Up your fall footwear game with our pick of the best weather-ready styles for men
The best men's shoes for autumn are the ones that complement your fall outfits, but not at the expense of comfort or practicality. This is a time of change, and swapping your summer sneakers for something more seasonally appropriate is a big part of your sartorial adaptation. Gone are the days of suede loafers and bright-white canvas sneakers – these unpredictable months call for a sturdier, more robust type of shoe. And something that won’t turn heel at the first sight of rain.
So, what are your options? Thankfully, there are quite a few. From the time-honoured classics to the new footwear styles blending fashion and functionality – the options for men’s autumn shoes have never been better. And while it’s great having so much to choose from, it can make settling on the right pair a bit of a challenge.
To help you out, we’ve rounded up some of our favourite styles for this autumn. From retro hiking boots to modern Gore-Tex sneakers, these are the best men’s shoes for autumn as chosen by the OPUMO team.
Lugged deck shoes
Key brand: Timberland
Boat shoes were designed for grip on slippery decks. Unfortunately, that’s where their performance in wet conditions ends. Suffice to say, those thin rubber soles and suede uppers aren’t best suited to the demands of autumn. But if you like the maritime aesthetic, a lugged-sole pair might be the perfect compromise.
Timberland’s lugged deck shoes are the perfect fusion of sea and street, tough enough for a rainy dock but still presentable at the pub. These aren't your summer slip-ons. The lug sole adds that all-important grip and the rugged leather ensures you won't be slipping and sliding in anything but style.
Retro hiking boots
Key brand: Danner
Hiking boots have come a long way in recent years. But as lightweight and breathable as the new breed of boots is, nothing will beat a traditional leather hiker when it comes to stomping through the autumn weather in style.
Danner’s retro hiking boots harken back to a time when people climbed mountains without GPS. Thick leather uppers, Goodyear-welted construction for easy resoling, and bold red laces for a pop of colour. They’re the perfect boots to get you through the Autumn and beyond… even if you're only hiking to the nearest coffee shop.
Commando-sole derbies
Key brand: Kleman
Derbies are perfect for those days when you need to look sharp, but what about when the forecast shows intermittent showers and occasional mud? Our advice would be to ditch the traditional flat soles and go for a grippy commando-sole option instead.
There are loads of brands making chunky Derby shoes, but we’re particularly fond of Kleman’s approach. The best-selling Padror is great if you’re looking for something a bit different. But if you want to keep it classic and understated, check out the Frodan and the Officier instead.
Trail-running shoes
Key brand: Salomon
If you're the sort of person who sees autumn as an opportunity to switch from pavement pounding to woodland trails, Salomon has you covered. The brand's trail-running shoes are designed to tackle rugged terrain, ensuring that even if you're sprinting through mud, your feet will remain dry, comfortable, and well-supported. But you don’t have to be an athlete to reap the benefits.
In case you missed the memo, functional footwear is having something of a fashion moment, which spells excellent news for your autumn footwear options. Take a look at key styles like the Salomon XT-6, XT-4 and ACS Pro to see what all the fuss is about. If you ask us, these truly are some of the best men's shoes for autumn.
Chunky loafers
Key brand: Velasca
Contrary to popular belief, you don't have to consign your loafers to the back of the wardrobe as soon as the first fallen leaf grazes the ground. Yes, these slip-on shoes are most at home in warm weather, but with a few seasonal tweaks they'll gladly carry you through the autumn and beyond.
The most important detail is the sole. Those thin flat outsoles loafers are famous for are, admittedly, not much good on wet ground or in cold weather. Instead, look for loafers that have something a bit beefier, and ideally with a good tread on the bottom too. Just be careful not to stray too far in this direction – part of what makes the loafer such a great style is its low-profile silhouette, so try to find something that strikes a nice balance. Velasca has so great options to get the ball rolling.
Gore-Tex sneakers
Key brand: Hoka One One
For those unwilling to trade style for substance, Hoka’s Gore-Tex sneakers deliver both. These aren’t just any trainers; they’re weatherproof wonders, keeping your feet dry even when your commute gets soggy. You'll stay comfortable, and crucially, your autumn outfits won’t be cheapened by ugly-but-functional footwear.
Gore-Tex works by allowing perspiration vapour to escape from within while blocking water droplets from entering. This makes it perfect for footwear in the colder, wetter months. Keep in mind that only a small selection of the Hoka range is made from this stuff, so always double check the product description carefully before you buy.
Leather Chelsea boots
Key brand: Myrqvist
The Chelsea boot is an autumn classic, and Myrqvist does it justice with a number of sophisticated leather pairs that bridge the gap between smart and casual. Whether you're braving a drizzly commute or enjoying a Sunday stroll through the fallen leaves, these boots will keep you looking sharp without compromising on comfort. The elasticated sides make them easy to slip on when the weather turns nasty—because bending over in the rain is never a good look.
Simple leather sneakers
Key brand: JAK
Minimalism has a home in autumn too. JAK’s simple leather sneakers provide a clean, sleek silhouette that works just as well with tailored trousers as with your favourite jeans. The kind of footwear you can rely on when the weather hasn’t quite made up its mind yet – because why choose between form and function?
The great thing about simple leather sneakers is that they’re surprisingly easy to keep clean. No matter how grim the weather gets, all it takes is a quick wipe down and they’re back to looking brand new.
Cosy house shoes
Key brand: Birkenstock
Sometimes, the best shoe for autumn is the one you never leave the house in. Birkenstock’s house shoes are the ultimate in indoor comfort, perfect for when the temperature drops, and you’ve resigned yourself to the sofa with a cup of something warm.
The German brand’s Boston mules really took off during lockdown and haven’t really gone away since. There are even fleece-lined and wool-felt versions that are perfect for slipping on when it’s cold and wet out.
Leather work boots
Key brand: Red Wing
Autumn has a way of reminding you that there’s work to be done, and Red Wing’s leather work boots are built for the task. Sturdy, durable, and with enough heritage to see you through many seasons to come, they’re the type of boots that look better with age. If you find yourself in need of serious protection—whether it's for work or just navigating the rugged terrain of a weekend walk—these are the boots that won't let you down.
That's the shoes sorted. Why not figure out the rest of your fall wardrobe?
