Lace Up: The Best New Boot Styles For Fall 2025

It’s getting to that time of year again. Leaves are falling, you can see your breath on the morning commute, and low-top footwear is beginning to feel insufficient for day-to-day dealings. This is where a good pair of boots comes in – sturdy, weatherproof and built to march confidently through the colder half of the year while your sandals go into hibernation.

If you’re in the market for a new pair, you may be wondering about the available options. Of course, there are the classics – a nice slim Chelsea boot, a proper pair of Goodyear-welted Derbies – but what if you fancy something a bit different? Well, you’re in the right place.

Below you’ll find a breakdown of some key styles that are peaking in popularity this fall/winter and could be worth investing in. From fashion-forward hiking boots to comfortable moc-toe chukkas, these are the boot styles to know in 2025.

Techy Hikers

Diemme

It’s no secret that outdoor gear has had a stranglehold on menswear for some time now, and yet another symptom is the rise of hiking footwear as everyday wear.

Now, we’re not saying you should start wearing top-of-the-line, purpose-built mountaineering boots with your jeans, but there are several boot brands creating techy, outdoor-inspired footwear with a more fashion-forward angle. Think synthetic materials, vivid pops of colour and leather overlays.

Check out Diemme, Salomon and HOKA, and go from there.

Return Of The Moc

Danner

Classic moc-toe work boots aren’t anything new, but they have been gaining traction again lately.

As workwear staples like raw denim and plaid shirts make a comeback, so too do brands like Danner and Red Wing, which have been crafting the most robust boots in the industry for many decades.

Go for brown leather and a white wedge sole for a classic, versatile look.

Moc-Toe Chukkas

Thursday

Another moc-toe style to consider is the moc-toe chukka. Most people will probably think of a desert boot when they hear the term ‘chukka’, but there are lots of different styles that fit the bill.

As long as it’s mid-height and only features two or three eyelets, you’re on the right track.

Take a look at Clarks’ iconic Wallabee boot for a quick point of reference.

Elevated Desert Boots

Velasca

Clarks is certainly the original when it comes to desert boots. But is it the best? Debatable. Many other brands have since adopted the basic shape and reimagined it in premium materials and high-end construction.

It’s the basic formula, but refined and polished… and with a lofty price tag to match. Check out brands such as Drake’s, Morjas and Tod’s for some of the best pairs around.

Workaday Chelseas

R.M.Williams

Chelsea boots, in general, are quite smart. Sure, you can style them with denim and casual outerwear to dress them down, but they’re most at home with smart-casual outfits and slim tailoring.

However, classic Chelseas aren’t the only option. Down under, there are a number of brands known for making slip-on boots that aren’t shy of a hard day’s work. Boots built for a battering on the building site or at the farm, with sturdy soles and tough uppers that get the job done.

If you’ve got cash to burn, check out R.M. Williams; otherwise, Blundstone is always a safe bet.

Upscale Outdoors

Velasca

Not all outdoor-inspired menswear is brightly coloured and cut from Gore-Tex. There are plenty of more traditional pieces that have been pulled from mountaineering archives and repurposed. And boots are no exception.

From classic gusseted hiking boots like Danner’s Mountain Light to upscale climbing-inspired silhouettes like Paraboot’s Lisse and Yosemite, menswear has plenty of classic outdoor footwear styles to pick from.

And you don’t have to be dressed like Edmund Hillary to pull them off – a pair of selvedge jeans and a heavy flannel shirt will do the trick.

Round-Toe Work Boots

Timberland

We say ‘round-toe work boots’, what we really mean is ‘Timberlands’. The big yellow boots, beloved by builders and rap superstars alike, have been making a big comeback over the last year or two. If you haven’t already dusted yours off, now might be the time to do so.

They’re super durable, comfortable (after the break-in) and are tough enough to take whatever fall and winter can throw their way.

Steer clear of wearing them with tailoring and you can’t go far wrong.

Chunky Derbies

Kleman

Forget slim and streamlined, this season Derby boots mean business. We’re talking chunky lugged soles, premium leather and Goodyear-welted construction.

These are the type of boots that can be dressed down with jeans, but they won’t look out of place paired with a tailored jacket and pants either.

Take a look at what Kleman, Grenson and Dr Martens have to offer.