In autumn and winter, a guy only needs two things to look good: a pair of leather boots, and some quality jeans. Jeans and boots go together so well, and it’s actually quite hard to mess up this look (though not impossible, as we’ll discover below).

If this is your first time ditching the trusty sneakers, there are a lot of variables and combinations to consider. Which jeans should you wear? What style of boots? Can you wear black jeans and brown boots? How do you cuff your pants? What is the difference between Chukkas and desert boots? Can you wear military boots if you’re not in a punk rock band?

In this article we’re going to run through some of the do’s and don’ts of jeans and boots, along with some basics of boot care and maintenance. Let’s crack on.

First things first, you’ll need more than one pair of boots for winter and autumn. This will not only give you more options when it comes to styling, but it’ll prolong the lives of your boots. Even the best quality leather boots need time to rest and recover after each wear, and during winter, moisture and dirt have a habit of getting into the leather, which will eventually dry out and crack your boots without proper care. We generally recommend two or three pairs of boots to get you through the colder seasons. One pair of Chelsea boots, one pair of Chukkas and one pair of military boots is a good place to start.

Jeans and boots are all about balance, and by that we mean matching the correct boot to the correct pair of jeans. Clomping around in thick military boots with painted-on skinny jeans will create a weird, unbalanced look. Likewise hiding your slim Chelsea boots underneath flapping boot-cut jeans. For most of the boots we mention below, a slim-fit pair of jeans works best. For bigger, thicker boots, consider straight cut or regular cut jeans. As long as you stay in that mid-range – not too skinny or too wide – you should be fine.

For 90 per cent of occasions, we recommend cuffing jeans with boots. This will not only look sharper, but it’ll show off more of the boot itself, and help look after the hem of your jeans (ratty, torn hems are definitely not the look we’re going for). We’ve already written a handy cuffing guide over here, if you want to learn the basics. For most boot combinations, we favour a simple double cuff. Just roll your hem once over, and then once over again. The only exception to this is military boots, where you might want to let your jeans ‘stack’ naturally at the top of the boot. For Chukka boots and desert boots, a plain single cuff is totally fine.

Oh, and if you’re considering tucking your boots into your jeans, we’ll save you the trouble. Don’t do it. It never ends well.

_{The Dexter Khaki Chelsea Boots}

This should be your go-to weekend look in winter and autumn; even into spring, if the weather stays cool. What do we mean by casual boots? Simply any boot that isn’t a high-shine, black, chisel-toed Chelsea boot. Save those guys for suits and dark chinos. For casual boots, you want to start with the Chukka and desert boot family (not quite the same thing). These guys are ankle boots with two or three eyelets, rubber or crepe soles, and they come in a variety of colours and textures.

To style Chukka boots with jeans, start with something simple like the BRODY or UTAH, then simply cuff some slim-fit indigo denim and follow up with a crew tee, knit jumper, and a casual jacket. This is also the perfect time to experiment with suede or nubuck boots, like the DAMIEN in tobacco. The soft-touch texture of suede will amp up the casual factor – just be careful to keep it dry and clean.

Jeans and boots are an excellent option for ‘smart casual’ or even ‘semi formal’ events, but they have to be the right jeans with the right boots. For starters, your denim needs to be black or dark indigo. Nothing too light, and certainly nothing textured, ripped or torn. The cut should be fairly conservative, too. That means regular cut or slim-fit – leave the skinny jeans at home. To match these jeans, you need a sharp, slim pair of men’s boots. For formal occasions, we generally recommend Chelsea boots in black or (at a pinch) dark brown. The ARTIE, EASTWOOD and OSBOURNE 2.0 are all solid choices here. A thinner, squarer toe on your boot will look more formal than a wide, rounded one. Just keep that in mind.

Styling formal boors with jeans is fairly straightforward. You want a sharp cuff on your jeans, rather than a stack. Then simply match your boots with a good leather belt, button-up shirt and a knit blazer. Don’t forget a nice dress watch to tie the whole outfit together. If it’s an outdoor event, and you know the weather will be cold, simply layer up with a woollen overcoat or peacoat.

Office dress codes have finally relaxed to the point that, in most offices at least, ‘business casual’ can mean jeans and boots. You can have a little more fun here than you might think. It’s actually a great chance to bust out some suede or nubuck boots, either a desert boot like the DAMIEN or DORADO, or a khaki Chelsea like the DEXTER. The texture of suede can really bring your office attire to life.

_{The Ingram Black Military Boots}

All you have to do is match with some dark indigo jeans (slim-fit or regular cut work best), a leather belt, tonal business shirt (linen is a great option here) and either a textured knit blazer or a sports jacket. Throw in a contrast pocket square for a little extra personality and you’re done! Don’t forget to keep this look tucked and cuffed: that means a sharp double cuff on your jeans and a crisp tuck on your shirt.