Men’s boots are all about versatility. Depending on the style, and the material, you can find boots for hot summer picnics, blustery autumn afternoons and long slogs through freezing winter rain. And with proper care, a good pair of leather boots can last season after season, long after your thongs have snapped (always in a beach carpark, for some reason, and always on days when the concrete could fry an egg).
The trick is picking the right boot for the right season, and having a couple of pairs that will keep your feet comfy year-round. But don’t hold too fast to traditional rules. Chukka boots with shorts are definitely a thing, and you can even wear military boots in summer (more on this down below).
Consider this your seasonal men’s boot crash course.
Men’s boots for summer
Obviously men’s boots won’t be suitable for every summer day. That’s why god invented moccasins. But for sunny afternoons in the park or drinking Sav Blanc at some fancy country vineyard, you can’t beat a lightweight pair of boots.
For summer boots, we recommend anything ankle-height, which generally means Chukka boots and Desert boots (not quite the same thing). Chukkas and Desert boots are lightweight, extremely comfortable and always on-trend. Styling them is simple, too. Some high-cuffed chinos, Desert boots and a crew tee is a no-fuss summer look, but you can also pair suede Chukkas with chino shorts (try and match the tone, if possible). Desert boots with shorts and a lightweight, long sleeve knit is also an option, if the weather’s not too hot. The general rule with summer ankle boots is: no visible socks. Use ankle socks or invisible socks instead. You don’t want to see anything peeking over the boot.
Summer is also a great season to experiment with materials. Because you’re less likely to get wet, consider picking up a pair of suede or nubuck boots, like the DORADO. Throw on some cuffed tan chinos and a linen shirt and you’re ready for that summer barbecue. Just keep in mind, if you’re going down the suede or nubuck route, you’ll need to pick up some dedicated suede shampoo.
Men’s boots for autumn
Autumn is a bit of a mixed bag, weather-wise, so you need to be prepared for anything.
Again, a lightweight pair of Chukkas is a good option here—maybe the full-leather OLDMAN, for added weather resistance. You can match these guys with double-cuffed indigo denim, then layer up with a crew knit and khaki anorak. For dressier occasions, pick up a pair of leather ankle boots like the UTAH or ADAMS. These always look sharp under some slim-fit dark jeans and a contrast knit blazer. Just remember to match your leather accessories: brown boots go with a brown belt, and vice versa for black.
The other option for autumn is, of course, the ever-reliable Chelsea boot. We’ve written an entire guide on Chelsea boots, but the short version is this: they go with everything. If we could recommend one men’s boot that will see you through every season, it’d be a leather Chelsea like the OSBOURNE 2.0 or the HARLEY. These guys look good under chinos, jeans or even shorts. If you’re going down the shorts route, lean into the counter-culture vibes: that means Chelsea boots, retro mid-calf socks, chinos shorts and a loose-fitting tee. Throw on some sunnies, too. It’s a risky play, but it can work on warmer autumn days.
Men’s boots for winter
Winter is when you need to be really thinking about boot materials and boot care. All that rain, all that added moisture and mud, that’s the stuff that ruins men’s leather boots. The water tends to get between the vamp (the boots’ upper) and the welt (the bit where the upper joins the sole). The leather expands, contracts, dries out and cracks, forcing the boots apart.
So first things first: no suede or nubuck. Not in winter. You want hard-wearing full leather uppers and leather lining—for warmth as well as waterproofing. A good shoe spray can also work wonders. During winter, we recommend something higher and heavier, like our rubber-soled military boots. This is often the only season when you can bust out a chunky combat boot, so go nuts.
To style military boots, you need to think in terms of weight. Heavy boots on your ankles need to be balanced with heavy layers on top. Generally this isn’t a problem in winter, since you’ll be wanting lots of layers anyway. Try thick brown military boots, like the MASSIMO, or sleek black boots, like the INGRAM. Pair them with cuffed denim (you want a nice, high cuff for combat boots), a textured knit and a heavy woolen overcoat. Bonus points for scarves, beanies and extra layers. For more information, we’ve written a comprehensive winter boot guide over here.
Men’s boots for spring
Spring is a little like autumn: you need to keep one eye on the weather forecast at all times. There’s nothing worse than walking out in your new khaki suede DAYTON boots and then running for cover when it rains.
Something like a low-rise, round-toed LUCCA Chelsea boot is great for spring: it’s comfortable enough to walk around all day, and the rubber sole and leather upper can handle any unexpected showers. Our leather OLDMAN Chukka boots are equally versatile. You can dress these down with basic chinos and a crew-neck tee, or even pair them with chino shorts and a linen shirt. Boots in spring need to handle pretty much anything the sky throws at them, so think lightweight, comfortable and waterproof.
Special shout out to military boots with shorts here. It’s a bold combination, but it can definitely work in spring (and you’ll be laughing if the weather turns sour). To pull off this look, match your leather military boots with some neutral shorts, thick socks (you actually want to show some sock here), a loose V-neck tee and an oversized anorak. The loose, baggy layers on top help balance the thicker boots, and something like the WHEELER or INGRAM is perfect for this look. Definitely high stakes, but high reward.