Boots for Fall

You’ve heard the term “suited and booted”. It’s been part of the menswear nomenclature for years, and for good reason. Summer and the days of flip flops, canvas sneakers, and slip-ons are over. Fall means cooler temperatures and more precipitation.

It’s time to wrap up your ankles, insulate your toes and waterproof your heels. Whether your uniform is a gray flannel suit or denim overalls, your boots should be made of the best materials available — leather and rubber — while standing up to the elements in style.

Here, we discuss a few options to keep you looking good and warm today, and well into the winter. Get ready to lace em’ up.

Wolverine 1000 Mile Boot | $310, Amazon

This series of Wolverine boots are called 1000 Mile’s for a reason. Soft wearing and hard working Horween leather make this a great choice for the man of leisure who enjoys the clean and polished look.

Style Tip

Although they’re made for the field, don’t be afraid to wear them even if you’re a city slicker. Just don’t tuck your pants into them.


$139, LL Bean

The ultimate marriage of form and function. The combination of waterproof waxed canvas and the stacked heel give this iconic boot from Maine a great name. Wear them during monsoon season.

Red Wing Beckman
$320, Amazon

Red Bull may give you wings, but these are the real deal. Red Wings are the quintessential “shit kickers”—but stylish. Made of the best leathers and materials Red Wings have a long heritage of working just as hard as the man that wears them. The Beckman is a classic example.

Lands End Canvas Crosby Moc Toe
$99, Lands End Canvas

Boots at the office? You can, and you should. This is a great option for flannel suits and corduroy trousers. Clean, smooth and in a warm chestnut brown color they’re a great way to look good at the office while being appropriate for the season.

Style Tip

Don’t be afraid of contrast. Wear your bean boots with a rugged tailored Tweed blazer or with a tie and button down shirt. Dressing up while you’re dressed down is always a good way to go.

Style Tip

While a leather sole is great for most conditions these won’t do well on ice or in snow. Stick with rubber, waxed canvas and Vibram for inclement weather.

Longtime Favorites

Check out our reviews of the Frye Dakota Mid-lace and the Red Wing 870.

leather boot care
Protect Your Boots from Winter

Check out our guide to caring for your leather boots from the winter elements.

leather boot care

For an affordable, American-made alternative, check out the 814 by Thorogood, shown here in Tobacco.

$120, Amazon

Hat-tip to Perry in the comments for the heads up!

This post may contain affiliate links, read about our editorial promise
Grant Harris

Grant Harris is Owner & Chief Style Consultant at Image Granted; a Washington, DC based Image Consulting Company dedicated to solving the complex image, style & fashion issues of today's professional man. He has a healthy obsession with socks. Follow him on Twitter & Facebook.