See out the end of summer – and beyond – in style.

It’s that time of year again where the rules of propriety around when one can wear white are endlessly debated, often ending with some variation on the old adage that “rules are made to be broken”.

First of all, this just isn’t true. Rules aren’t made to be broken, they’re made to be followed. (Just ask anyone in the employment of the Transportation Security Administration.) Second of all, the well-worn rule — thou shalt not wear white after Labor Day — is so woefully out of date that it hardly merits consideration. Most experts say the concept originated in the early 20th century, when New York City’s swells would abandon their workaday dark suits for carefree whites while vacationing in the Hamptons, then revert to more somber-coloured work attire upon their return. Sensible enough, as wearing one’s vacation clothes while at the office remains a faux pas. You’d hardly wear a shirt emblazoned with “I went to Portofino and all I got was this lousy T-shirt” to your office. (Come to think of it, that might be smiled upon in some quarters, but we digress.)

Thirdly, and most importantly, basing your sartorial choices on so-called rules puts you in an impossible position: to follow said rules is to demonstrate a lack of imagination, but to flout the rules is to demonstrate a lack of manners. Neither option is appealing.

So we humbly suggest ignoring the rules altogether, at least in this case. (At the airport, we still recommend taking off your belt, your shoes, and nearly anything else your agent requests.) Instead, we advise dressing for, in no particular order: the weather, the situation, your taste, and your state of mind.

And should you find yourself somewhere warm, or just in an August state of mind, consider wearing the following things.

For years, I have made a point of sporting white denim on the Tuesday after Labor Day as a subtle way of saying “I dress for myself, thank you very much.” Should you wish to join me in this mild act of subversion, Frame + Ben Gorham’s Rodeo distressed denim jeans — a collaboration between some of today’s finest denim makers and the man behind Byredo  — are a fine choice. The off-white patchwork is on-trend, and the straight fit will flatter your legs whether you spent the summer swimming laps in the pool or drinking Aperol Spritz next to it.

Like a horror movie villain, summer weather occasionally lingers long after you thought it had disappeared for good. For that September wedding when the temperature unexpectedly rises north of 30°C, or for a presentation at the office when the commute is barely on the right side of unbearable, this cotton-blend linen suit from Mr Oliver Spencer is your play. It’s light and unstructured (to keep you cool), with a soft, casual texture that will work well into autumn (for a different, but still welcome, kind of cool).

Unless you are Mr Gregory Peck, or have passed the bar exam in Alabama, going full Southern lawyer is rarely a wise move. These swim shorts from Orlebar Brown offer a more elegant way to incorporate the quintessential warm-weather fabric into your wardrobe, a stylish touch for when the fall weather permits a dip (or should you find yourself somewhere enclosed and en-pooled). They also double as a convenient reminder, if not an outright excuse, to book a vacation somewhere tropical during the frigid months.

Leaving your white shoes in the box and saving them for special summer occasions is akin to being the sort of man-child who collects action figures only to entomb them in their original packaging. A wise investment move, perhaps, but hardly any fun. Instead, embrace the same devil-may-care attitude you’re showing by wearing white after Labor Day and beat the ever-loving tar out of these. (These Italian made Connolly driving shoes can handle it.) Consider the ensuing scuffs on your toes as you would the lines on your face: the marks of a life well lived, of obstacles surmounted, of challenges accepted and overcome. Or, you know, the unavoidable, yet stylish, consequence of wearing white shoes in any season.

While we certainly wouldn’t advise wearing such a chapeau for, say, Harvard vs Yale, or a leaf-peeping drive through Connecticut, there are several occasions where this hand-woven hat from Borsalino will make the perfect topper. Such as when the day is hot and you’re working in one last warm-weather picnic in Central Park. Or when you’re enjoying a drink outdoors, wearing a dark suit, perhaps, and humidity peppers the early-autumn air. Or, in the spirit of such Panama hat enthusiasts as Mr Mick Jagger and Mr David Bowie, whenever you damn well please.