Fall and Winter Boots: My Favorite Styles

With autumn here and winter just around the corner, it's time to break-out, or invest in, your boot game.

I’ve put together an abbreviated list of my top boot choices for the colder months using my own collection to help you decide which style fits the bill.



The general relaxation of the American dress code paired with some spiffy offerings by workwear manufacturers means that there are several variations of work boots that are acceptable to wear casually these days.

Most notably, Red Wing 877’s, Red Wing Beckman, and Wolverine 1000 Mile boots. These are great to wear with jeans or chinos, but obviously not with a suit.

My choice is the Red Wing 877. A favorite of Ironworkers and vintage motorcyclists, these boots can take a beating and definitely get better with age.

Worn by Steve McQueen and Daryl from the Walking Dead. Doesn’t get much more badass than that.

Click here for the complete Work Boot article.



Originally created to be a waterproof hunting boot, the practicality and classic style of Bean boots (aka duck boots) make them a go-to for anyone dealing with wet, snowy conditions.

Many city dwellers choose these as their daily commuter kicks and then change to dress shoes at the office.

I personally wore a pair of these every day this past winter on a slushy, salty, grimy six-mile bicycle commute through downtown Chicago.

After a seemingly endless season of abuse, a simple wipe with a damp cloth and they look good as new!

Click here for the complete Duck Boot article.



Chukkas are 2-3 eyelet ankle boots, usually with a plain or moc-toe (moccasin). They’re the perfect combination of dressy and casual.

Smooth leather plain toe chukkas can be worn with anything from suits to jeans. Desert boots are a type of chukka that tend to have Crepe soles and more often than not, suede uppers.

A good example, although not suede, would be my pair from Clarks in their Beeswax finish.

Desert boots typically look best with jeans or chinos and are a great option for students and those working in a business casual office.

Also, only slightly less comfortable than slippers, these are my go-to shoes for 3+ mile treks.

Click here for the complete Chukka article.



When covered with pants, they’ll mostly look like your normal dress shoes.

The higher ankle makes them a good match for thick socks, providing more comfort in the colder months.

Just don’t make the mistake of thinking they’re built to handle the winter slush.

Generally speaking, they aren’t waterproof or insulated and road salt can destroy the fine leather uppers if left untreated. Also, if equipped with leather soles, traction will be an issue.

Despite these few shortcomings, dress boots will still hold up better than shoes in light rain and snow while looking a hell of a lot more appropriate for the office than a work boot.

I opted for Allen Edmonds Daltons in “Dark Chocolate”. These are worn on most days when it’s cold but not slushy.

I’d recommend getting these in a darker color so that, in the event they become stained or blistered from salt, any damage would be less noticeable than with a lighter color leather.


Of course, your personal style, work environment, and local weather conditions are going to affect your choices. Here are a couple generalized categories and recommendations for each.

Option #1 – All casual, all the time

For foul weather, grab yourself a pair of either work boots or duck boots and they’ll be able to handle anything you or Mother Nature can throw at them.

For mild weather (cool with light rain), chukkas should get the job done.

Option #2 – Business casual

You could probable get away with wearing most of these options at work, as long as you commit to keeping them fairly clean and presentable. Choose whatever tickles your fancy.

Option #3 – Corporate America

For the worst weather, wearing something like duck boots for the commute and then changing into proper dress shoes at the office is the only practical thing to do.

If slush, snow, and rock salt aren’t an issue, go ahead and rock the dress boots all day.

For mild weather, a dress boot or a smooth leather chukka with a leather sole should get you through the season.

I should note that I'll actually being doing a break-out post for each of these boot styles to show how and when to wear them.

Let me know in the comments if there any details you want me to geek out over in subsequent posts!

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  • Reply
    Harry Imrie Patton Clark IV
    September 26, 2016 at 5:51 pm

    What do you think of timberland boots and cowboy boots

    • Reply
      September 27, 2016 at 7:08 pm

      Cowboy boots aren’t my style but I know some companies put out some seriously good quality products and they work for guys in rural areas. I don’t think Timberland boots are really bad, but any pair that looks decent isn’t much less expensive than boots like Red Wings.

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