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!

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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.


  • Reply October 10, 2011


    Those Wolverines are beautiful!

  • Reply October 11, 2011


    Try Thorogood boots as alternative to Wolverines and Red Wings. Less than half of the price and just as awesome (same leather, sole, etc.) throughout the year. I have a pair of 814s in Tobacco Gladiator and they’re gorgeous, even more beautiful after conditioning. And, as an added bonus, they’re made in the USA.

  • Reply October 11, 2011


    Perry, the Thorogood boots look awesome! I’ll look into reviewing them.

  • Reply October 11, 2011

    Grant Harris

    @Perry Great find!

  • Reply October 14, 2011


    Great boots. I love my Red Wing boots — I’ll probably be buried in them. I’ve also found my desert boots to be great for fall as well. You can’t go wrong with those.

  • Reply October 16, 2011


    Super helpful. What about coats?

  • Reply October 16, 2011


    Hey Sloan, You can check out this post Grant and I did here:

    Or stay tuned for a new one. 🙂

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  • Reply October 24, 2011


    Always a fan of Red Wings. Always.

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  • Reply November 8, 2011


    The new North Face Ballard 6″ winters are truly nice for < $200 too…

  • Reply January 14, 2012

    David P.

    Does anyone have any tips for keeping white soles on boots looking white/clean? I have a pair of Thorogood 814’s in tobacco brown (amazing boots and I highly recommend them), and despite wiping the sole down after every wear, certain spots are turning grayish-brown. Thanks in advance.

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  • Reply August 31, 2012


    I am a big fan of the Doc Marten’s 1460 in brown leather. I’ve had a pair for about 2 years that have served me well. They’re very comfortable and have a nice look when paired with jeans. I’ve gotten lots of compliments on them.

  • Reply March 20, 2015


    How do you feel on CAT’s classic nobuk workboots for a date?

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