Last year, I met a Swiss dude with a taste for luxury. He smoked expensive European cigarettes. Drank the finest spirits. Attended opera by himself on evenings when he was enthralled by the program but could find no suitable companion.

It goes without saying that my pal’s clothes were impeccably tailored. But I noticed that—in between the leather tops of his shoes and the crisp hems of his trousers—he wore bright red socks. Every day, without variation. Which fascinated me. So I inquired. “The red is sensational, isn’t it?” he marveled, gazing down at his own ankles. “So bright, and yet not a hint of orange.”

After much wheedling, I discovered that his signature socks were made by a tiny shop located behind the Pantheon in Rome—best known for supplying tailored clothing to the Pope. I quickly figure out a way to buy these red socks online, and have since tweaked my pal by showing up at his birthday party in matching scarlet hosiery. But my Swiss friend’s attention to his stockings left me with a question: What is the world’s most exquisite dress sock?

Many of us can name the various brands of suits worn by the world’s best-kitted gentlemen. But what about the socks hidden beneath those suits? Surely a market for luxurious male hosiery exists. Yet the fanciest thing I’d ever put on my feet was a pair of freshly laundered, $9 Gold Toes. I wondered just how expensive socks get at the top end of the range, whether they’re worth the price, and, more philosophically, what sort of man is so style-conscious, so rich, and so bonkers that he’d drop significant disposable income on socks.

I called up Alexander Kabbaz, proprietor of the haberdashery website CustomShirt1.com, and perhaps North America’s foremost authority on outrageously expensive socks. You can click here for his dissertation-length essay on sock construction, material, moisture absorption, and “tactile enjoyment,” but for those short on time I will offer a condensed version of his collected sock wisdom:

Your most important consideration is material. There are some beautiful, and indulgent, cotton socks that I’ll be mentioning. But it’s good to remember that cotton doesn’t wick away moisture, which means that feet can get soggy and dank. Over time, cotton socks may get shiny, and their trodden-on heels can become crusty and matted. For the sweaty-footed among us, wool is probably the better choice as it hurries wetness away from the skin. Within the world of wool socks, you’ll find different varietals—merino and cashmere, for instance—and some socks mix in a splash of nylon for stretchability.

You’ll also want to think about how high your socks climb up your legs. Ankle-length will simply not do with a suit. Over-the-calf is standard and, to my mind, the ideal choice. Mid-calf may be comfortable but is a bit of a Johnny-come-lately in the sock world: Before nylon’s stretchy superpowers hit the scene, socks could be suspended mid-calf only with the aid of a pair of garters (which have, for understandable reasons, fallen out of favor with the modern male).

Tailored fit is a given with the expensive socks I’ll be talking about here. These are not formless tube socks. They are shaped to hug the curves of your tootsies, and are offered in incremental sizes. Many have hand-linked toes.

Finally, there is appearance. And here’s the interesting part. While an onlooker might be able to judge the quality of your suit from its cut and material, he will be hard-pressed to do the same with your socks. For one, socks are only briefly and narrowly glimpsed from afar when the wearer is standing upright, and revealed more fully only when the wearer sits and crosses an ankle over a knee. Even given time to stare and assess, a spectator will be challenged to draw conclusions from a few inches of fabric hugging a shinbone. And he will be unlikely to reach out and caress the material, as he might with a jacket lapel.

All of which means that appearance is a surprisingly poor way to advertise the princely sum you’ve spent on your socks. You’re much better off with a compelling back story. This is what my Swiss friend understood. And so, I present to you several socks that, when worn and then carefully dropped into conversation (preferably while tugging up a trouser cuff to display them), will 1) lend you an air of sartorial splendor, 2) imbue you with a soupcon of worldly expertise, and, less charmingly, 3) make you seem like an obnoxious fetishist who spends his money on all the wrong things.

