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It’s hard to believe that it took until May 1939, the spring before the start of the Second World War, for Vogue to publish its first cover of a fashionable woman in trousers. We know the image still had the power to shock because the editors assuaged anxious readers by saying that, while pants were considered masculine at the time, they can still be worn in conventionally feminine ways. “If people accuse you of aping men, take no notice,” they wrote encouragingly. “Our new slacks are irreproachably masculine in their tailoring, but women have made them entirely their own by the colors in which they order them, and the accessories they add.” In the photo, the woman was shown wearing a pair of ochre-colored sharkskin trousers with delicate jewelry, Moroccan slippers, and a scarlet jersey shirt with a plunging neckline. A silk scarf was wrapped around her head like a turban, with a turquoise encrusted pin holding everything together.

Since that cover was published, women have adopted nearly every masculine symbol into their wardrobe, from blue jeans to bomber jackets. But examples of men imitating women’s dress are rare. When they do, they’ll counter criticism by citing men’s earlier use of the style. A belted robe coat isn’t something your aunt would wear, but rather a reference to the earliest iteration of a polo coat, as seen on the strong-shouldered Richard Gere. Cuban heeled Chelsea boots aren’t so much high-heeled as they are Beatles-esque. And when long-haired youths were criticized for their appearance in the late 1960s, they pointed to how Jesus is often depicted with shoulder-length locks.

Kenji Kaga, the silver fox behind Tie Your Tie, has no problem telling you that he’s inspired by femininity — and he’ll do so without qualification. When I talked to him last month, I didn’t get the impression that he was saying so for political reasons. Instead, as an aesthete, it didn’t occur to him why he should do otherwise. “Most ties today come in stripes or small geometrics, such as the ones you might find at E. Marinella or Drake’s,” Kaga tells me. “Ours are inspired by vintage designs from the turn of the century until about the 1930s. I’m most inspired by French design, which I like for its femininity. The lines are more fluid and romantic; the design less symmetrical. When we color our collections, I also take inspiration from women’s collections, such as Saint Laurent, Celine, and Valentino. Very old designs, but in new colors. This is our style.”

There’s a small shop in Rome called Gammarelli that’s tucked away behind the Pantheon. At first glance, it may not seem different from the many family-owned clothiers scattered throughout Italy. The small, rectangular space is fitted with glass counters and glossy wooden shelves. On the main floor, there are bolts of cloth stacked neatly on top of each other for customers to peruse. Towards the back of the shop, an old, wooden staircase spirals up to the workroom, where tailors labor away on benched tables peppered with pincushions and pieces of chalk. The shop’s head tailor can sometimes be seen here running up and down between the floors for fittings, while a tall, bearded man in a tweed sport coat on the main floor scribbles down orders on a notepad. But between the worsted wools and crisp cotton wovens, you’ll also see deep purple robes, ceremonial swords, and feather-trimmed hats. On the signage outside the shop, below the name Gammarelli, the words read: Sartoria Per Ecclesiastici, or “clerical outfitters.”

If there’s such a thing as timelessness in dress, you can find it here at Ditta Annibale Gammarelli, purveyors of ecclesiastical clothing since 1798. For over 200 years, whenever a new pope is elected, the shop’s tailors and managers rush out the Vatican to meet the supreme pontiff in a chamber called the Room of Tears. They present to him a custom, white papal cassock, cut to a floor-brushing size, and made with some thirty handsewn buttonholes. The Pope slips into his Gammarelli garb and dons the traditional papal accessories: an ermine-trimmed red velvet shoulder cape known as a mozzetta; a white skullcap known as a zucchetto; and a pair of red leather papal shoes. He then steps out on the balcony of St. Peter’s to greet the faithful. 

Over the years, after this initial ceremony, each Pope has accessorized his dress slightly differently. John Paul II ditched the red slippers in favor of cordovan colored walking shoes made in his native Poland. When Benedict XVI restored the use of swanky bright red slippers for outdoor attire, Esquire voted him “Accessorizer of the Year.” That prompted the Vatican’s official daily paper to issue the stern reply: “The Holy Father is not dressed by Prada, but by Christ.”

