In his 1966 essay “The Secret Vice,” originally published in The New York Herald Tribune, the white-clad chronicler of American culture, Tom Wolfe, starts by talking about men who love handmade buttonholes. This was, of course, before surgeon cuffs were standard on ready-to-wear, but the passage will ring true to anyone who’s ever obsessed over the details. 

“Real buttonholes. That’s it!” Wolfe exclaimed. “A man can take his thumb and forefinger and unbutton his sleeve at the wrist because this kind of suit has real buttonholes there. […] Yes! The lid was off, and poor old Ross was already hooked on the secret vice of the Big men in New York: custom tailoring and the mania for the marginal differences that go into it. Practically all the most powerful men in New York, especially on Wall Street, the people in investment houses, banks and law firms, the politicians, especially Brooklyn Democrats, for some reason, outstanding dandies, those fellows, the blue-chip culturati, the major museum directors and publishers, the kind who sit in offices with antique textile shades – practically all of these men are fanatical about the marginal differences that go into custom tailoring.”

The phrase “it’s all about the details” has been exhausted, but in classic men’s tailoring, it’s still true. Suits and sport coats follow a template that’s the result of many generations and skilled hands. But there’s still plenty of room for personal expression. Much has been written about pocket styles (jetted, welted, and patched), lapel shape (peak, notch, straight, and bellied), and closure (single button, two-button, three-roll-two, and the never to be worn hard-three). However, there’s not much online about how the edge of a coat can be finished. It’s a detail that’s easy to forget but can make a surprisingly strong impact on how a garment looks. Here’s a run-through:

Log onto Instagram, StyleForum, and Reddit’s Male Fashion Advice on any given day and you’ll find hundreds, if not thousands, of fit pics. Fit pics, short for outfit pictures, is the online term for posting a photo of yourself to show your outfit of the day. On Instagram, there are thousands of such accounts, along with What Are You Wearing Today (WAYWT) threads on dozens of specialized online forums. Fit pics are posted in every type of men’s style community imaginable — classic, streetwear, and the avant-garde — but nearly all of them share one thing: they are headless.

Whether cropped, blurred, or blacked out, most of these photos are altered to hide the person’s face. Why? Women are fine with showing their faces through fit pics — which are called mirror pics in womenswear — although they’ll occasionally make a silly expression to take the edge off an inherently ridiculous act. It’s rare, however, for men to reveal their identities. When pressed, most will tell you they simply value their anonymity. While that’s undoubtedly true for some, I think the real reason goes deeper.

Three men shaped modern men’s fashion. The first was Beau Brummell, who gave us the suit. The second is Edward VIII, who gave us style. The third is Oscar Wilde, who gave us our stereotypes. Together, they form much of modern menswear culture, even for those who never wear a coat and tie.

Pitti Uomo is the twice-a-year menswear tradeshow in Florence, Italy, where industry buyers and sellers meet so they can coordinate their seasonal offerings. But at last month’s Pitti Uomo, there was a strange and unexpected booth. It was nearly all white, had angular shelves, and showcased a new line of ready-to-wear shoes. Above the display, a printed banner read, “Foster & Son.”

For the last hundred years, London’s bespoke tailoring and shoemaking trades have prided themselves on being different from ready-to-wear. Many companies took great pains to explain how custom-clothing is superior to factory production. Additionally, the Savile Row Bespoke Association tried, albeit unsuccessfully, to guard who can use the term bespoke. But in the last ten years, there’s been a shift. Many of London’s best bespoke firms are now using the craft side of their business to give their ready-to-wear lines a halo — something Parisian haute couture houses have been doing for decades.

The venerable firm Foster & Sons has carried the grand tradition of bespoke shoemaking since 1840. They’re part of a small group of custom shoemakers located on the West End, sitting alongside names such as John Lobb and George Cleverley. During England’s medieval period, London was split into two halves. There was the proper city of London on the east, which was a center for finance, banking, and law. Then the City of Westminster on the west. When King Henry VIII built his new royal palace on St. James in the 16th century, he brought with him his aristocratic following. Wealthy elites were happy to live west of London because the pleasurable countryside was usually upwind of the smoke drifting from the crowded City. Over time, as money poured into the area, the West End became known for all the things associated with British aristocratic life — shopping, leisure, gentlemen’s clubs, government, and bespoke shoemaking.