From least expensive to most:

Gammarelli

These are my Swiss buddy’s signature socks. They hail from a shop in Rome that has clothed popes, bishops, and cardinals for two centuries. They boast an unparalleled back story for the money (a relatively affordable $27 per pair). And indeed, the reds and purples of these socks are eye-meltingly vivid. The pair that was shipped to me was disappointingly made of cotton lisle material—with my sweaty dogs, I tend to be a wool guy. And the fit was actually a bit gappy around my heel. Still, I’ll be wearing these whenever I’m in the mood for a splash of blinding color and papal pomp.

Comfort: Excellent. Though I’d prefer them in wool.

Appearance: Distinctive. This sock is so bright your wingtips will have to wear shades.

Foppish back story: Delightful. Wear the socks that grace the Pope’s divine feet!

Pantherella merino

Another sock brand steeped in history. For decades, British-made Pantherellas were considered the gold standard in men’s hosiery. Kabbaz feels the brand has lately slumped; on his site, a prominent banner touts “Old Pantherella.” But I was a fan of the 70 percent merino, 30 percent nylon pair I tried. They extended well above my calf but were perfectly contoured to duck into the hollow at the back of my knee. Easy to pull on in a single motion, and never constricting. My sole problem with these $27 socks was their translucence. The gray pair I tried revealed hints of ghostly flesh beneath the thinner ruts of its ribbing. If there’s one attribute I demand of my socks, it’s total opacity.

Comfort: Superb. You’ll barely realize you’re wearing socks at all.

Appearance: More translucence than I’d like.

Foppish back story: Romantic! A proud hosiery house lately fallen out of favor.

Falke “Airport” socks

Falke is a classic brand, around since 1895. But these socks left me cold. At 60 percent wool, 23 percent cotton, 15 percent nylon, and 2 percent elastic, they were a melting pot of fabric. They bunched up at the tops of my feet, and it was easy to tell they were not shaped as expertly as the other brands I tried. Also, the knee-high model ($32) was much too long for my taste, easily extending up onto my thighs. That’s way more sock than I ever want to deal with.

Comfort: So-so.

Appearance: Blah.

Foppish back story: Anything with the word “airport” in it will not be favored by this metric.

Bresciani 100 percent silk

Talk about translucence! You can see right through these $59 socks. Which is disturbing and gross: I did not enjoy viewing my clotted leg hair through the fabric. It made me look like I was wearing pantyhose. The socks’ one design element, a faint racing stripe up the sides of the calves, didn’t help any.

Comfort: Silky.

Appearance: Eww, bunched leg hair!

Foppish back story: We are now getting into materials and retail prices that should satisfy even the most foppish among us.

Bresciani 100 percent sea-island cotton

Another $59 entrant from the Italian hosiery specialists. Sea-island cotton is a sumptuous fabric—a delight to rub across the cheek. (Before you’ve worn the socks, not after.) But it won’t wick as efficiently as wool. And for all its charms, sea-island cotton is still not nearly as warm or soft as cashmere. Be patient, for there is cashmere on the horizon …

Comfort: Blissful. Though again, it is my feeling that wool has more utility.

Appearance: These socks do look pleasingly creamy.

Foppish back story: Most men cannot afford to buy shirts made of sea-island cotton. Stoke their envy by revealing that even your socks boast mind-blowing thread counts.

Zimmerli 100 percent Cashmere Dress Weight Over-the-Calf

To most observers, these will look like ordinary black socks. They are far from ordinary, mostly by dint of the fact that they cost $200 a pair. Even better: Kabbaz says you can wash them only six or seven times before they begin to disintegrate. Does it make any sense at all to buy 100 percent cashmere socks? Of course not. And yet: When I pulled them on, it was as though I’d dipped my feet into baths of warm butter. I have never worn anything more comfortable—on any part of my body. What do you get for the man who has everything? $200 socks that can be worn six times. We have a winner: The world’s most exquisite (and most ridiculous) dress sock.

Comfort: Unmatched. Like walking on clouds of ghee.

Appearance: Surprisingly humdrum.

Foppish back story: These socks are in some ways the most outlandish fashion item a man could ever buy. Disclosing what they’re made from and what you paid for them will likely win you a mix of admiration, disdain, puzzlement, and punches to the face.

Note: Sock samples were provided at no charge by CustomShirt1.com, Mes Chausettes Rouges, and Pantherella.