The foundations of any good all-purpose autumn/winter outfit are best laid using two key components: some nice sturdy boots, and a quality pair of jeans. Get this right and everything else will fall into place.

It sounds simple enough but for something so basic there are a lot of variables, and by extension, a lot of room for sartorial missteps. Pairing the wrong boots with the wrong jeans has a unique way of making the wearer look comically disproportioned, which we assume is why some men never stray from their trusty sneaker, even in the darkest depths of winter.

You shouldn’t let it put you off though, because armed with a bit of know-how and a few go-to combinations there’s no reason anyone can’t pull off boots with jeans. Here we explore the tricks of the trade along with a few fail-safe outfit ideas to get the ball rolling.

Wearing Boots With Jeans: The Fundamentals

Strike A Balance

Ensuring everything is in proportion is pivotal to making your boots and jeans work together. A pair of low-profile Chelsea boots with wide-leg denim, for example, is never going to work well. Conversely, big clumpy winter boots and drainpipes isn’t a good idea either.

Instead, always make sure the fit of your jeans complements the style of your boots and vice versa. A slim leg is usually a safe bet, but for some chunkier boot shapes, you may want to consider a straight or relaxed fit. As a rule of thumb, if your jeans don’t comfortably fit over the top of your boots then you shouldn’t wear them.

Cuff Or Bust

Allowing the uncuffed hem of your jeans to drape clumsily over the top of your boot is all well and good if you’re Jeremy Clarkson. But everyone else should add a few turn-ups into the mix.

Cuffing is the secret of wearing boots with jeans and making it look good. It breaks up the line of the leg a little and creates a clear point at which your legwear ends and footwear begins. One thing to remember, though, is that bigger cuffs can make your lower half appear shorter, so if you’re below average height then stick to smaller turn-ups.

Consider Colour

As far as colour combinations go in the world of boots and jeans, there’s very little that’s off limits. However, in order to really make an outfit sing, it’s worth knowing that certain shades go together better than others.

As a general rule, avoid anything that matches too closely, unless it’s black on black. Broadly speaking, it’s also better to pair lighter denim with lighter-coloured boots. For example, stonewash jeans and dark-brown footwear can jar. When it comes to dark or raw denim, pretty much anything goes.

To Tuck Or Not To Tuck?

The question of whether to tuck pants into boots or not is one that has plagued men since they first began wearing the two things together. Allow us to clear things up once and for all: don’t do it.

Unless you’re an on-duty member of the armed forces, or in an early 2000s manufactured boy band, your legwear should never see the inside of your boots. Again, cuff them at the hem and wear them over the top. In an ideal world, they should break somewhere around, or just above, the ankle.

Five Ways To Wear Boots With Jeans

All Black Everything

An all-black outfit with black leather boots may conjure up images of The Cure and Edward Scissorhands but bear with us. There are, in fact, ways to pull this particular look off without looking like something that leapt out of Tim Burton’s imagination.

In fact, there are a lot of ways to do it. All black with boots and jeans is highly versatile and can be bent to suit most social settings.

For a bit of rock ‘n’ roll swagger, try incorporating a leather biker jacket and black leather Chelsea boots. Layer with knitwear on colder days and make sure everything fits nice and trim. If leather’s not to your taste, why not try going with a simple black overshirt and T-shirt combination for something more laid back?

Business Casual

Office dress codes have been relaxing for a long time now, and unless you’re one of the unlucky few whose corporate employer requires they be forced into a suit every day of the week, boots and jeans can provide an excellent 9-5 option for your lower half.

Hitting the sweet spot between business and casual is key here, so it’s always a good idea to incorporate some sort of sports jacket. A classic blazer looks sharper, but something unstructured and a little more relaxed can look good, too.

Boots-wise, stick to Chelseas or Derbies. And as for the denim, the darker it is, the smarter it looks.

Keep It Simple

It’s often the case in menswear that less equals more, and styling boots and jeans is no exception. Keeping things simple is a good way to make outfits infinitely more versatile, low maintenance and foolproof to pull off, so ditch the unnecessary and take things back to basics.

Quality plain T-shirts, crew neck sweaters, Oxford shirts, denim and boots are all undisputed wardrobe heroes. They’re fuss-free, unassuming and work well on their own, but they’re also hard to beat when worn together.

Forgo logos, heavy branding and accessories and instead keep things clean and uncluttered. Black leather or suede Chelsea boots are a nice minimalist option but don’t be afraid to try different styles and colours, too. A beige suede desert boot, for example, is a classic design that’ll work with anything.

White Jeans

It’s easy to write white denim off as something that only reality TV contestants wear, but style it right and it can be a valuable tool.

Teaming dark boots with white jeans is one of the only instances in which the “lighter jeans = lighter boots” rule doesn’t stand up. In this case, it’s a great way of creating contrast within an outfit and can look pretty sharp when executed correctly.

Contrast is the operative word here, so you’ll want to make sure your boots and your upper half are dark to keep things balanced. Think overshirt and roll neck for smart-casual events, or a tucked T-shirt and bomber jacket for something more relaxed. Whichever way you go, just be sure to steer clear of red wine and dirty chairs.

Weekend Casual

Unwinding at the weekend is where boots and jeans are at their best. Whether you’re kicking up leaves on a Sunday afternoon stroll in the park or heading to the bar to meet friends, the right denim paired with the right boots won’t let you down.

A simple T-shirt or polo shirt with slim-fit denim and casual boots, topped off with a lightweight jacket is a go-to weekend look that can be thrown on without a second’s thought. It’s easy, stylish and versatile enough to see you through most social situations you’re likely to find yourself in on a Saturday or Sunday.