A Modern Man’s Guide To Wearing Cowboy Boots

Do you enjoy the Western aesthetic but don't know how to incorporate it into your daily style? Here are a few ideas for what you can wear with a pair of cowboy boots to nail the modern man's country look.

Cowboy Boots With A T-Shirt & Jeans

The easiest way to style cowboy boots in a casual outfit is to pair them with a t-shirt and denim. This combo looks effortless yet still makes you stand out in a good way.

Men's Brown Suede Cowboy Boots, Light Blue Jeans, White Crew-neck T-shirt
The go-to for a kick-ass relaxed look for men? A white crew-neck t-shirt with light blue jeans. You could perhaps get a bit experimental when it comes to shoes and introduce brown suede cowboy boots to the equation.View Details
Men's Brown Leather Cowboy Boots, Charcoal Jeans, White Crew-neck T-shirt
A white crew-neck t-shirt and charcoal jeans are absolute menswear essentials that will integrate well within your day-to-day arsenal. And if you want to effortlesslly tone down your ensemble with shoes, why not complete your ensemble with brown leather cowboy boots?View Details
Men's Tan Suede Cowboy Boots, Navy Jeans, White Crew-neck T-shirt
If you wish take your off-duty fashion game to a new level, try teaming a white crew-neck t-shirt with navy jeans. Bring a bit more edginess to by slipping into a pair of tan suede cowboy boots.View Details
Men's Black Beanie, Brown Suede Cowboy Boots, Charcoal Jeans, Navy Crew-neck T-shirt
One of the coolest ways for a man to style a navy crew-neck t-shirt is to pair it with charcoal jeans in a casual combination. Want to break out of the mold? Then why not complete this outfit with brown suede cowboy boots?View Details
Men's Burgundy Leather Cowboy Boots, Blue Jeans, White and Black Print Long Sleeve T-Shirt
This casual street style combination of a white and black print long sleeve t-shirt and blue jeans is super easy to put together in next to no time, helping you look amazing and ready for anything without spending too much time rummaging through your wardrobe. And if you want to immediately tone down your look with a pair of shoes, why not complement your look with burgundy leather cowboy boots?View Details
Men's Dark Brown Beanie, Tan Suede Cowboy Boots, Navy Jeans, Dark Brown Crew-neck T-shirt
This casual combination of a dark brown crew-neck t-shirt and navy jeans is extremely easy to throw together in seconds time, helping you look stylish and ready for anything without spending a ton of time going through your wardrobe. Finish off with a pair of tan suede cowboy boots to transform this ensemble.View Details
Men's Navy and White Print Baseball Cap, Burgundy Leather Cowboy Boots, Navy Jeans, Navy Print Crew-neck T-shirt
Choose a navy print crew-neck t-shirt and navy jeans for an off-duty ensemble with a city style spin. For a truly modern on and off-duty mix, add burgundy leather cowboy boots to the mix.View Details

Cowboy Boots With A Plaid Shirt

Plaid check is another common element of the country look. So a plaid shirt looks quite in sync with a pair of cowboy boots. For a more modern and more laid-back take though, throw on a plaid shirt jacket or a flannel shirt over your tee, jeans and cowboy boots combo.

Men's Brown Leather Cowboy Boots, Black Jeans, Grey Crew-neck T-shirt, Orange Plaid Shirt Jacket
You'll be surprised at how very easy it is for any gent to get dressed this way. Just an orange plaid shirt jacket worn with black jeans. A pair of brown leather cowboy boots will add a carefree touch to this ensemble.View Details
Men's Brown Leather Cowboy Boots, Blue Jeans, White Tank, Multi colored Plaid Long Sleeve Shirt
This combination of a multi colored plaid long sleeve shirt and blue jeans is hard proof that a safe casual look doesn't have to be boring. Dial up your whole look by finishing off with brown leather cowboy boots.View Details
Men's Black Leather Cowboy Boots, Black Chinos, White and Black Plaid Dress Shirt, Tobacco Suede Shirt Jacket
A tobacco suede shirt jacket and black chinos are a combination that every modern gentleman should have in his wardrobe. Finishing off with a pair of black leather cowboy boots is a surefire way to infuse a more relaxed vibe into your ensemble.View Details
Men's Tan Suede Cowboy Boots, Khaki Jeans, White Check Long Sleeve Shirt, Black Leather Biker Jacket
For relaxed dressing with a modern twist, you can easily wear a black leather biker jacket and khaki jeans. Tone down your look by sporting tan suede cowboy boots.View Details

Cowboy Boots With A Denim Shirt

Another good way to wear cowboy boots for casual Americana vibes is to pair them with a denim shirt or jacket. If you want to go full prairie in double denim, opt for the top and bottom in different colors.

