The best in seasonal shopping.
 
Monk Straps
 
A modern menswear favorite with old school roots, the monk strap is a surprisingly versatile shoe. Sure, they're dapper and continental, but that doesn't mean they have to be worn with a suit. Give these slick kicks a casual twist by sporting them with your worn-in jeans or rumpled chinos. And feel free to show some sock—the bolder the better.

Becket Simonon,
$130

 
$
$$$
 
 

Wallin & Bros.,
$150

 
 

Cole Haan, $248

 

Allen Edmonds, $345

 

Billy Reid,
$395

 
Sneakers
Fall presents all sorts of opportunities to pull on some sneakers. Whether for more off-duty occasions like tailgating with buddies and casual outdoor dates, or simply to sport in a relaxed work environments, you want a pair that's simple, sleek and easily adaptable. From the high-end versions cut from premium leathers and hand-sewn in Italy to more approachable classic styles.
 

Epaulet, $275

$
$$$
 
 

Nike,
$70

 
 

Greats, $99

 

Adidas, $110

 

Common
Projects
,
$400

  •  
    The signature set of numbers on Common Projects' kicks denote that particular pair's style, size and color.
 
Chelsea Boots
Simple and streamlined, the chelsea boot—in all its stately elegance—is quintessentially British. And while it has a history as a mod staple back in London's swinging sixties, today they make for a boot that's as versatile as it is attractive. Whether you opt for polished leather or more seasonal suede, they go as well with a beaten-up pair of jeans as they do with a suit.
 

Ralph Lauren, $198

$
$$$
 
 

ASOS, $76

 
 

Andrew Marc, $178 / $107

 

Frye, $258

 

Grenson, $405

  •  
    The boots originated in the Victorian era, and were first used for horseback riding.
 
Suede Loafers
The loafer is an American classic that swept through academia back in the day, which is perhaps why it seems like such a fitting style for fall. But these aren't the loafers your dad wore back in the day. Today's are leaner and meaner than ever. Cut from an autumnal suede leather, the silhouette has been slimmed down and the details have been stepped up—from timeless hardware like Gucci's horse-bits to more of-the-moment additions like a red brick sole.

Rancourt, $290

 
$
$$$
 
 

Florsheim, $105

 
 

Barneys, $199

 

Alden, $486

 

Gucci, $530

  •  
    Anatomy of a Classic: Learn more about the Bass Weejun, celebrating nearly a century of shoe making.
 
Hikers
We'll just start off by saying that these aren't for everyone. But for guys who want some tough (yet comfortable) kicks to tackle the season's range of conditions, these hybrid hikers do the job and then some. They offer the durability and traction of a hiking boot with comfort and casualness of a tennis shoe.
 

Timberland,
$100

$
$$$
 
 

Nike, $90

 
 

New Balance, $100

 

Clae, $175

 

Filling Pieces, $212

 
  •  
    New Balance's 710 model is based on a hiking shoe developed for the brand by famed mountaineer Lou Whittaker.
 

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