Mind and Body

The 8 Best Fall Boots For Men

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by Christina Wood and Kate Miller
Originally Published: 
Relaxed scene of a man wearing brown leather Chelsea boots sitting in a sun room in front of an open...
Catherine Falls Commercial/Moment/Getty Images

When temperatures drop in fall, it’s essential to have the right footwear on hand — nobody wants to wear worn-out boots that aren’t equipped for the season’s damp weather. But if you’ve ever invested in a pair of really nice boots only to continue to reach for that beater pair in your closet, there’s a psychological reason for it. A series of experiments found that once you deem an item “special,” the need to keep it protected can lead to never actually using it. So, in order to find the best fall boots for men, it’s important to find a pair that looks great but doesn’t feel overly precious. All the boots here are comfortable, ready for cool weather, and stylish — not to mention decidedly wearable.

From chukka boots that look good transitioning from the office to a night out to lug-soled boots that add grit without a second thought, there’s a boot here for any occasion, no matter what’s on your autumn itinerary. You’ll also find boots at all different price points so you can replace your beater boots without fear of draining your wallet.

We shopped so you don’t have to… here are our picks for your feet this fall.

1. Some comfortable chukka boots

It’s pretty hard to go wrong with this chukka boot. It’s comfortable (from comfort-brand Clark’s), easy to slip on and tie, and stylish. The all-leather upper is available in a range of colors that are so awesome, muted, and perfect for boots that you are going to have a hard time choosing. “Great fall boot,” one reviewer reported. “Everyday these boots get more comfortable, can tell I am going to love them as the leather softens.”

  • Available sizes: 7 — 15 (and in select wide sizes)

2. These polished lace-up boots for looking sharp

Can’t decide if you want some bad-ass motorcycle boots or something you can wear to a wedding? These lace-up boots walk the line between those two extremes so well that you come out the other side looking like some sort of elegant James Bond-meets-Mad Max mashup that’s sexy AF. You might want to get a nice date-shirt to go with these because there will be dates.

Comfort, class, and tough-guy sexy all from a pair of boots? You betcha! This is the stuff.

  • Available sizes: 6 — 14 (and in half and wide sizes)

3. This budget-friendly pair of Chelsea boots

For an under-$35 price tag, the quality of these Chelsea boots is astonishingly good. Made from synthetic leather, these slip-on boots look stylish enough to wear out for drinks, but the sturdy lug sole is ready to handle something more intrepid. “I have always loved this style of boot for yard/shop work,” one reviewer noted. “Finding these at a good price made it a no-brainer to pick up a pair!”

  • Available sizes: 7 — 13

4. A pair of sturdy hiking boots

Does your fall involve trails? Hiking while you peep at leaves? Paths that might not be raked or dry or anywhere near civilization?

That’s a great way to live.

And this is a great pair of shoes to live in while you do it. Comfortable, waterproof, all leather so the fit will keep improving, these boots are great for a Maine trail or a Portland wedding… or just to complete your sexy lumberjack look.

  • Available sizes: 5 — 15 (and in half sizes and wide and narrow sizes)

5. These affordable work boots for everyday

Whether you’re planning on hitting the trail or you’re donning these for work, these hiking boots are rugged enough to handle whatever you’re throwing at them. The genuine leather upper promises to get better over time and the memory foam insoles are designed to be cushy and breathable. “Love these boots, my favorite ones ever,” one shopper noted. “Very light and literally as comfortable as athletic shoes.”

  • Available sizes: 7 — 16 (and in select half sizes)

6. A pair of classic duck boots with thermal lining

Fall can bring with it some seriously wet, soggy days — forget about cold feet when you’re trying to get on with your day. Enter the rugged Sperry Avenue duck boot. It features a water-resistant leather upper and lugged rubber sole; plus, it has a warm thermal lining around the ankle (but several reviewers noted that they still paired it with thick socks for more total insulation). The cushy foam insole keeps things comfortable. Consider it the total package. Not surprisingly, more than 5,000 Amazon reviewers have weighed in on this pick, with one noting, “These are my go to boot for yard work or walking around the woods.”

  • Available sizes: 7 — 13 (and in select half sizes)

7. These Western boots for the modern cowboy

You work hard, and don’t need to get hurt while you do it. You head into the brush on a regular basis and don’t need to get bit by a snake while you are there. You are, essentially, a modern cowboy with your always-outdoors-doing-hard-work lifestyle. You probably already own a pair of these, if that’s your life for real. But a new pair of Western boots won’t do you any harm and your date will be pleased to see you in something clean for once. These are all leather and they will get the job—however manly—done.

  • Available sizes: 7 — 13 (and in half and wide sizes)

8. Some classic Docs you’ll own for years

Can over 6,000 Amazon reviewers be wrong about these Doc Martens? They are a classic for a reason. They kick ass, they are comfortable, and they last forever.

They also come in so many colors you can have a different pair for every persona you sport. Even if you have more characters in your multiple peronality disorder than Fortnite.

You have always wanted a pair of these. Here you go! Pick your color and go into fall wearing these!

  • Available sizes: 5 — 11

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