Men's Burgundy Leather Cowboy Boots, Navy Jeans, Navy Denim Shirt, Charcoal Overcoat
This combo of a charcoal overcoat and navy jeans looks amazing, but it's also super easy to throw together. On the shoe front, go for something on the casual end of the spectrum with burgundy leather cowboy boots.View Details
Men's Brown Leather Belt, Brown Leather Cowboy Boots, Black Jeans, Light Blue Chambray Long Sleeve Shirt
If you like the comfort look, team a light blue chambray long sleeve shirt with black jeans. Spice up this ensemble with more laid-back shoes, such as these brown leather cowboy boots.View Details
Men's Black Jeans, Beige Long Sleeve T-Shirt, Blue Denim Shirt, Tan Barn Jacket
For something more on the cool and laid-back end, try teaming a tan barn jacket with black jeans. If you want to instantly play down this look with footwear, why not introduce brown leather cowboy boots to the equation?View Details
Men's Tobacco Chinos, Olive Plaid Long Sleeve Shirt, White Fair Isle Zip Sweater, Light Blue Denim Jacket
This combo of a light blue denim jacket and tobacco chinos is proof that a pared down off-duty outfit doesn't have to be boring. Our favorite of a great number of ways to complement this outfit is black leather cowboy boots.View Details
Men's Tobacco Leather Cowboy Boots, Dark Brown Corduroy Jeans, Purple Plaid Long Sleeve Shirt, Navy Denim Jacket
This combo of a navy denim jacket and dark brown corduroy jeans is hard proof that a safe off-duty outfit doesn't have to be boring. Feeling brave today? Switch up your getup by finishing off with tobacco leather cowboy boots.View Details
Men's Brown Leather Cowboy Boots, Beige Jeans, White Long Sleeve Shirt, Navy Denim Jacket
Consider wearing a navy denim jacket and beige jeans for a casual and stylish look. A great pair of brown leather cowboy boots is the simplest way to add a dash of stylish casualness to this getup.View Details
Men's Tan Suede Cowboy Boots, Khaki Jeans, Light Blue Chambray Long Sleeve Shirt, Navy Denim Jacket
A navy denim jacket and khaki jeans are a good combination worth having in your day-to-day wardrobe. To give your outfit a more laid-back spin, why not add a pair of tan suede cowboy boots to the mix?View Details
Men's Brown Suede Cowboy Boots, Light Blue Jeans, Grey Horizontal Striped Crew-neck T-shirt, Black Denim Jacket
For a casual getup, reach for a black denim jacket and light blue jeans — these items fit beautifully together. To give your overall ensemble a more casual vibe, add brown suede cowboy boots to this getup.View Details

Cowboy Boots With Skinny Jeans

Younger guys’ approach to cowboy boots is to pair them with skinny-fit jeans. Take cues, for instance, from Harry Styles’ combinations of Saint Laurent cowboy boots and skinny jeans.