Mr. Porter’s massive selection puts them in everyone’s orbit. Whether you favor classic tailored clothing, Japanese workwear, or oversized, minimalist contemporary garb, Mr. Porter likely carries more than a handful of brands for you.

Today, Mr. Porter started their Black Friday promotion, where you can take up to 30% off select items. Inis Meain’s sweaters are expensive, even with the discount, but absolutely exquisite and a joy to wear. Engineered Garments, Blue Blue Japan, and Kapital are personal favorites for workwear; SNS Herning is great textured knitwear you can layer under heavy coats (be sure to size up). 

Given the scope and size of their inventory, your best bet is to filter by sizing and brands to see what you like. That said, here are ten items that I think are worth highlighting. 

I remember when Black Friday was about waking up early to try to beat the crowds, only to wind up standing in line and wondering whether the savings are worth the trouble. Thankfully, nowadays, everything is held online, which means you can snag the best deals without ever having to leave your couch. But still, it helps to have some intel.

Every year at Put This On, I roundup Black Friday sales for our readers. The list, which comes out on Friday, is massive and often reaches into the hundreds of stores. For those who want something more manageable, I also list some of my favorites here. Since some stores have already started their promotions, here are nine early-bird specials that I think are notable. More will come as the week moves on and new deals emerge. 

In the early 1980s, when prep and power dressing dominated the American landscape, a few Japanese designers were preparing for a revolution. In the West, many of our trends in literature, architecture, and fashion derive from the Regency era. We wear navy suits because, in the early 19th century, British men of means paired navy coats with cream-colored breeches. About a generation later, Regency blue gave way to Victorian black when Queen Victoria decided everyone should look somber. Nearly 200 years later, these norms remain. Most men today wear navy, black, grey, and white — following in the steps of those early-19th-century traditions — and pair navy coats with lighter colored trousers because of Beau Brummell.

For a select few, this all changed in 1983 when Rei Kawakubo and Yohji Yamamoto debuted their now-legendary spring/ summer collections in Paris. Thoughtlessly dubbed the “beggar’s look” by critics, these so-called rags were quite calculated in their design. Their asymmetric, deconstructed, and artfully ripped clothes enshrouded their wearers in mystery. As Yves Saint Laurent noted, fashion in the early 1980s was all about color and lots of it. These Japanese artists, on the other hand, deliberately avoided vivid color and made heavy use of a monochromatic palette, from “strong and varied hues of black to the simplicity and crispness of shades of white.”

“Kawakubo’s and Yamotmo’s black was often an unassuming, harmonious shade, reminiscent of Japanese ink painting,” wrote the authors of Future Beauty: 30 Years of Japanese Fashion. “Their expressive use of a black palette also partook of the qualities celebrated in Jun'ichirō Tanizaki’s book In Praise of Shadows (1933), which finds in shadow the essence of the Japanese aesthetic and speaks of the Japanese skill with light and shade. The designers’ choice of color, unfettered by any Western paradigm, was perceptively singled out by The Washington Post as the distinguishing feature of their style, along with the purity of their aesthetic. The French newspaper Libération likened Kawakubo’s and Yamamoto’s creations to their intense black-and-white films of Kenji Mizoguchi, while French Vogue compared them to calligraphy scrolls, which symbolize a beauty devoid of color.“

In his book Gentleman, Bernhard Roetzel opens his chapter on overcoats with an amusing observation about dress coat culture. Superficially, outerwear is designed to keep us warm and protected from the elements. But even in temperate climates, overcoats figure into people’s wardrobes because people feel a need to put things on and take them off. Dress coats are part of the language of making an entrance, a gesture that’s first communicated through old films and TV shows. There’s something romantic about shuffling a coat off your shoulders before you sit down at a bar or restaurant. 

“By putting on his overcoat, a man indicates his intention to leave. By taking it off, he indicates that he has arrived,” Roetzel writes. “Only when he has been relieved of his overcoat does he begin to make his entrance. But the man who arrives without taking off his overcoat is signaling reserve, distrust, or just indecision. ‘Later the whole crowd went to a bar, where at first everybody stood around in the overcoats …’ wrote Max Frisch in Gantenbein (also known as A WIlderness of Mirrors), outlining in a few words a situation that is as yet unresolved.”