In March of 1973, when men wore long hair and women sported bell-bottom jeans, The New York Times published an article by pioneering feminist scholar Carolyn Heilbrun. The article, titled “Androgynous World,” is about the persistence of the androgynous ideal. The United States at this time was at a flashpoint. While gender stereotypes were becoming more rigid, fashionistas and feminists were imagining a freer future. About five years earlier, Pierre Cardin and Paco Rabanne conjured up streamlined “Space Age” jumpsuits made from stretchy, synthetic fabrics as a way to imagine a unisex world. Second-wave feminists were also pushing back against the gender stereotypes of the previous decade. Many feminists believed girls were being lured into their subservient roles by first accepting gendered clothing expectations. To be equal to men, they’d dress like them – or, at least, in ways that weren’t traditionally feminine.

“The idea of androgyny apparently takes a little getting used to. First responses tend either toward bewilderment or hostility. The word itself is easily enough defined for the bewildered: comprising the Greek words anthro (male) and gyne (female), it suggests the unity rather than the necessary separation of what we have come to think of as masculine and feminine qualities,” Heilbrun wrote in her article. 

“For the hostile, who in some sense feel threatened by this unfamiliar idea, further assurance is required. Androgyny does not mean the loss of all distinctions; those who are terrified by the word probably envision everyone, man and woman, dressed indistinguishably, like members of the Chinese Army. Those who are terrified further assume that in robbing us of clearly delineated sexual models, androgyny will rob us of all order and sanity. If we are to have more than two accepted role models — in youth, the quarterback and the cheerleader, in later life, the corporation manager and the corporation manager’s wife — will we not, in fact, be diving off the edge of an ordered world into the abyss?”

The Talented Mr. Ripley, the film version and not the book, opens with a brilliantly economical line about clothes. Matt Damon, as the film’s anti-hero Tom Ripley, borrows a Princeton jacket from a friend while working as as a piano player at a party. The Ivy League jacket ends up getting him the attention of a wealthy shipbuilder, who thinks that Tom went to Princeton with his son Dickie. He sends Tom away to Europe, hoping Tom can convince his ne'er-do-well son to come back home from southern Italy. Having left his bleak Manhattan life, however, Tom becomes enraptured by Dickie’s charming dilettante lifestyle. So he strikes up a Faustian bargain and steals it. “If I could just go back … if I could rub everything out … starting with myself, starting with borrowing a jacket,” Tom silently dreams to himself at the beginning of the film. And doesn’t Tom’s line neatly sum up what we all wish for when we purchase a new jacket or pair of shoes? The fantasy that it’ll somehow magically transform our mundane lives? (Well, maybe without the murderous crime.)

The film is important to fashion in other ways. Every summer, men reference Anthony Minghella’s chilling thriller as one of their favorite sources for warm weather style inspiration. The Talented Mr. Ripley captures the feeling of being young and carefree, not unlike the films of French New Wave, but with more of a la dolce vita vibe and touristy idyllic scenes of a sun-drenched 1950s Italy. It’s a hypnotic, voluptuously beautiful film with tons of references to menswear cliches: inherited wealth, Ivy League education, and an impossibly glamourous lifestyle in an Italian seaside town. 

For that Dickie Greenleaf vibe, even if not its literal look, you can turn to Joyce. The relatively new brand offers the same laid-back, vacation style that defines the film. Their clothes are loosely cut, retro-inspired, and pair well with tortoiseshell sunglasses and well-mixed martinis. The company even has the same America-to-Italy backstory. The idea for the brand was first seeded when John Walters, the company’s founder, was working as a product designer in New York. However, it didn’t materialize until Walters visited his girlfriend in Florence, Italy (where they now both live). Today, it’s based out of their Florentine studio, while product fulfillment takes place out of Indian Wells, California. “Stylistically, our online visuals reference a lot of Pink Floyd’s earlier works, as well as some of Alain Delon’s films, such as Purple Noon and The Swimming Pool,” says Walters. “Aside from that, we also get a lot of our style inspiration from traveling.”

