Winnetka, Ill. - Wes Gordon stood at a discreet three or four feet from his client Jennifer Martay, running his fingers reflexively through his dense, wavy hair.
'Indulge me, I'm the designer,' he coaxed, all mischief, as Ms. Martay, a private-wealth manager, assessed her image in a full-length mirror, fretting over the length of a dress. That the dress had emerged on Mr. Gordon's fall runway, fetchingly sheared to mid-calf, failed to move her. 'My calves look too athletic in this,' she moaned.
'Your calves look great,' Mr. Gordon assured her, clearly nursing a hope that she might change her mind but too polite, or too shrewd, to put it to her plainly. Engagingly boyish and quietly dapper in a charcoal jacket and tattersall shirt, the designer knows his business after all, which, at a trunk show in Winnetka, Ill., earlier this fall, was to deftly tread the line between imposing his vision and bowing to his clients' concerns.
'You can see it instantly if a woman feels pretty,' he told a visitor. 'Then you move in.'
Yet as he worked the room at Neapolitan, an upscale boutique in this Chicago suburb's tree-lined, Tudor-timbered business district, Mr. Gordon showed no trace of hauteur or calculation. He greeted the streams of customers filing into the store on a blustery morning with the easy aplomb, though little of the grandness of his legendary predecessors: trunk show impresarios like Oscar de la Renta or the perennially affable Bill Blass, the latter a fixture at the galas of his socially prominent clients, addressing intimates as 'Babe,' coddling, jollying and gently wheedling them into his latest creations.
It's an art form that Mr. Gordon, 28, shows precocious signs of mastering. These days he is leading a handful of young designers who are doing their utmost to breathe gusts of life into a tradition that until recently had been all but laid to rest.
In the days of Mr. Blass, and again in the early 2000s, 'the trunk show was really about how to build a business,' said Mortimer Singer, the president and chief executive of Marvin Traub Associates, a retail consulting firm. 'New businesses are putting a different spin on that model, selling the customer not just the clothes, but an emotional experience.'
Mr. Gordon himself, whom Mr. Singer singled out as 'the one to watch,' has been quick to engage a new generation of affluent shoppers, many in their 40s, with a mix of playful banter, courtly attentiveness and, for all his youth, a lightly worn urbanity. Prized qualities at a time when, as Anna Wintour suggested in an episode of 'The Fashion Fund,' on the Ovation network, a talented newcomer needs to manifest plenty of polish and a personable presence to build or advance a career.
When Mr. Gordon founded his business five years ago, fresh from the prestigious Central Saint Martins design school in London and after-class internships with Tom Ford and Mr. de la Renta ('I'd stand and hand him pins,' he recalled), fashion was still reeling in the aftershock of the 2008 market collapse. 'Stores were very reluctant to place an order from a young designer,' he said.
Why not, then, take a page from fashion's past?
'Oscar, Bill, Donna Karan, Diane von Furstenberg - they were the masters,' Mr. Singer said. 'Their businesses were built in part by pounding the pavement, really getting in front of the customers and not being shy about it.'
Mr. Gordon is determined to follow a similar path, never mind that trunk shows, he said, 'can be a blessing and a curse.'
'When you're young and in the luxury category,' he said, 'you have to run eight times as fast to keep up. It's a privilege to hang within arm's reach of iconic luxury brands, but those brands have a tremendous heritage and incredible resources.'
'Yet when a woman walks into that store, she's holding you to the same standard,' said the designer, who works with six full-time employees in a whitewashed loft in the financial district. That disparity makes it all the more pressing, he said, 'to take advantage of every opportunity to engage with your client and use all the tools at your disposal to form a more personal connection.'
A camera-ready look doesn't hurt. At 6-foot-3, with a shock of sandy hair and even features, he is to his fans, as one customer in Winnetka remarked, 'a tall drink of water.' As useful, he knows, is mingling with the gratin at high-profile social events.
Mr. Gordon insists he is no gadabout. 'I'm not trying to do Alexander Wang,' he told Cathy Horyn, then the fashion critic of The New York Times, in 2011, and indeed, the designer, who retreats on weekends to his country house in Litchfield, Conn., has positioned himself as something of an anti-Wang, having turned his back on the downtown party scene.
He would have you believe he curls up most evenings with his spotted dog, Bird, immersed in an episode of 'Homeland.' Yet he was Zelig-like this fall, rubbing shoulders with the likes of Jeff Koons, Julian Schnabel and the collector Beth Rudin DeWoody at the Whitney Museum gala in November; only days earlier he was snapped in the company of Indre Rockefeller, Chloë Sevigny and Maria Elisabeth von Thurn und Taxis at a Cartier party.
He was at the CFDA/Vogue Fashion Fund cocktail party on the arm of the model Frankie Rayder. (A two-time contender for the award, Mr. Gordon, who didn't win, had no regrets, he said, the experience having raised his profile and sharpened his eye.) Late last month, he showed up at the Fashion Group International Night of Stars at Cipriani Wall Street.
