Shaniqwa Jarvis

Men — a lot of men, most men — don't always know their suit doesn't fit correctly until they try on a well-tailored suit that does. It doesn't always occur to most men that the sleeves of their button-down shirt are billowy until someone hands them a shirt with the sleeves cut slimmer, so you can actually make out the arms inside. They could go half their career wearing blazers with straight sides — the line from the armpit to the hip — until someone pinches in the fabric at the back, revealing that blazers look better when made with perhaps 7 percent less material, for snugness around the middle. Only when he sees these garments, feels them wrap and hug the contours of his body and his alone, will a man be convinced, because men require proof. So you can tell a man that, for example, his blazers are too boxy, and he might not even doubt you, but he won't do anything about it, and he won't understand that he might feel better, walk taller, in a blazer that really fits him until you pinch that fabric at the back. Until you show him. It's like the difference between explaining the benefits of countersinking a screw into a piece of wood and grabbing a drill to demonstrate it.

Oh. That's what you mean.

And once he is convinced, he is convinced for life.

Five years ago, J. Crew, a clothing company that at the time was not known as a brand for men, that at the time was not known for much of anything in particular besides its catalogs full of toothy models wearing preppy clothing available in cleverly named colors like "bright flame," decided to try something new in the $400 billion world of men's clothing. It would design and produce a few essential pieces that every man should own — the best suit, the best shirt, the best pants, the best jeans — which would look cleaner and feel better than what men had come to expect from most stores and brands. The cuts would be slimmer. The notches on the lapels would be tighter, and the lapels themselves would be narrower. The spread of the shirt collar — the distance between its two points — would be exactly right, whatever that meant. (They would know it when they saw it.)

So that was the first thing: Make clothes that fit.

And then, once they did that, they would surround their own creations with a handful of shoes, shirts, watches, and other accessories made by iconic companies. Why try to reinvent the men's dress shoe if Alden already makes some of the best on earth? Why not enlist one of the world's great shirtmakers, Thomas Mason, to help design the world's greatest shirt? J. Crew, an independent company whose clothes were not available in any department store, would itself create a sort of miniature department store for men only.

That was the second thing: Show men how to wear clothes. Give them options. Make suggestions. Encourage.

And that was J. Crew's plan, five or so years ago, and it was a good plan except for the huge risk. The huge risk was that men wouldn't notice. That they would keep wearing slightly ill-fitting clothes that weren't quite ill-fitting enough that men would feel impelled to make a change. That men just don't really care.

Shaniqwa Jarvis

A man's voice rattles over the intercom at J. Crew's headquarters in downtown New York.

"Jenna Lyons, call me, and...who else would know? When the light went off? Went on, I'm sorry. Libby? Or Charlie. Charlie. All three of you, call me."

This is the voice, straight from the Bronx, of Mickey Drexler, J. Crew's CEO since 2003. He does this all day long — talks into the intercom, interrupting his thousand employees with rambling thoughts, requests, compliments, field reports from J. Crew retail stores. Just now he's asking three of his top lieutenants to call him: Lyons, the president and executive creative director; Charlie Phillips, the head merchant for the men's division; and Libby Wadle, the company's executive vice-president and head of merchandising.

Drexler was already a legend when he took the job — he spent nineteen years at the Gap, becoming president of the company in 1987 and CEO in 1995. He turned it from a cheapo mall store into a smart mass-market brand that romanticized khakis through ads featuring Jack Kerouac and Sammy Davis Jr. During his tenure the company's sales rose from $400 million to $14 billion a year. It spun off Baby Gap and Gap Kids, and Drexler launched a new store, Old Navy, which now has a thousand locations. When he arrived at J. Crew, it was a perfectly decent catalog retailer with a nice following. But he did not have any particular expertise in men's wear, and the 1990s and early 2000s had not been an inspired time for men's style at J. Crew or many other companies. (Just watch pretty much any episode of Seinfeld for a reminder of how bad things were.) At J. Crew, at the Gap, at most stores, men's sections were relegated to the back of the store and to the end of the catalog.

Jenna Lyons glides into Drexler's office after her summons on the intercom. He asks her: "When did the light go off that we were gonna go after men's in a different way? I remember saying, 'Clothes suck out there. Where do guys shop?' I remember saying, 'No one's doing something right.' I vaguely remember saying that."

Lyons, who is well over six feet tall and speaks with both the warmth and understated authority of someone helping you with your homework, answers immediately: "I remember, very specifically, a meeting where we went from the women's presentation to the men's presentation" — four times a year, Drexler and select staff are shown the clothing that has been designed for the coming season, for both men and women — "and you said, 'Why is it that the women aren't dating the men? Why don't these two things have anything to do with each other?' And you just kind of exploded with excitement about what it could be."