Harry Styles wearing Brown Suede Cowboy Boots, Black Skinny Jeans, Grey Crew-neck T-shirt, Beige Fleece Gilet
A beige fleece gilet and black skinny jeans are among the key pieces in any modern man's properly edited casual collection. Introduce a pair of brown suede cowboy boots to your look to avoid looking too formal.View Details
Harry Styles wearing Black Sunglasses, Grey Leather Chelsea Boots, Black Skinny Jeans, Black Crew-neck T-shirt
This city casual combo of a black crew-neck t-shirt and black skinny jeans can only be described as ridiculously stylish. Rounding off with grey leather chelsea boots is a guaranteed way to introduce a bit of fanciness to this outfit.View Details
Harry Styles wearing Tan Suede Chelsea Boots, Black Wool Dress Pants, Black Print Crew-neck Sweater, Tan Shearling Coat
We love the way this pairing of a tan shearling coat and black wool dress pants instantly makes any gent look stylish and elegant. A pair of tan suede chelsea boots will be a stylish accompaniment for this outfit.View Details
Harry Styles wearing Tan Suede Chelsea Boots, Black Skinny Jeans, Grey Hoodie, Tan Shearling Coat
Marry a tan shearling coat with black skinny jeans for a fuss-free look that's also pulled together nicely. Not sure how to round off this ensemble? Wear tan suede chelsea boots to amp it up a notch.View Details
Men's Black Leather Belt, Brown Suede Cowboy Boots, Black Ripped Skinny Jeans, White Silk Long Sleeve Shirt
Wear a white silk long sleeve shirt with black ripped skinny jeans to be both laid-back and comfortable. This outfit is rounded off nicely with brown suede cowboy boots.View Details
Men's Tan Suede Cowboy Boots, Blue Jeans, Black Fair Isle Crew-neck Sweater
For an on-trend look without the need to sacrifice on comfort, we love this combination of a black fair isle crew-neck sweater and blue jeans. To introduce a mellow vibe to this look, complement this ensemble with a pair of tan suede cowboy boots.View Details
Men's Black Suede Cowboy Boots, Black Skinny Jeans, Red and Black Check Flannel Long Sleeve Shirt, Black Suede Biker Jacket
Consider wearing a black suede biker jacket and black skinny jeans for both stylish and easy-to-wear outfit. Kick up the wow factor of your ensemble by sporting black suede cowboy boots.View Details
Men's Black Leather Cowboy Boots, Black Skinny Jeans, Black Crew-neck T-shirt, Black Leather Biker Jacket
A black leather biker jacket and black skinny jeans are a great combination to have in your daily styling repertoire. Bring a more casual twist to by finishing off with black leather cowboy boots.View Details
Men's Tobacco Suede Cowboy Boots, Black Skinny Jeans, White and Black Horizontal Striped Crew-neck T-shirt, Brown Suede Harrington Jacket
Definitive proof that a brown suede harrington jacket and black skinny jeans are amazing when worn together in a casual outfit. Puzzled as to how to finish? Add tobacco suede cowboy boots to the mix for a more laid-back aesthetic.View Details
Men's Tan Suede Chelsea Boots, Black Skinny Jeans, White Crew-neck T-shirt, White and Navy Plaid Long Sleeve Shirt
This combo of a white and navy plaid long sleeve shirt and black skinny jeans is the perfect foundation for a casually cool getup. Introduce tan suede chelsea boots to your look to easily kick up the classy factor of any outfit.View Details
Men's Black Leather Cowboy Boots, Black Leather Jeans, Black Long Sleeve Shirt, Black and Gold Blazer
A black and gold blazer and black leather jeans are powerful players in any man's wardrobe. For a truly modern hi/low mix, complement this look with black leather cowboy boots.View Details

Cowboy Boots With A Blazer Or A Suit

You can recreate one of the signature cowboy looks by wearing your Western boots with a button-up shirt, a pair of jeans and a blazer jacket. Want to dress it all the way up? Try pairing cowboy-inspired ankle boots with a suit.

