Hello everyone, and welcome to The Rakish Man. My name is Léon Philippe and I am here with all the right responses to your sartorial queries. I’ve poured my first glass of Grand Marnier, so let’s get started.

Dear Lèon,

I was good looking. Many decades and tree rings ago, heads turned. I once heard a waitress say, “YUM YUM.”

Now, my waist size cannot be denied nor sucked in more than an inch for longer than thirty seconds.  My shadow grows akin to the moons of Jupiter. My fashion dilemma approaches the scale of eco disaster.

Should I try to wear my old thirty six inch waist-size pants, if hidden under long coats? Or should I just go to the WalMart section no longer marked “Chunky” but “F...A...T” and just buy actual-size pants that let me breathe but that shame me with their nosebleed-inducingly high waistband numbers?     

Is there mercy anywhere for a my-sized man and will I ever get laid again? Tell me straight. I can take it.

-“Sizeable in Seattle”

Dear Sizeable,

Thank you for your query. First of all, never open with “I was good looking.” It’s about as effective as “I was rich” or “I was married.” Yesterday’s assets are today’s liabilities.

But moving on to your weighty quandary, allow me to quote Oscar Wilde, whose waist size was recorded by a New York tailor, when Wilde was not yet even 30 years old, at 38 1/2 inches.  “To win back my youth,” he said, “there is nothing I wouldn’t do - except take exercise, get up early, or be a useful member of the community.”

It has been ever thus with aesthetes who rank their admiration for the world’s pleasures - youth among them - above their powers of will. The success of these men lies in their acceptance - nay, celebration - of these priorities.

Writer A.J. Liebling was one such figure. He probably never saw a foie gras he didn’t order three of, and yet had far more success with ladies than a married man should.

Many of the male style icons of yesteryear drew power rather than penitence from their pregnant bellies. Winston Churchill hopped his way through every tailor on Savile Row, leaving an unpaid bill at every stop. About half of all the great jazz musicians of the first half of the 20th century - a very natty bunch - were nicknamed “Fats”. Alfred D’Orsay, the great 19th century dandy, went from an Adonis in his youth to a donut in his later years without losing his stylistic preeminence.

These men had advantages that, while rarer today, remain available to you. Firstly, custom-made clothing. You are correct to observe that many of today’s finer clothing manufacturers do not cater to the larger man. Ready-to-wear clothing therefore puts you between a bulge and a soft place - stylish clothing that doesn’t fit or frumpy clothing that does. Neither will do you justice.

A custom-made suit allows you to scale everything to your own dimensions. Not just pants that you can enter into comfortably (and without the distraction of a distributing size tag - and most tailors are discreet enough to avoid scenes such as the one at the 4:00 mark of this clip), but wider lapels, trouser hems, and sleeves, to create a balanced picture. If your means are not quite so ample as the rest of you, you'll just have to look harder for non-skinny off-the-peg suits. Thrift stores can also provide some unexpected treasures. 

Secondly, suspenders, which men of earlier eras used to comfortably and reliably hold trousers at the natural waist. A belt stands no chance against a paunch. It will inevitably end up sliding to the hips, pushing the belly up and out into prominence like a pinched balloon.

Though suspenders are out of fashion today, but this should not concern you. Fashion’s victims are those that follow blindly without consideration for their own circumstances. Self-awareness is the only antidote.

George IV provides an instructive counterexample from the very dawn of modern menswear. He was a large man, and quite the clothes horse - London was scandalized by the expanse and expense of his wardrobe when it was auctioned off at his death. Yet he reached adulthood at a time when male fashion was shifting to clothes that emphasized an athletic frame. This new look flattered the new style’s ambassador, George’s friend Beau Brummell. But it did not flatter George, leading to caricatures like the one above. Their friendship finally ended when Brummell, seeing George and Lord Alvanley at a ball, asked, “Avanley, who’s your fat friend?”

Of course, George had the last laugh. Brummell died of syphilis in France, exiled, alone, and penniless. A limitless bank account and the royal crown still count for something, after all.

Starve your shame, Sizeable, and have done with the wardrobe of your youth. Surely there will be plenty of callers trying to get into your pants, as long as you leave some room to spare.

Ed. note: If you have a query for The Rakish Man, please send an email to david at nomanwalksalone  dot com and I will make sure he sees it.