The reason for the sorry state, at J. Crew and elsewhere, was probably the lingering effects of the Casual Friday movement, which not only encouraged men to wear baggy cotton pants and blue button-down shirts to the office but codified the notion that a man needn't worry about distinguishing himself or doing anything other than clearing the lowest possible bar. Lyons compares the period to Rumspringa, when sheltered Amish teenagers are free to go out into the world and experiment with drugs and sex and other horrible things. Most return to the church, chastened by their little dance with the devil. "I think Casual Fridays was our drug-induced stupor," she says. "And I think there's this whole movement of men looking back and thinking, I actually don't want to look like that. There's been a backlash. That whole idea of not caring how you look is just old. There's something attractive about caring."

But men, most men, needed help caring. And so in 2007, four years into his job, Drexler decided it was time to help men. Not in a didactic or condescending way, and not in a way that tried to assign a look to them. Not in the sinister way Tom Cruise outfits his oblivious autistic brother Dustin Hoffman in Rain Man, propping him up in a gray suit and a point-collared shirt to count cards in Las Vegas. More like the way Ryan Gosling, wearing slim V-neck sweaters and suits wrapped tight, takes his new friend Steve Carell shopping in Crazy, Stupid, Love, which he does out of kindness and with carefree expertise, with no other motive than to help Carell's character, an American man whose desire to look presentable has lapsed, look and feel good again.

To begin executing his plan, Drexler first needed a store, someplace unusual, and one day his friend Andy Spade — creator of Jack Spade and husband of handbag legend Kate Spade — was walking in TriBeCa, one of the more fashionable and exclusive neighborhoods in Manhattan. He noticed that a bar called the Liquor Store, which had in fact once been a liquor store, had shuttered. It stood on a charming, crooked corner, and it looked the way it might have looked fifty years ago, or a hundred. It was cool. It was nostalgic. It had, to use a phrase from the cover of the first J. Crew catalog in the spring of 1983, significant tradition.

Drexler loved it. Maybe, he thought, in this tiny, nine-hundred-square-foot bar, J. Crew could do something different. Maybe it could sell men's clothes that didn't suck. And maybe men would care.

Shaniqwa Jarvis

"Men's apparel, by the way, is like any consumer product in the world," says Drexler. "Things happen because you feel it and you see it. Part of what we do in the consumer-sensitive business, as opposed to the commodity-price business, is see around the corner a little bit. That might mean buildings getting built with larger windows, which seems to be the norm today. Or the most valuable company in the world being a design-oriented company — Apple. [Whose board Drexler sits on.] Restaurants have become a space you feel comfortable in. And I think what's happened with our men's business has to do with the way J. Crew has always positioned itself: accessibility, friendly, nonintimidating in service, people, and price. How many men's companies, if you think about it, are nonintimidating?"

The bar Andy Spade saw became the Liquor Store. It would sell only men's clothes. There is no J. Crew sign out front — you could walk in, look around, and leave without ever knowing you were in a J. Crew. Nothing much was added to the interior — it still looks like a bar, complete with bottles of bourbon and vodka behind the counter. The wood floors are scuffed. Piles of New Balance shoeboxes fill space under the bar next to sweaters. It's almost hard to walk, the place is so crammed with clothes. The cramming, though, has only to do with the physical smallness of the room. There actually are not that many clothes there compared with a normal store. And that's the idea. When it opened, people inside the company and out used words like curated and edited to describe the stock. Every piece was chosen carefully so that everything in the store went with everything else. It was more dream closet than retail store — everything in it could conceivably belong to the same man.

The Liquor Store changed everything — for the brand and, eventually, for a good chunk of the men's-wear market. Todd Snyder, who was the head men's-wear designer at J. Crew in 2007, remembers the excitement. "The Liquor Store was a defining moment," he says. "It put a stake in the ground, and men could identify it and relate to it." Snyder left J. Crew in 2008, the year the store opened, to start his own namesake label, but he still reveres Drexler. "Everywhere I go — Tokyo, London, L.A. — I see the influence of the Liquor Store. It revolutionized not only J. Crew but men's-wear in general."

The new store and the new clothing in it were traditional without being derivative, fashionable without being fashiony, timely without being trendy. In 2007, Mad Men premiered and reminded Americans of a time when men — ambitious, successful men — wore suits and ties to work, and a year later J. Crew was there with tie bars, shiny dress shoes, and a new suit called the Ludlow, which — inadvertently but fortunately — echoed the streamlined aesthetic of the show and cost a mere $600. In 2009, during and after the recession, many men took to wearing older brands known for authenticity and heritage, and J. Crew was there, having already partnered with Red Wing (boots), Alden (shoes), Ray-Ban (sunglasses), and other labels that had some history behind them. Around 2011, just as Boardwalk Empire took off and set in motion a drive toward ballsier patterns and colors, J. Crew was there with brightly colored pants, bold shirts, and an expanded line of tailoring that included complicated patterns and double-breasted cuts.

