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Our Favorite Men's Shoes for Fall

A man hiking in the woods with beautiful foliage all around

If you’re looking for the best men’s shoes for fall, we have plenty of stylish options to elevate this year’s autumn wardrobe. Well-dressed guys know that fall is easily the most fashionable season. The cool weather is perfect for layering and showcasing some of your favorite pieces, like sweaters, flannels, and of course, footwear in its many forms. Let’s take a look at some classic men’s casual fall shoes to add to your collection.

Everyday Boots

Casual boots and autumn attire go hand-in-hand. A pair of brown boots are so versatile all year round, but they work especially well alongside warm, foliage-inspired colors like orange, red, yellow, and beige. Black boots are another solid choice when shopping for men’s shoes for fall, as they look smart and match virtually any autumn outfit you can put together. In particular, we recommend Chelsea boots. They look incredible with jeans, khakis, or corduroys, ideally paired with a sweater.

Monk Straps

There’s something about monk straps that feels so cozy, bucolic, and well, autumny. While they’re technically dress shoes, monk straps are super versatile, and they work wonderfully alongside business casual staples like plaid shirts, khakis, and chinos. Well-fitting jeans, a polo shirt, and monk straps are another great casual look that’s comfortable yet sophisticated.


When shopping for men’s shoes for fall, be sure to keep comfort in mind. After all, the cool climate makes autumn the best time of year for long strolls. While sneakers are always a fine choice for outdoor adventures, we recommend chukkas for guys who want to keep their look sharp. Tan chukkas are iconic, and they work with virtually any outfit you throw at them. We also offer chukkas in a huge variety of unique colors if you want to stand out from the crowd.

Anything Leather

A guy wearing brown leather boots and cuffed jeans standing on autumn leaves

Genuine leather footwear is always a great choice for men’s casual fall shoes. Whether you’re at the office or in the woods, leather men’s shoes for fall deliver a timeless aesthetic that gets better and better with age — the more you wear them, the better they look (and feel). When it comes to autumn vibes, a pair of leather shoes or boots, cuffed selvedge jeans, and a flannel is about as good as it gets!

Save on Quality Footwear

These fall footwear essentials will treat you right, but fashion is personal, and the only rule is that there are no rules! We’re proud to offer hundreds of unique designs, so shop by style to find the kicks that fit your preferred autumn aesthetic. Our prices can’t be beat, and variety is the spice of life, so add all of your favorites to your collection. Get an amazing deal on men’s shoes for fall today!

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