The Complete Fall Style Cheat Sheet

A guide to everything that matters in menswear after Labor Day: killer coats, trends worth trying, suits to own, and brands to know.

Jacket ($2,490) by Dsquared2. Sweater ($275) by T by Alexander Wang. Jeans ($345) by Simon Miller.

Page 1: Photographs, from top: By Nicholas Prakas (4); by Nicholas Prakas, styling by Eugene Tong, grooming by Dillon Pena, casting by Edward Kim at The Edit Desk; by Brad Bridgers, styling by Claire Tedaldi at Halley Resources; Getty Images (3). Page 2: Photographs, clockwise from top left: courtesy of designer; by Cathy Crawford, styling by Jody Cook; courtesy of designers (4). Page 3: Photographs, from top: courtesy of designers (4); by Nicholas Prakas, styling by Eugene Tong, grooming by Dillon Pena, casting by Edward Kim at the Edit Desk (2); inset photo courtesy of mptvimages.com; by Nicholas Prakas. Page 4: Photographs, from top: by Brad Bridgers; courtesy of each manufacturer (3); Getty Images.

Jacket ($2,490) by Dsquared2. Sweater ($275) by T by Alexander Wang. Jeans ($345) by Simon Miller.

We get that it's still sweltering outside and that buying a wool coat, even if it's unlined and cut from cashmere, is at the bottom of your to-do list. But admit it: At this point, after pulling out that pair of cotton khakis for the 300th time, aren't you just the tiniest bit curious about what's in store (and in stores, literally) come cooler months? On the following pages, we've made things ridiculously easy for you: Herein, the trends worth trying, the clothes to buy, and everything else worth knowing about men's fashion after Labor Day.

The Jean-Jacket Alternative

This fall, the cropped camel coat will be everywhere (and with good reason—it's a don't-think-about-it-just-wear-it kind of item). We especially like Dsquared2's interpretation (pictured, right): The relaxed shoulders, oversize pockets, and tortoiseshell buttons strike just the right balance between American workwear and prep.

$2,490; saksfifthavenue.com

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Page 1: Photographs, from top: By Nicholas Prakas (4); by Nicholas Prakas, styling by Eugene Tong, grooming by Dillon Pena, casting by Edward Kim at The Edit Desk; by Brad Bridgers, styling by Claire Tedaldi at Halley Resources; Getty Images (3). Page 2: Photographs, clockwise from top left: courtesy of designer; by Cathy Crawford, styling by Jody Cook; courtesy of designers (4). Page 3: Photographs, from top: courtesy of designers (4); by Nicholas Prakas, styling by Eugene Tong, grooming by Dillon Pena, casting by Edward Kim at the Edit Desk (2); inset photo courtesy of mptvimages.com; by Nicholas Prakas. Page 4: Photographs, from top: by Brad Bridgers; courtesy of each manufacturer (3); Getty Images.

The Two Ways to Do Three

By definition, perfectly tailored suits are—and should be—impossible to get wrong. But two of the riskier incarnations are making comebacks after falling out of favor: the three-piece and the three-button, both of which are looking more modern than ever this season.

To put it bluntly, three-button suits work best for vertically blessed men (the extra button shortens your torso). For those six feet and under, consider the three-button rolled to a two-button (3). The placement of the third button on the lapel renders it invisible when the blazer is left open.

With the three-piece, the goal is to avoid the overly fussy dandy look and instead follow the lead of Michael Caine circa Get Carter. Dior's somber take on pinstripes (6) and the navy Dunhill (5) seen here both adhere to the minimalist bent. Another option to consider? A soft-shouldered jacket. The unstructured cut of this windowpane plaid by Eidos (4) counterbalances the formality of a vest. When in doubt, look to model David Gandy, who's long worn the three-piece without looking like an extra in a bad gangster film. Proof that flawless tailoring and confidence go a long way.

1. Suit ($4,525) by Hermès. Shirt ($790) by Prada. Tie ($50) by Express. Shoes ($750) by Jimmy Choo.

2. Blazer ($2,275), pants ($775), and shoes ($695) by Giorgio Armani. Shirt ($860) by Prada. Tie ($155) by Ralph Lauren Black Label.