Gradually, on its Web site and in its catalogs, the brand began stretching the limits of sartorial convention and in some cases casting them mercifully off. "Yes, you can do velvet," one 2012 catalog read, referring to a sport coat. "Just wear it with a little irony, like jeans and a chambray shirt." On the next page, a model wore a Ludlow tuxedo — yes, J. Crew now even sold tuxedos — without socks. Jack O'Connor, the men's style director and a driving force behind much of this instruction and inspiration, remembers the response. "We started doing a chambray shirt maybe five years ago," says O'Connor. "Then we started using it almost the way you would use an oxford shirt, and it got to the point where we were showing it with a suit. There was something that just clicked — everybody responded to that high/low look of work wear combined with tailored clothing."

"Taking a jacket and pairing it with jeans or wearing wing tips with jeans — it's like a chef taking the same ingredients and mixing them in a different way," says Snyder. "That's new. Or at least it was new a few years ago."

Shaniqwa Jarvis

It's hard to underestimate the importance of the Ludlow suit to the success of J. Crew's transformation. Its lapel is two and a half inches, about a half-inch skinnier than most suits', which gave it a look that was both contemporary and throwback. The padding inside the front of the jacket floated neatly among overlapping layers of horsehair and other fabrics so that it rested naturally over a man's chest. (In cheaper jackets, the interior padding is often glued down and makes a man look like a box.) There wasn't a lot of extra fabric in the sleeves, so your arms weren't swimming in folds. And when you buttoned the jacket, the sides cinched in just a little rather than maintaining the straight-down shape they might have in, say, the 1990s. As more and more men tried it on, they felt suddenly, and dramatically, more comfortable in their clothes.

One potential problem was that when the Liquor Store opened and the Ludlow was introduced, the economy was tanking. ("It was toilet time," Drexler recalls.) But J. Crew began to actually raise prices on its men's line. The company known for $52 roll-neck sweaters and $38 dress shirts was now selling a worsted-wool suit jacket for $400 and tailored wool pants for $200. But even as the recession wore on, the new line of men's clothes sold out routinely, often at speeds that took the company by surprise, and the success proved what many men already knew: They will pay a little more if they think it's worth the price. The Ludlow jacket, expertly tailored and manufactured from Italian and Irish fabrics at some of the finest factories in China (Drexler: "A lot of people don't know: There are fine factories in China"), starts today at $278, and the pants at $148. That's a little more than the sale rack at Men's Wearhouse, probably, but for the fit and feel and quality of the garment, it's a bargain.

At a meeting in Drexler's office recently, he told twenty-five members of his staff — he has a large office, which isn't really an office at all but a corner of the open-floor-plan headquarters — why he thinks certain things work in the fickle business of designing clothes. "I have a puppy at home," he said softly, and the chatter at the meeting died immediately. "I would think that in the last thousands of years of puppies, they always like the same things, the same toys to chew on. Your fingers." He was talking about consistency. Predictability. He happened to be looking at a picture of a women's shirt that had glitter on it — "Girls always like glitter" was his punchline — but he could have been talking about why men like the clean look of the Ludlow suit. Or why J. Crew has chosen to partner with companies that make things J. Crew concedes it can't improve upon. "Mickey is really good at identifying something and making money at it," says Snyder with a laugh that reveals admiration and mystification.

Colin Tunstall runs a three-year-old clothing company called Saturdays Surf NYC. Someone from J. Crew spotted a Saturdays T-shirt in 2010, a partnership was forged, and suddenly the company's apparel was selling out on jcrew.com. "They've created this brand matrix of heritage brands and up-and-coming brands like ours, which they mix in with their own clothes," says Tunstall. "At the end of the day, they just make and sell good clothes, and because of their size they can sell the clothes at prices that are pretty accessible. If they didn't make good clothes, they wouldn't have the sales. And if they didn't have the sales, this whole thing" — the great J. Crew men's-wear experiment — "wouldn't have lasted."

Sitting in his office, Drexler says, "We went from a commodity men's business" — selling as many pocket tees as possible to as many men as possible, chockablock, like the Gap — "to one that says, Okay, what do guys want to wear, how do they look, and How. Can. We. Serve. Them. Better." He raps his knuckles on the table with each of those last six words.