Perhaps that’s why I find raglan overcoats so appealing. In my mind, they’re like a modern version of a cape, the most dramatic of entrance clothing. I can imagine myself curling a coat’s edge between my fingers and palm, then swirling the coat behind me before it settles cleanly on my shoulders. Naturally, you’ll need to ask friends and family members to stand back, so the swirling cape — or I mean coat — doesn’t hit them in the face. If there are enemies nearby, however, give them no warning. 

In academia, and particularly social science, research methods have become more rigorous, but the field has produced fewer big thinkers. Take David Ricardo, for instance, the British political economist who transformed the world at age 37 after reading Adam Smith’s Wealth of Nations. Having already made a fortune as a stockbroker and loan broker, Richardo published his first political economy paper on the “bullion controversy” in 1809. He posited that the Bank of England’s propensity to issue excess banknotes was causing inflation, an early theory in what is today known as monetarism. A few years later, in his “Essay on the Influence of a Low Price of Corn on the Profits of Stock,” he articulated the law of diminishing marginal returns.

His most significant contribution, however, came when he studied Britain’s protectionist Corn Laws. Using the simple, yet profound example of how Britain could trade cloth for Portuguese wine, he formulated the idea of comparative advantage — the basis for much of free trade thinking today. Like other great political economy theorists before him, such as Adam Smith and Karl Marx, Ricardo had the uncanny ability to arrive at complex conclusions without the mathematical tools deemed essential in today’s academic research. In his book Price Theory, David Friedman wrote of the man: “The modern economist reading Ricardo’s Principles feels rather as a member of one of the Mount Everest expeditions would feel if, arriving at the top of the mountain, he encountered a hiker clad in T-shirt and tennis shoes.”

Ricardo’s examples, however, were not arbitrary. Portugal at the time was renowned for its sweet port wine, and Britain excelled at producing woolens, linens, cottons, silks, and all things textile related. In the Scottish Border towns, tweeds and cashmere were woven and knitted from local and native wools. Further south, Manchester’s steam-driven textile mills produced almost a third of the world’s cotton, thus giving the city its nickname, Cottonpolis. Spitalfields, similarly, was known for its exquisite and lustrous silk. French Protestant refugees (Huguenots) in the 17th century established the silk trade in this East London district after fleeing from religious persecution. The tradition was later taken up by Irish immigrants who arrived with little more than their weaving skills. It was a simple example involving Britain’s textile industries that helped to set up the following 200+ years of economic theory.

When I lived in Moscow, Russia many years ago, I relied on my gray flannel trousers, tweed sport coat, and waxed cotton jacket to get me through fall. Superficially, the primary function of an autumn wardrobe is to protect you from cold, wind, and rain. But in a faraway, foreign land, cocooning myself in layers also brought some psychological comfort. The renowned Russian playwright Anton Chekhov – whose haunting and lyrical prose helped define the modern form of short storytelling – wrote about this feeling over 120 years ago in his story, “The Man in the Case.”

[T]wo months ago a man called Byelikov, a colleague of mine, died in our town. You have heard of him, no doubt. He was remarkable for always wearing galoshes and a warm wadded coat, and carrying an umbrella even in the very finest weather. And his umbrella was in a case, and his watch was in a case made of grey chamois leather, and when he took out his penknife to sharpen his pencil, his penknife, too, was in a little case; and his face seemed to be in a case too, because he always hid it in his turned-up collar. He wore dark spectacles and flannel vests, stuffed up his ears with cotton-wool, and when he got into a cab always told the driver to put up the hood. In short, the man displayed a constant and insurmountable impulse to wrap himself in a covering, to make himself, so to speak, a case which would isolate him and protect him from external influences.

There’s something oddly comforting about fall/ winter clothes, not just in terms of how they keep you warm, but also emotionally protected. Encased in woolens, with a Scottish cashmere scarf around your neck and your coat’s collar turned-up, you feel like you can take on the world. At the same time, there’s something genial about autumnal clothing — materials such as soft cashmere, nubby oxford, and suede leather invite a smile and conversation. The other day, a stranger complimented me on my outfit. It felt warm.