Mr. Gordon is happy to share the spotlight with cultural potentates and the social swans he cultivates, but he prefers, he said, to engage with his 'ladies' on the selling floor. Lauren Santo Domingo, a founder of Moda Operandi, a website and virtual trunk show that affords users the privacy, and efficiency, of ordering clothes directly from the runways, has witnessed his low-key sales pitch. 'He combines a boyish charm with the manners of an older gentleman,' she said, in a way that harkens back to the days of Mr. Blass himself, 'when an association with the designer was quite fun - and shopping was a more social pursuit.'
In the palmy early 2000s, trunk shows magnetized customers with an engaging mix of theatrics and commerce, and a single event could generate sales in seven figures. Fashion die-hards used to dash into stores waving tear sheets from Women's Wear Daily to place dibs (and a 50 percent advance) on the coming season's sought-after styles, never mind that they would not arrive for a full four months.
Robert Burke, a luxury consultant and a former fashion director of Bergdorf Goodman, recalled that, in his time at the store, trunk show business sizzled. 'In 2001, we broke $1 million with Chanel,' he said. Trunk show sales peaked more than a decade ago, when Chanel took in $10.6 million at two New York shows, and Mr. de la Renta held three shows, each tallying sales of $1 million.
Times change. 'In major urban areas, shoppers don't put as much value on the entertainment factor of a trunk show,' Mr. Burke said. 'They go after the fastest, most effective way to get what they want.'
Many have turned to virtual trunk shows like those of Neiman Marcus, Net-a-Porter and, notably, Moda Operandi, which, observers argue, has played a role in rekindling interest in the conventional in-store model.
'It opened the eyes of a younger, moneyed customer,' Mr. Singer said. 'Maybe the designer will chat with you while he's pinning something. And you will have an emotional connection that adds significant value to the piece.'
Practically speaking, such by-invitation events can lend merchants an edge. 'They allow our best customers to view a better assortment from the designer than we would otherwise carry,' said Liz Rodbell, the president of Lord & Taylor and of Hudson's Bay in Canada - and give the store a risk-free chance to test the wares. 'Based on the immediate demand, we might do a broader business in the future.'
Still, designers tend to be the chief beneficiaries. As Ryan Lobo, a partner in Tome, a pared-down and sculptural women's line, explained, 'A trunk show gives the designer a degree of control, a chance to show the collection as we meant it to be seen, and immediate insight into the client's reactions.'
Mr. Gordon amplified: 'If you don't know these women, selling to them is kind of a shot in the dark.'
Earlier in his career, Mr. Gordon designed for an elusive ideal, working, as did Mr. Blass, from a cinematically fueled imagination. His muses, trailing a faintly patrician air, have included Lauren Bacall, the Champagne-tressed Carolyn Bessette Kennedy and Gwyneth Paltrow, who has, on occasion, graced his front row. He has consistently offered sumptuously embellished but increasingly streamlined coats, suits and dresses for clients like January Jones, Lena Dunham - and Michelle Obama, who, early in his career, wore a glittery houndstooth jacket he designed.
During his first seasons, some waved off Mr. Gordon's fantasy-driven designs as unapproachable, if not downright matronly. 'I remember saying to him, 'You're young; these clothes are very dressy,' ' Mark Holgate of Vogue told viewers in an episode of 'The Fashion Fund.' ' 'Make them for women of your generation.' '
In fact, a faintly louche south-of-Canal Street sensibility has filtered into Mr. Gordon's work. As it happens, he now makes downtown his weekday home, sharing a loft in TriBeCa with Paul Arnhold, his boyfriend of five years, a business student at Columbia University. Ms. Santo Domingo detects traces of the decadent '90s in some of his recent designs. Nothing costume-y, mind you, but as she noted, 'there is a lot of usage of the bias cut, slip dresses with oversize jackets, a spaghetti strap here or there.'
In Winnetka, customers warmed to Mr. Gordon's more youthful looks. Noticing the low-slung pockets of a slender evening dress, Ms. Martay, the banker, thrust her restless hands inside them. 'It's good to have something for the insecurities,' she said.
Missy Kedziour, a socially active mother of two, glanced at a somewhat theatrical fox-collared coat, finding it too rich. 'But I do need a fur,' she said, joshing. 'I think of myself as Gwyneth Paltrow in 'The Royal Tenenbaums.' '
Mr. Gordon shot back encouragingly, 'I see you more as Gwyneth in 'The Perfect Murder.' '
The furs stayed on the racks, but Mr. Gordon's wares, which sell for more than $500 for a top to $8,000 or more for an evening dress, otherwise performed robustly, generating more than $150,000 in combined fall styles and advance spring orders, according to Kelly Gordon, Neapolitan's owner.
As he talked, Mr. Gordon darted restlessly from fitting rooms to racks filled with costly frocks, shearlings and furs bearing labels like Marni, Altuzarra, J. Mendel and Alexander McQueen.
Exhausted and famished, having sipped a Diet Coke for lunch, he confided: 'At these events, you're on all the time. It's hard.'
Yet he is fueled by a conviction that, however energetic your performance, however winning your manner, you are only as compelling as your last collection.
'You are competing,' he said. 'If the customer takes 10 things into the fitting room, and only one of them is yours, you know in this business how tough it can be.'