Choosing the right shoes for fall can be tricky, as summer footwear tends to float towards shoes made for warm weather, while winter footwear is all about protecting against ice and snow. Fortunately, several shoes work well in the transitional period between these seasons. Some boots have a unique look and offer a lot of ease when slipping them on and off.

Classic

No fall wardrobe is complete without a pair of classic leather shoes. Boots are the perfect option for men who want to add a touch of ruggedness to their formal look. Wingtips, also known as derby shoes, have open lacing that differentiates them from oxfords and allows them to be worn with a suit or pressed khakis for dressier occasions. Sneakers are another excellent fall shoe option for men. Depending on your style, you can wear sneakers with jeans or chinos, and the low-profile pairs easily slip under a wool overcoat or a winter parka.

Modern

Men’s shoes for fall is all about layering, meaning your footwear should reflect the season. Avoid cliches like flip-flops and Crocs, and choose something more sophisticated, like a pair of suede loafers. These shoes look just as stylish with jeans or chinos as a suit. You can also go full-on brogue for a bit of extra sartorial flair.

If you’re a first-timer, try a semi or quarter-brogue in a dark brown to ease your way into the world of classic leather shoes. For those men who love the outdoors, a good pair of hiking boots is essential. Look for rugged boots with grippy soles and a waterproof coating, then team them with your favorite outdoor gear to conquer your next hiking adventure. The best part is that your feet will stay warm and dry.

Simple

When temperatures cool, it’s time to swap out the light sneakers and sandals you wore all summer. Instead, choose sturdy leather boots that balance style with practicality. Look for options like chukkas or brogue dress boots. Consider brown suede shoes if you want to take your fall footwear game up a notch. If you’re looking for a more formal shoe, try wingtips, an alternative to standard oxfords and derbies.

They’re distinguished by ornamental punctures and pinhole designs that add visual interest to your outfit. The resurgence of punk and 90s fashion has also brought back combat boots. These rugged shoes are perfect for those wanting to escape the norms and express individuality. Pair them with distressed denim and a band T-shirt, then layer on a moto jacket. You’ll be ready to head out on a hike or hit up a concert in no time.

Comfortable

Shoes can make or break your wardrobe, and footwear can elevate even the most casual outfit. Regarding fall attire, the best shoes are often more rugged and masculine than you’ll wear in warmer seasons. Many styles are crafted from stiffer textiles like leather and suede.

A pair of rugged chukka boots will complement any autumn ensemble if you like the outdoorsy style. These ankle-height lace-up shoes are versatile for everyday wear yet stylish enough to partner with jeans and a flannel shirt. If grunge is more your thing, then you can pay tribute to Kurt Cobain by pairing a pair of black chucks with acid-wash jeans and a thick flannel.

The most classic options for formal footwear are oxford shoes (also known as balmorals). These sleek leather shoes are perfect for wearing to work or for a formal event. If you invest in this stylish shoe type, we recommend checking that you can wiggle your toes comfortably when trying them on.