To understand how far luxury sportswear has come in this country, consider this: Tom Ford, the undisputed kingpin of black tie, the man whose mastery of Savile Row–level dressing is so dead-on he became James Bond's tailor, showed two—count 'em: one, two—suits for his fall 2014 presentation in London. Making up for the deficit were preposterously soft cashmere sweaters, a fur-lined bomber jacket, and flawlessly tailored cords—essentially, all the new status symbols of the young and moneyed.

It's a seismic shift for a designer who swore he'd never churn out a sneaker, then did just that, perhaps after realizing his own customers (grown men!) were looking sharp as shit in their white Stan Smiths worn with a $3,000 overcoat or a pair of chinos that hang perfectly because some guy in Italy is using the kind of meticulous craftsmanship that was once reserved for the shoulder of a jacket.

There was a time not long ago when men flush with cash kept their "dress shoes" in a tissue-lined box waiting for a work trip or, you know, a funeral. Now you see guys wearing their Church's lace-ups (and everything else shown here) throughout the week—whether it's walking around Chelsea on a Saturday or to a power lunch on a Wednesday. "The nine-to-five uniform is becoming a thing of the past," says designer Michael Kors. "People are going from the gym to a board meeting to a drink with friends to a dinner date. Men want a wardrobe that can do everything and go anywhere." And with the advent of looser dress codes, mobile offices, and the handful of fashion-conscious tech giants (think Kickstarter's Perry Chen or Twitter's Jack Dorsey) who are scrubbing our brains of clichés like the programmer proudly flaunting the hoodie he purchased from a midwestern mall circa American Pie, dressing well no longer means reflexively putting on a shirt and tie. "It used to be, you bought an expensive suit to show that you'd arrived," says Jay Vosoghi, creative director of the Italian label Boglioli. "Today a guy may spend just as much money on a pair of chinos or a chambray shirt or a pair of sneakers. Today there's value in these pieces."

To walk into Brunello Cucinelli's West Village store, a beige-drenched temple of cashmere, is to fully comprehend what the designer calls "a luxury, chic, sporty style," It's an ethos/marketing strategy that embraces the blurring of the lines between a man's weekend and work wardrobes. "A top-notch blazer with a special pocket square can be paired up with cargo pants," Cucinelli says. "It confers a very young and special look."

Still, it's not that the art of suiting has been rendered moot. "The thing is, we're selling suits," Vosoghi says. "But how are our guys wearing it? With a white shirt and a red tie? I don't think so." In other words: Wear a suit, just don't look like one.

Pictured, top:

1. Coat ($3,100) by Salvatore Ferragamo. Sweater ($1,070) by Exemplaire. Jeans ($230) by Acne Studios. Sneakers ($55) by Converse.

2. Jacket ($950) by Calvin Klein Collection. Shirt ($350) by Massimo Alba. Jeans ($178) by 7 for All Mankind. Shoes ($470) by Mr. Hare.

3. Blazer ($4,895) by Boglioli. Sweater ($225) by Gant Rugger. Shirt ($280) by Officine Generale. Pants ($770) by Brunello Cucinelli. Boots ($1,025) by Hermès.

Pictured, bottom:

4. Jacket ($7,000) by Bally. Sweater ($995) by Orley. Pants ($520) by Canali. Shoes ($800) by Church's.

5. Robe ($550) by Robert Geller. Sweater ($895) by Marc Jacobs Collection. Pants ($540) by Bottega Veneta. Sneakers ($790) by Tom Ford.

6. Jacket ($345) by Patrik Ervell. Shirt ($195) by Schnayderman's. Pants ($325) by Boglioli. Sneakers ($410) by Common Projects.

7. Sweatshirt ($1,980) by Valentino. T-shirt ($95) by Jardine. Jeans ($231) by Our Legacy. Shoes ($845) by Emporio Armani.

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