In her 1941 short story “The Standard of Living,” Dorothy Parker explores the all-too-familiar themes of escapism, materialism, and innocence. Two young “18-dollars-a-week” stenographers, Annabel and Midge, saunter down Fifth Avenue one Saturday afternoon while playing the game, “what would you do if you had a million dollars?” Through a chaste and elegant shop window, they spy a double rope, pearl necklace at one of Manhattan’s most exclusive jewelry stores. Yes, the first thing they’d do is buy this exquisite necklace, but how much do they imagine it costs? The girls assign a probable value of $1,000 — $10,000 at the most, they reason — before they summon the courage to go inside and inquire. But when the white-gloved salesman tells them it’s a quarter of a million, they stumble back onto the street. “He’s got his nerve!” Annabel exclaims.

The story goes on with Annabel and Midge dreaming of getting more money, supposing what they could purchase if the owner of that pearl necklace bequeathed them ten million dollars. What even more valuable thing they could buy that’s not so common? Of course, nothing is enough. They never imagined a stringed-up bauble could cost so much money, but upon learning its value, they start to wonder what’s around the corner.

“The Standard of Living” will sound uncomfortably familiar to anyone building a better wardrobe. The first pair of Allen Edmonds seems staggering until, at some point, you find yourself purchasing Crockett & Jones and looking around the corner at Edward Green. But plenty of things on the lower end of the price spectrum are, in fact, quite good. Parker’s story is about the elusiveness of contentment and escapism of glamour.

While fashion writers focus on the runway, actual fashion moments often happen on film. Marlon Brando’s smoldering look in The Wild One helped to cement the black double rider as the rebel uniform, just as the opening scene of Breakfast at Tiffany’s refashioned the black, sheath evening dress into a womenswear icon. In his 1985 book Elegance, Bruce Boyer calls these cinematic touchstones the “moments that signal or symbolize a shift in the old modus oprandi.” These scenes, as unimportant as they may seem, later become the film equivalents of the most memorable lyric in a song. And in being so, they change the ways we see clothing.

Boyer traces the moment when tassel loafers became an acceptable form of business dress to a particular scene in the 1962 film That Touch of Mink. The scene starts with Cary Grant, who plays the familiar international corporate head, walking into his wood-paneled office on Madison Avenue one average morning. “He’s wearing his familiar dark, impeccably cut business suit, white shirt, conservative tie, and black straight tip oxfords. He is the very glass of business fashion, the mold of form,” Boyer writes. Yet, upon settling in, Grant “removes his suit jacket and town shoes, and dons a discrete, but obviously very comfortable, lightweight cardigan and a pair of tassel loafers! Right there in the office!” In today’s business culture, where everyone wears jeans and sneakers, this story has a quaint ring to it. But as Boyer notes, this is just one of the many “less-than-earthshaking events that mark the road we have traveled.”

A similar moment happened for the sweatshirt, that mass-manufactured item that has none of the rock ‘n roll cool of biker jackets or the blue-collar credibility of blue jeans. Yet, when Steve McQueen wore a dusty blue sweatshirt in the film The Great Escape, particularly in that scene when “The Cooler King” raced through the mountain trails and slid into a barbed-wire barrier, the garment attained a touch of cool. The sweatshirt is as iconic as every other notable American garment – blue jeans, black double riders, sack suits, penny loafers, and button-down collars – and it symbolizes the same independent American spirit. Much of that is thanks to McQueen (or, really, his stunt double, Bud Ekins, who did the hard work in that chase scene).

It’s that time of year when I post a spat of seasonal sales. The third big one started this morning: No Man Walks Alone, where you can find select items discounted by as much as 40% off. Their sale is one of my favorites for two reasons. The first is that I get to post a photo of the shop’s founder, Greg Lellouche, and note that he is, in fact, walking alone. The second is the shop’s selection. While No Man Walks Alone is a sponsor on this site, they’re also one of my favorite online retailers. Along with some excellent tailoring, they also carry Japanese workwear, contemporary casual, and a bit of the avant-garde.

The selection here is big, but not massive. It’s reasonably easy to scroll through the entire sale selection to see if there’s anything you want, but No Man Walks Alone also has filters on their site so you can narrow in on sizes, colors, and brands. Some of my favorite makers here include Sartoria Formosa, Drake’s, and Kaptain Sunshine. If you’re looking for highlights, here are ten things that I think are notable.

Valstar’s Plaid Wool-Alpaca Topcoat