape, and will continue to.

Looks will pop up, blow up, die, and be reborn. Every now and again we’ll see something like Pee Wee Herman’s costume wind up reincarnating as a Thom fucking Browne collection. But then, that’s why we all love this merry-go-round that is fashion. It ebbs and flows, bleeds and builds, always per our personal experiences.

And so, to get back to what started me on this little monologue, those assertions that trainers paired with a suit are an absolute no-go. It’s a tough look to pull off, to be sure. Requires quite a few things. Not just the right shoes and the right suit, but also the right event, attitude, context.

It’s not something I often attempt, and I’m sure I’ve failed with it more than once. However, it’s still a look that can work, if everything comes together. And I say this as something of an anachronist, the kind of person who still insists on dressing up for flights, as a silent protest against trans-continental sweatpants.

A couple years ago I went to a big opening hosted by Louis Vuitton, shortly after someone there had been good enough to hook me up with a pair of those pink & grey Kanye x LV hightops. The event clearly called for a suit, but there’s no way those shoes were staying in the box. Was I wrong?

I’ll probably think about it twice as hard the next time I’m about to wear Dunks to a sitdown dinner. But, then again, trainers and suits are worn together by the two most stylish men I know of, Lapo Elkann and Waris Ahluwalia, so what do I know?


Text by @quentincrispy

Read Streetorialist Lesson 1 here.

Read Streetorialist Lesson 2 here.

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