Search for the best men’s autumn shoes can pretty overwhelming. During summer, you’d naturally float towards pairs that are made for the warmer weather in mind, while the winter is all about protecting yourself against the ice and the snow and all the other things that seem to happen in the British summertime too. Autumn very awkwardly sits right in the middle of these seasons, so you need to find shoes that are cosy (but not too cosy), waterproof (but not too waterproof), and grippy (but not too grippy).
With pumpkin spice lattes back on the menu and Christmas looming dangerously over our heads, in this guide, we’ll be going through some of the best men’s autumn shoes that you buy today, what occasions you should wear them for, and how you should actually wear them.
1 | Derby shoes
No autumn rotation is complete without a pair of Derby shoes. Also known as a Blucher, Gibson, or Lorne, this footwear option has been around for nearly two centuries and it hasn’t really changed much (if at all). Known for the way its eyelets are sewn directly on top of the vamp, this construction method, known as open lacing, is what makes these different from the classic Oxford shoe. So don’t get them mixed up.
Once worn by adventurers and hunters, Derby shoes are now the go-to shoe for fancy dinners, cocktail parties, and even weddings. Wear these with a blazer, a nice dress shirt, and a pair of smart trousers. You can also wear Derby shoes with denim jeans, but do this only if you really have to.
The pieces to buy:
2 | Chelsea boots
Believe it or not, Chelsea boots are one of the oldest footwear styles in history. Invented by Joseph Sparkes Hall (who was also Queen Victoria’s personal shoemaker) back in 1837, their overall design has pretty much remained exactly the same since. Characteristically, these are ankle-height and feature an elasticated panel on the sides, making them easy to pull on and off while on the go.
If you want to feel extra cosy this autumn, opt for a cognac brown colourway and pair it with cardigans, cable-knit sweaters, and very big coats (we’re talking Pedro Pascal at the Met Gala kinda big). In the ‘60s, Chelsea boots played a huge role in the British motorcycle scene, so denim jackets and pre-distressed selvedge jeans would go well too.
The pieces to buy:
3 | Combat boots
Punk is back, baby, and the return of this subculture has also sparked the rebirth of the iconic combat boot. Originally worn by the military (duh), around the ‘70s, punks and skinheads started rocking combat boots as a way to reject societal norms and rebel against authority. They’re also the perfect autumn shoe for those want some protection against the elements without the chunkiness of hiking boots.
