Must-Have Men’s Shoes for Fall for Every Occasion

When the leaves turn yellow and the mornings get chilly, your wardrobe must adapt to the season. Put away the flip-flops and Crocs and invest in quality footwear for fall.

Derby shoes are slightly less formal than oxfords and can be worn with suit pants and a tailored shirt for a dapper ensemble. Go for leather for a dressier look or suede for a casual vibe.


Oxfords, one of the most classic men’s shoes for fall, are a mainstay for traditional dress attire. They are a great alternative to Derbies for more formal occasions or when you want to smarten up jeans and casual chinos. Choose an Oxford, a versatile shoe that pairs well with a suit and tie or casual pants and a blazer.

Alternatively, you can also opt for the whole-cut Oxford, which is less formal, has no decorative perforations, and is made from a single piece of museum calf leather to create an elegant, simple, and sophisticated look.

For something a little more casual, opt for a pair of two-tone spectators or saddle shoes, which are less traditional but work well with jeans and corduroy trousers. If you want to be even more fashion-forward, opt for a pair of Chelsea boots with an elastic panel on the sides for easy pulling on and off. Try pairing cognac brown Chelsea boots with a knee-length cable-knit sweater and tailored wool blazer for an outfit that will envy the office.

Derby Shoes

Derby shoes are a more casual take on the Oxford shoe. They are essentially the same but with open lacing where quarters are stitched on top of the vamp instead of underneath. This allows for a slightly roomier instep and also makes them less binding. They’re great for gentlemen with a high instep who find the closed lacing of an Oxford to be constricting.

They are commonly found in black or brown leather with a variety of options for embellishment like suede and broguing. Broguing refers to the tiny perforations that decorate the surface of a Derby and can range from simple designs applied to only the toe area to full brogue detailing covering the entire shoe.

Though not traditionally worn as a formal evening shoe, it is expected to see derbies worn with tuxedos in certain parts of Continental Europe. 

Combat Boots

Whether you’re an avid hiker or want a pair of sturdy boots that will help you stomp through the piles of wet leaves October tends to bring, a pair of combat-style shoes is a great option. They’re a ruggedly handsome and durable choice for fall and can easily be worn to work, school, or other occasions requiring a sturdy yet polished look.

In the 1960s, the military began issuing shined black leather combat boots (“jump boots”) to equip soldiers in jungle and desert environments. These boots departed from the traditional brown leather combat boots, which the US Army still used for general duty wear.

Outside the military, combat boots have been popularized by icons like iconoclasts and punk rockers who incorporated the military-inspired silhouette into their streetwear looks. 


A must-have for any stylish man’s wardrobe, brogues have come a long way since their humble origins as country footwear. The punch-hole design, originally intended to drain water from the soaked feet of outdoor workers, has become a hallmark of the style. Plenty of options are available with four different toe cap styles (full or wingtip, half, and quarter brogues) and four closures (Oxford, Derby, ghillie, and monk).

The best brogues are dressy enough to wear with a worsted suit and casual enough to work with jeans or chinos. On the lower end of formality, chukka boots are a good option for fall and can be worn with dark-wash denim or a simple tee. For something even more casual, slippers crafted from sherpa or wool can add warmth and style to your at-home attire.



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