Shaniqwa Jarvis

A man from Holland stands in his office at J. Crew, one foot behind the other, each in a tawny leather boot under jeans casually but perfectly rolled up once at the ankle, and stares at the floor. To be more precise, he is staring at a pile of things that he hopes will inspire him as he does his job. This has been his office for the nearly five years he has been the head men's-wear designer for J. Crew — he took over for Snyder in 2008. He loves his job. He reveals this in little moments, like the way he starts talking faster when describing the careful construction of the Ludlow suit jacket.

The man's name is Frank Muytjens. He is tall and trim and elfish, and his bright eyes, behind thick, black glasses, dance across the flotsam assembled on his floor, including: a puffy winter vest, dark green with a dirt-colored band across the shoulders, that takes you back to the American suburb circa 1981; a hardcover volume of work by the modernist photographer Paul Strand; a green French military duffel bag in a clump; old travel brochures; shirts and shorts and pants in shades of teal and olive, overlapping like papier-mâché; and a 1965 black-and-white portrait of Michael Caine, an unlit cigarette hanging straight down his chin.

Muytjens collects these items from vintage markets and stores around the world. Then he stares at them on his floor for weeks and weeks. And eventually the stuff in the pile meshes together to become the seed of a new season of clothing. This particular pile will inspire the fall 2013 and spring 2014 J. Crew men's collections.

"Guys like old, comfortable things. Everything you buy needs to feel as if you had it already. We find these beautiful vintage military pieces, and we look at the functional details — we're geeks like that," he says, referring to the young men outside his office who make up the design team. "It's what makes our jobs so interesting. And then every season you tweak everything a little bit and take it to the next level without losing sight of what our guy wants."

Some of the guys on Frank's team fly-fish or snowboard together. One is preparing to climb Mount Kilimanjaro. "It's a very earthy bunch," he says. "That's what I like about them. They like fashion but without being too loud about it. You have to look at them twice before you realize how well they put things together."

That, essentially, is what J. Crew men's clothing looks like now: You have to look twice to understand how perfectly precise it is, why it fits so well, and why it looks the way most men want to look, whether they realize it or not.

"There's a sense of ... how do you call that?" Muytjens speaks perfect English with a melodic Dutch accent, but he's searching for a word. He pronounces um like am as he paces around his office, stepping over a pair of shorts. "Am, am, am ..." He looks at some notes on his desk that he typed in preparation for this conversation. "Ahh! I can't find it. Am. Am." He raps the paper with his fingers a few times in frustration. "Am. Oh, my God, I'm totally losing my mind."

He keeps talking, moving on to other things, but his annoyance with himself creases across his face.

"I can't think of that word! I'm sorrryyyy!"

Then he puts his chin in the crook of his fingers and stares at the pile of inspiration on his floor. His head pops up.

"Nostalgic. Nostalgic. It's up to us to look at the past and then do it in the present tense."

A man squats before a low wood table, sorting striped ties in bright colors, like penny-candy swizzle sticks. He works here, at the Ludlow Shop, just a few blocks from the Liquor Store. The Liquor Store couldn't contain the success of the suit. Now you can buy the Ludlow in its very own dedicated store, in Italian worsted wool, Irish linen, Japanese seersucker, glen-plaid Italian wool, or Italian chino. They all fit the same. The man is clean-shaven, shoes shined, unhurried. He nods when you walk in, gives enough of a smile to signal that he's happy to help if you want. He doesn't put down the ties and run over to you. But when you approach the wall of suits made with linen from Baird McNutt, an Irish mill that's been in operation since 1912, he stands and offers to get your size, which he guesses correctly, from the back room.

There's a reason you came in. You remember when J. Crew first appeared, in the eighties. It was the first brand you ever wore on purpose. Before that, clothes were just clothes — your mother bought them. But when you and your brother and sisters flipped through those catalogs at the kitchen table, you saw things you wanted. A sweater. A barn jacket. A plaid flannel shirt. Not just any things. These things. No one told you to wear them. But when you did, you liked them. Now you need not a roll-neck sweater for school but a suit for work — for life. And it's here. That's why you came in.

The man brings a suit in your size, and you try it on. The first thing you notice is how soft it is. When you button the front button, you feel a comfortable tug at the sides of your torso. The pants break just a hair over your shoes. The man stands off to the side a little, nodding. The suit fits as if it were made for you, as if it had been tailored specifically for you, right here in this tiny store, with its skinny shirts and its tailored Italian wool suits for $600. And you, a regular American man who walked in off the street, feel good.

Ryan D'Agostino Ryan D'Agostino is Editorial Director, Projects at Hearst, and previously served as Editor-in-Chief at Popular Mechanics and Esquire's Articles Editor.

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