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Boots With Jeans: How To Get This Classic Combination Right

The most stylish ways to wear boots with jeans that won't have you looking like you're in an early 2000s boy band.

Words by: Charlie Thomas

Cowboys, bikers and punks all did it. Hell, even style bloggers of the early noughties were onto something… All were champions of a can’t-fail menswear combination: wearing boots with jeans. They did often and they did it well.

Depending on how you style it, boots and jeans channel an attitude of subtle rebellion, rock ‘n’ roll dandy or rugged Americana. Whichever way you lean, this pairing injects an instant dose of throwback cool into your wardrobe.

But what boots should you go for? And what cut of jeans work best? From styling advice to boots with jeans outfit inspiration, here’s the lowdown on this classic combo.

Boots with jeans: why it works

Men's work boots worn with turned up selvedge denim jeans

Taylor Stitch

Why wouldn’t it? Wearing boots with jeans is easy, considered and masculine as hell. Whether you go for a Chelsea boot and black jeans or a worn-in brown Derby boot and raw denim pairing, you’ll look laid back and stylish every time.

There’s a reason why the world’s best-dressed men have turned to this combination for decades. From Marlon Brando and James Dean to Ryan Gosling and David Beckham, menswear icons have, time and again, made boots and jeans a key part of their look.

If you’re not sure what to wear for an evening out or a weekend about town, try a simple T-shirt, jeans and boots outfit, and don’t give it a second thought. Honestly, you can’t go wrong.

When to wear ankle boots with jeans

Men's boots with jeans smart casual winter outfit

Private White V.C.

For relaxed, off-duty style, boots and jeans are damn near perfect. Think weekend walks with family, after work drinks with colleagues and friends, or dates at a restaurant or museum – boots with jeans are easy going and suitable for a range of situations.

They also offer a considered look, and one that’s a degree sharper than jeans with sneakers. Depending on the exact combo you go for, boots and jeans can also be smart-ish, especially when dressed up with sharp shirts, unstructured tailoring and, in winter, long overcoats.

It’s a more versatile pairing than you might first think and one you’ll come back to often.

The best boots to wear with jeans

There are, of course, some boots that work better with jeans than others. Jeans are an inherently casual item, so it’s best to match their laid-back nature for seamless results. That means anything too formal like Oxford boots are out of the picture.

Everything else is pretty much fair game, depending on what exactly you’re going for. That means Derby boots, brogue boots, Chelsea boots and desert/chukka boots all work well with jeans, although each style has its own merits.

Derby and desert boots are perhaps the most versatile option, working with a wide range of denim from regular tapered designs to black slim fits. Brogue boots and leather chukkas are slightly smarter, and look best in dark brown teamed with indigo denim.

Chelsea boots are the ideal in-between silhouette, offering equal levels of sophistication and relaxed elegance. Black Chelseas with black denim creates a timeless, rock ‘n’ roll-inspired aesthetic, while dark brown, chunky-soled versions work especially well with blue jeans.

The best jeans to wear with boots

Men's slim blue jeans worn with suede Chelsea boots

34 Heritage

While the boots might be the most important aspect of this particular pairing, it’s important not to overlook the denim above them. The wrong jeans can ruin a perfectly acceptable pair of boots, so nailing the fabric, fit and colour is important.

Again, the style you choose depends on the kind of look you’re after. Want to channel a classic, mid-century, James Dean-inspired feel? You’ll want a regular cut pair of dark- or mid-wash denim jeans. Going for something more rock-inspired that incorporates Chelsea boots? Slim, dark denim it is.

Regardless of what look you’re going for, the hems of your jeans need considering. Look for a pair which tapers to the ankle, so the hem isn’t bagging around the top of the boot. But don’t go so narrow that they’re skin-tight either. The hems should fit over the ankle of the boots, giving your jeans a clean, unbroken line, which is both flattering and still shows off your footwear choice.

Ankle boots with jeans outfits

Matching browns

Men's mid wash jeans with Dr Martens brown leather boots, grey hoodie an d


One effective way of wearing boots with jeans is to go tonal. This can be done with the entire outfit, or with select pieces, like a jacket or shirt. Try the former and combine a light brown pair of boots with a complementary light brown jacket, and finish with a grey hoodie and mid-wash denim jeans.

Slim black jeans

Men's black jeans and green padded overshirt outfit

Selected Homme

For a classic casual look, combine a pair of slim black jeans with black boots. Look for jeans with a taper down to the ankle, which should sit just on the top of the boots for a clean, unbroken trouser line. Finish the look with a simple black tee and add a bit of contrast with a green coach jacket.

Blue and brown

Men's workwear outfit with black jeans, brown overshirt and chelsea boots

Selected Homme

Arguably the easiest way to wear boots with jeans is by opting for classic tones that never fail to work together. A pair of dark blue denim jeans worn with dark brown leather boots is a timeless combination and one that channels an effortless workwear feel.

Go casual on the top half with a grey sweatshirt or embrace the utilitarian vibe with a western shirt and simple black tee.

Dressed down monotone

Men's grey jeans, black Chelsea boots and black hoodie outfit


An easy rule for dressing in general, but one that works especially well with boots and jeans is going monotone. A simple look consisting of dark grey jeans, black Chelsea boots and a black hoodie is one you can wear on long walks and to noisy gigs alike.

