Autumn brings a shift in weather, style, and footwear needs. As the leaves turn golden and the temperature drops, men everywhere are looking for the perfect boots that will provide both comfort and style. A good pair of boots is essential for navigating the unpredictable weather of autumn, from cool sunny days to rainy, blustery evenings. Choosing the right pair of boots isn’t just about fashion—it’s about functionality and comfort, too.
In this guide, we’ll explore the best boots for men this autumn season and cover a range of styles and price points. Whether you’re looking for something rugged for outdoor adventures, stylish for city life, or versatile enough to handle both, there’s a boot for you.
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Chelsea Boots: The Timeless Classic
Overview: Chelsea boots are a fall staple for men. With their sleek design and ankle-high fit, these boots offer both comfort and sophistication. They’re easy to slip on thanks to the elastic side panels, making them a great option for men on the go. Chelsea boots are versatile and can be paired with both casual outfits and more formal attire. Whether you’re heading to the office or meeting friends for a weekend brunch, Chelsea boots provide a polished look with minimal effort.
Top Picks:
- Blundstone 587 Rustic Brown Chelsea Boots
- Price: $199
- Why They Stand Out: Blundstone is known for its durable, no-nonsense boots, and the 587 model is no exception. Made with premium leather and featuring a comfortable cushioned footbed, these boots are ideal for autumn weather. The rustic brown color gives a rugged, yet polished look, and the water-resistant upper makes them great for rainy days.
- Common Projects Suede Chelsea Boots
- Price: $505
- Why They Stand Out: For those willing to invest in a high-end pair, Common Projects offers a luxurious suede option. These boots feature a slim, sleek design and are known for their craftsmanship and minimalist aesthetic. The suede material gives them a unique autumnal vibe, though care should be taken to protect them from moisture.
Styling Tip: Pair Chelsea boots with slim jeans or tailored trousers for a sharp, streamlined look.
Hiking Boots: Function Meets Fashion
Overview: Hiking boots aren’t just for the trail anymore. This autumn, hiking boots have made their way into mainstream fashion, blending ruggedness with style. They provide excellent support, warmth, and durability, making them a perfect choice for men who want boots that can handle both urban streets and outdoor excursions. Hiking boots are ideal for navigating unpredictable autumn terrain, whether you’re hiking in the woods or walking through city streets.
Top Picks:
- Danner Mountain Light Cascade
- Price: $430
- Why They Stand Out: Danner has a reputation for creating high-quality, durable boots, and the Mountain Light Cascade is no exception. These boots are made from full-grain leather and come with a Vibram outsole for added traction and stability. Perfect for men who enjoy hiking but want something stylish enough for everyday wear. The waterproof Gore-Tex lining is an added bonus for autumn’s rainy days.
- Merrell Moab 3 Mid Waterproof Hiking Boots
- Price: $145
- Why They Stand Out: If you’re looking for a more affordable option, the Merrell Moab 3 offers excellent value for money. These boots are known for their comfort, breathability, and waterproof design. They feature a contoured footbed that provides excellent support for long walks, and the durable rubber sole ensures great traction. Ideal for men who want reliable performance without breaking the bank.
Styling Tip: Hiking boots pair well with rugged denim or cargo pants for a casual, outdoorsy look. You can also wear them with a waxed jacket for added autumn style points.
Work Boots: Built for Durability
Overview: Work boots are designed to handle tough environments, but they’ve become popular as everyday wear for their rugged, masculine appeal. With their sturdy construction, thick soles, and protective toe caps, work boots are built to last through the wear and tear of daily life. They’re a great choice for men who need something tough and durable but also want boots that look good with their autumn wardrobe.
Top Picks:
- Timberland PRO 6-Inch Work Boots
- Price: $160
- Why They Stand Out: Timberland is synonymous with work boots, and their PRO 6-Inch model is a classic. Made with waterproof leather and featuring a padded collar for added comfort, these boots can handle just about anything autumn throws at them. They’re designed for men who need a functional, stylish boot for both work and casual wear.
- Red Wing Heritage Iron Ranger
- Price: $349
- Why They Stand Out: Red Wing’s Iron Ranger boots are iconic in the world of work boots. Made with premium leather and built to last, these boots offer superior durability and comfort. The Goodyear welt construction means they can be resoled, extending their lifespan. Their rugged design pairs well with jeans and flannel shirts, making them a great choice for casual autumn wear.
Styling Tip: For a classic workwear-inspired look, pair your boots with dark denim and a heavyweight flannel shirt.
Chukka Boots: Versatile and Comfortable
Overview: Chukka boots are ankle-high boots with a round toe and minimal lacing, often made from suede or leather. They offer a more casual and relaxed look compared to other styles but are still polished enough for a variety of settings. Chukka boots are a great option for men who want a lightweight, comfortable boot for autumn that can transition easily from day to night.
Top Picks:
- Clarks Desert Boot
- Price: $150
- Why They Stand Out: The Clarks Desert Boot is the original Chukka and remains one of the best options out there. Made from soft suede and featuring a crepe sole, these boots are incredibly comfortable and offer a relaxed, casual vibe. They’re ideal for autumn days when you want something easy to wear but still stylish.
- Thursday Boot Co. Scout Chukka
- Price: $149
- Why They Stand Out: Thursday Boot Co. offers a modern take on the Chukka with the Scout model. These boots feature water-resistant leather and a durable rubber sole, making them more rugged than the average Chukka. They’re a great option for men who want a boot that can handle both casual outings and more rugged adventures.
Styling Tip: Chukka boots pair well with chinos or rolled-up jeans for a laid-back, smart-casual look.
Combat Boots: Bold and Edgy
Overview: For men looking to make a statement this autumn, combat boots are a bold choice. With their lace-up design and thick soles, combat boots offer a tough, edgy look that pairs well with a variety of outfits. Originally designed for military use, these boots have become a fashion-forward choice for men who want something a little different.
Top Picks:
- Dr. Martens 1460 Combat Boots
- Price: $170
- Why They Stand Out: Dr. Martens is the go-to brand for combat boots, and their 1460 model is iconic. These boots are made from durable leather and feature the brand’s signature yellow stitching and air-cushioned sole. They’re comfortable, long-lasting, and perfect for men who want a boot with a bit of edge.
- Balmain Leather Combat Boots
- Price: $1,095
- Why They Stand Out: If you’re looking for something high-end, Balmain’s leather combat boots offer a luxurious take on the style. Made in Italy with premium leather, these boots feature a sleek, polished design that’s perfect for men who want to stand out. While they come with a hefty price tag, they’re a fashion statement that’s hard to ignore.
Styling Tip: Combat boots pair well with slim-fit jeans or leather jackets for a rebellious, urban look.
