How to Style Men's Shoes for Fall: Tips and Ideas

How to Style Men’s Shoes for Fall: Tips and Ideas

Men’s shoes can make or break an outfit, especially as the season changes. The proper footwear can add a touch of class to a casual look, and the cooler temperatures make fall the perfect time to rock some of the harder-wearing styles. Save the light canvas sneakers for spring and summer and opt for something more weather-ready, like chukka boots. These ankle-length lace-ups balance casualness and formality perfectly.


As summer fades, trade your canvas slip-ons for dapper leather shoes. Oxfords—also known as balmorals—are a men’s wardrobe staple, and they’re great for fall since they pair well with slim jeans or a casual suit. Look for black, brown leather Oxfords that suit your simple, dressier looks. Try a pair of chukka boots if you want something less formal but still sophisticated. These ankle-length boots are typically made from long-lasting materials like leather and suede. They also go well with a tweed suit or a dark wool button-down shirt. Every man’s closet needs a pair of sleek leather sneakers. Sneakers are a roll-over from the summer and can be worn throughout autumn. Check out a minimalist style or a more rugged option. Both styles work perfectly with slim jeans or cuffed chinos. They’re also ideal for a casual lunch with a co-worker or a weekend walk around the park.


Fall 2023 shoe trends are the season to swap out summery flip-flops for closed-toe shoes that provide warmth and security for walking outdoors. Whether you want to add a suede Chelsea boot or a simple leather shoe to your wardrobe, look for a weather-ready material like treated leather that’s easy to clean and resists water damage. Men’s sneakers are great for casual wear all year, but they shine in autumn. If you’re wearing them with linen pants, look for dark brown or black shoes that will complement the natural color of the linen.

The moccasin is to fall what the boat shoe is to summer, and it’s a must-have for men who love laid-back style. Look for a suede moc from a trusted brand that pairs well with everything from a camp-collar California-leaning outfit to a plain tee and jeans combo. If you plan to wear your mocs outside, protect them with a waterproof suede protector and keep an all-weather jacket in your car, just in case.


As the sun goes down, you’ll want to put away the flip-flops and pull on closed-toed shoes. If it’s rainy where you live, opt for waterproof and grippy options made of treated leather or rubber. Oxfords and Derbies are good choices if you’re looking for dressier shoes. Brogues are a specific form of oxfords and derbies that feature ornamental punctures on the shoe’s leather. You can find brogues in the quarter (along the toe cap, it seems), half, and full styles. They’re a great option with pressed slacks and a burgundy button-up shirt. If you prefer casual shoes, chukka boots work well for fall. Opt for a traditional leather silhouette or suede options. Or go for hybrid shoes. Hybrid shoes are a cross between dress shoes and sneakers and offer more support and grip than sneakers while retaining the sleek look of dress shoes.

Combat Boots

Fall means colder weather, and it’s time to replace your summer footwear with sturdy boots. Whether you opt for suede or tanned leather, shoes made of weather-ready materials will keep you comfortable as the temperature dips. If you want to go casual, chukka boots are a stylish option. These ankle-length, lace-up shoes are often made of long-lasting fabrics like leather and suede. They’re easy to style with slim grey jeans and a simple white T-shirt. Try a pair of combat boots if you want a more rugged look. Pairing them with relaxed athletic shorts and a logo T-shirt gives you a classic 90s style.

Regarding men’s boots, color matters; generally speaking, black boots are more formal than brown pairs, and it’s best to match your shoes to your belt and any other leather accessories you wear (like a watch). Complementary contrast is also essential: Dark colors should be worn with relaxed pants, and lighter colors should be paired with warm ones.

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