Weekend staple

Men's white tee and checked overshirt worn with jeans and boots


For three months of the year, boots might be the only shoes you need. Find a solid pair of chunky-soled Derbies or Chelseas and you can wear them with everything from tailored trousers and jackets to jeans and overshirts.

Opt for the latter and you’ve got a staple weekend look that’s easy to throw on and go.

Contrasting leathers

Men's black jeans and brown leather motorcycle jacket outfit


If you have a passing interest in menswear you might have heard the rule that you should always match your leathers. Well, rules are made to be broken. The trick in pulling it off is to opt for contrasting colours; take a light or mid-brown leather jacket and combine it with black leather boots and the move will look deliberate.

Denim and Chelsea boots

Men's stonewash blue jeans with brown boots, roll neck, blazer and shearling jacket outfit

Brunello Cucinelli

Black denim is a natural pairing for black Chelsea boots, but for something less severe yet equally sharp, try mid-blue jeans work with brown leather boots.

Keep the fit of the jeans relaxed and ensure they’re slightly cropped in order for them to sit perfectly over the top of the boots. If not, don’t be afraid to roll the hem to avoid any excess fabric bunching up at the bottom.

Mid-century leather

Men's black jeans, black boots, white T-shirt and black leather jacket outfit

Buck Mason

The likes of James Dean and Marlon Brando were often seen in boot and jeans, both on and off screen, in the 50s and the mid-century look is one that simply doesn’t age.

To channel these icons today, go for a pair of slim-fitting black jeans and team them with tonal black leather boots, a black leather jacket and crisp white tee.

Chunky boots

Men's twill shirts, blue jeans and chunky brogue boots outfit

Buck Mason

Thick, rubber-soled boots are on trend and arguably the most versatile option you can buy in 2024. Go for dark brown or black Derby boots replete with a durable rubber sole, which not only looks great but is able to withstand a lot more abuse than their leather-sole counterparts.

When it comes to styling combine them with equally rugged pieces such as twill or flannel shirts, chore coats and selvedge denim.

Black and white

Men's white jeans, white denim jacket, black shirt and black boots outfit


All-white outfits are notoriously hard to pull off (and besides, white boots are best saved for astronauts and rodeo riders). Much better to break up the look with other complementary shades.

Black might not be your first choice for summer, but the contrast with white works particularly well if it’s done in a subtle way. For example, try a black pair of Chelsea boots with white jeans, an off-white jacket and a black shirt to tie the look together.

Country wear

Men's country outfit with selvedge denim, brown boots, ribbed sweater and camel overcoat

Private White V.C.

Boots are a natural fit for a look consisting of classic British country staples. Think long, warm wool coats, soft scarves, ribbed knitwear and selvedge denim jeans. Look for a pair of brogue or chunky-soled Derby boots in brown leather, and combine them with all of the above for weekend walks in town or country.

Suede it up

Men's grey jeans with brown suede boots, jacket and white Henley shirt outfit

Ralph Lauren

Suede isn’t the easiest of materials to wear. But combine it with denim jeans and, as long as the fit is on point, you can’t miss. For a classic menswear combo, try a mid-brown suede jacket with stonewashed denim for some 70s flavour, using complementary dark brown suede boots to complete the look.

Brown on brown

Men's raw denim jeans worn with brown boots, lightweight sweater and brown overcoat outfit


Brown works well with navy, but it works even better when combined with other, earthy shades. For a versatile fall outfit, try a brown overcoat worn over a light brown gilet and stone knit, accessorising with a brown patchwork scarf.

Complete the look with dark denim and versatile brown leather Derby boots, which will only get better with age.

Roll those hems

Men's selvedge jeans, black boots, ribbed sweater and black peacoat outfit


When it comes to jeans, you don’t want a pair that’s too long, spilling over the tops of your boots. Instead, try turning up the hems to reveal the lighter blue tone on the fabric’s reverse, which looks great and allows you to show off a pair of high-ankle leather boots.

Keep it simple

Men's raw denim jeans, brown work boots and beige T-shirt outfit

Taylor Stitch

One of the most effective ways of wearing boots with jeans is by keeping it simple. For a timeless spring look, try a regular tapered pair of denim jeans with light brown moccasin boots and a crisp T-shirt. It’s cool, classic and channels a slice of throwback Americana.

Menswear staples

Men's white jeans and green bomber jacket outfit with suede desert boots

Todd Snyder

The desert boot is an underrated design but a verified wardrobe essential. Easy to dress up with an unstructured suit, or down with jeans and a tee, these are soft, comfortable boots that work in any situation.

Opt for smart casual ground and try yours with off-white jeans, a grey T-shirt and a Harrington jacket for a contemporary take on classic mod style.

All black

Men's smart all black outfit of turtleneck, jeans and overcoat with Chelsea boots


All black will always look cool. Easy to throw on and slimming for the wearer, all-black outfits let you (almost literally) get dressed in the dark. Try it for yourself with black derby boots, slim black jeans and a matching roll neck for a dash of 60s-inspired Parisian cool.

Finish with a black wool overcoat and you’ll look great whether you’re heading to the theatre, a first date or a clandestine meeting with a double agent.