3. Suit ($6,630) and shirt ($570) by Brunello Cucinelli. Tie ($190) by Salvatore Ferragamo. Shoes ($785) by Grenson.

4. Suit ($2,130) by Eidos. Shirt ($660) by Dior Homme. Tie ($185) by Giorgio Armani. Shoes ($625) by Ermenegildo Zegna.

5. Suit ($3,575) by Dunhill. Shirt ($145) by HUGO. Tie ($75) by Berg & Berg. Shoes ($298) by Coach.

Page 1: Photographs, from top: By Nicholas Prakas (4); by Nicholas Prakas, styling by Eugene Tong, grooming by Dillon Pena, casting by Edward Kim at The Edit Desk; by Brad Bridgers, styling by Claire Tedaldi at Halley Resources; Getty Images (3). Page 2: Photographs, clockwise from top left: courtesy of designer; by Cathy Crawford, styling by Jody Cook; courtesy of designers (4). Page 3: Photographs, from top: courtesy of designers (4); by Nicholas Prakas, styling by Eugene Tong, grooming by Dillon Pena, casting by Edward Kim at the Edit Desk (2); inset photo courtesy of mptvimages.com; by Nicholas Prakas. Page 4: Photographs, from top: by Brad Bridgers; courtesy of each manufacturer (3); Getty Images.

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Page 1: Photographs, from top: By Nicholas Prakas (4); by Nicholas Prakas, styling by Eugene Tong, grooming by Dillon Pena, casting by Edward Kim at The Edit Desk; by Brad Bridgers, styling by Claire Tedaldi at Halley Resources; Getty Images (3). Page 2: Photographs, clockwise from top left: courtesy of designer; by Cathy Crawford, styling by Jody Cook; courtesy of designers (4). Page 3: Photographs, from top: courtesy of designers (4); by Nicholas Prakas, styling by Eugene Tong, grooming by Dillon Pena, casting by Edward Kim at the Edit Desk (2); inset photo courtesy of mptvimages.com; by Nicholas Prakas. Page 4: Photographs, from top: by Brad Bridgers; courtesy of each manufacturer (3); Getty Images.

Boots ($865) by Pierre Hardy. The Sole Survivor

The creeper (a play on the word crepe, the cheap rubber used to make army footwear in the forties) has continually been appropriated by stylish subcultures for more than 60 years. And like all good things in menswear, it's coming around again—Grenson, Ferragamo, and Pierre Hardy (who made our favorite pair, shown left) have perfected more subtle, real-world versions of the enduring wedge. Here, a brief charting of its evolution.

The 1950s

Inspired by military boots worn by British soldiers during WWII, shoemaker George Cox begins marketing streetwear versions in 1949. It's not long before "Teddy Boys" start wearing them with bolo ties, drainpipe trousers, and pompadours.

Page 1: Photographs, from top: By Nicholas Prakas (4); by Nicholas Prakas, styling by Eugene Tong, grooming by Dillon Pena, casting by Edward Kim at The Edit Desk; by Brad Bridgers, styling by Claire Tedaldi at Halley Resources; Getty Images (3). Page 2: Photographs, clockwise from top left: courtesy of designer; by Cathy Crawford, styling by Jody Cook; courtesy of designers (4). Page 3: Photographs, from top: courtesy of designers (4); by Nicholas Prakas, styling by Eugene Tong, grooming by Dillon Pena, casting by Edward Kim at the Edit Desk (2); inset photo courtesy of mptvimages.com; by Nicholas Prakas. Page 4: Photographs, from top: by Brad Bridgers; courtesy of each manufacturer (3); Getty Images.
Page 1: Photographs, from top: By Nicholas Prakas (4); by Nicholas Prakas, styling by Eugene Tong, grooming by Dillon Pena, casting by Edward Kim at The Edit Desk; by Brad Bridgers, styling by Claire Tedaldi at Halley Resources; Getty Images (3). Page 2: Photographs, clockwise from top left: courtesy of designer; by Cathy Crawford, styling by Jody Cook; courtesy of designers (4). Page 3: Photographs, from top: courtesy of designers (4); by Nicholas Prakas, styling by Eugene Tong, grooming by Dillon Pena, casting by Edward Kim at the Edit Desk (2); inset photo courtesy of mptvimages.com; by Nicholas Prakas. Page 4: Photographs, from top: by Brad Bridgers; courtesy of each manufacturer (3); Getty Images.

The 1970s

Punk's tastemakers Malcolm McLaren and Vivienne Westwood stock creepers at their London shop Sex—which are worn with tartan, safety pins, bondage pants, and ripped sweaters. The uniform becomes a sartorial "F you."

Above, left: Johnny Rotten in London in 1979.

The 1990s

Swing revivalist Brian Setzer jumps, jives, and wails in the iconic sole, channeling the big-band era.

Above, right: Brian Setzer in Atlantic City in 1998.

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*The Buyer's Shopping Guide *

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