Men's Beige Suede Desert Boots, Blue Jeans, Light Blue Dress Shirt, Grey Wool Blazer
Putting together a grey wool blazer and blue jeans is a guaranteed way to infuse your day-to-day styling lineup with some casual refinement. On the footwear front, this look pairs perfectly with beige suede desert boots.View Details
Men's Grey Leather Cowboy Boots, Navy Jeans, Grey Long Sleeve Shirt, Black Blazer
For an effortlessly refined getup, consider pairing a black blazer with navy jeans — these two pieces go beautifully together. Give a laid-back touch to this outfit with grey leather cowboy boots.View Details
Men's Dark Brown Leather Cowboy Boots, Light Blue Jeans, Tan Turtleneck, Dark Brown Herringbone Blazer
Putting together a dark brown herringbone blazer and light blue jeans will allow you to show off your prowess in menswear styling even on off-duty days. Dark brown leather cowboy boots can immediately dress down an all-too-dressy look.View Details
Men's Brown Leather Cowboy Boots, Navy Jeans, Light Blue Horizontal Striped Long Sleeve Shirt, Navy Houndstooth Blazer
A navy houndstooth blazer and navy jeans? This is an easy-to-wear ensemble that you could wear on a day-to-day basis. Finish with brown leather cowboy boots to upgrade your look.View Details
Men's Black Leather Cowboy Boots, White Turtleneck, Grey Suit
This combination of a grey suit and a white turtleneck can only be described as seriously dapper and elegant. Black leather cowboy boots are guaranteed to give a dash of stylish effortlessness to your outfit.View Details
Men's Black Leather Cowboy Boots, Yellow Wool Dress Pants, Black and White Print Short Sleeve Shirt, Red Check Blazer
Consider pairing a red check blazer with yellow wool dress pants if you're aiming for a proper, stylish ensemble. Dial down the formality of your look by rounding off with black leather cowboy boots.View Details
Men's Burgundy Leather Cowboy Boots, White Dress Shirt, Charcoal Suit
To look like a true gentleman, choose a charcoal suit and a white dress shirt. If you need to easily play down your outfit with one single piece, complement this outfit with a pair of burgundy leather cowboy boots.View Details
Men's Tan Suede Cowboy Boots, Black Dress Pants, Black Crew-neck T-shirt, Black Overcoat
One of the most elegant ways to style out such a hard-working menswear item as a black overcoat is to wear it with black dress pants. Ramp up the cool of this look by finishing off with tan suede cowboy boots.View Details
Men's White Crew-neck T-shirt, Grey Vertical Striped Suit, Tobacco Suede Shirt Jacket, Olive Overcoat
Putting together an olive overcoat and a tobacco suede shirt jacket will create a sophisticated, rugged silhouette. Brown suede cowboy boots are an effortless way to upgrade this ensemble.View Details

More Outfits With Cowboy Boots

Men's Brown Leather Cowboy Boots, Black Jeans, Black Crew-neck T-shirt, Tan Barn Jacket
For a look that offers functionality and fashion, dress in a tan barn jacket and black jeans. You can get a little creative on the shoe front and dress down your look by sporting brown leather cowboy boots.View Details
Men's Black Leather Cowboy Boots, Grey Jeans, Black Chambray Long Sleeve Shirt, Black Corduroy Shirt Jacket
The pairing of a black corduroy shirt jacket and grey jeans makes this a knockout casual getup. A cool pair of black leather cowboy boots is the most effective way to transform this look.View Details
Men's Brown Leather Belt, Dark Brown Leather Cowboy Boots, Navy Jeans, Brown Fair Isle Shawl-Neck Sweater
The formula for killer relaxed casual style for men? A brown fair isle shawl-neck sweater with navy jeans. If you don't want to go all out formal, add dark brown leather cowboy boots to your look.View Details
Men's Tan Suede Cowboy Boots, Beige Jeans, White Long Sleeve Shirt, Brown Denim Jacket
Reach for a brown denim jacket and beige jeans to feel fully confident in yourself and look trendy. On the shoe front, go for something on the casual end of the spectrum and complement your look with tan suede cowboy boots.View Details
Men's Brown Leather Cowboy Boots, Navy Jeans, White Crew-neck T-shirt, Navy Print Crew-neck Sweater
This combination of a navy print crew-neck sweater and navy jeans will hallmark your prowess in men's fashion even on lazy days. A pair of brown leather cowboy boots will bring a laid-back aesthetic to the outfit.View Details
Men's Tan Suede Cowboy Boots, Navy Jeans, Black Paisley Long Sleeve Shirt, Grey Overcoat
Putting together a grey overcoat and navy jeans is a fail-safe way to infuse a classy touch into your wardrobe. Complement this getup with tan suede cowboy boots to immediately up the appeal of your ensemble.View Details
Men's Tan Snake Leather Chelsea Boots, Black Jeans, Black and White Print Short Sleeve Shirt, Tan Suede Biker Jacket
Extremely stylish, this relaxed combination of a tan suede biker jacket and black jeans will provide you with amazing styling opportunities. If you wish to easily polish up your outfit with one piece, why not complete your look with a pair of tan snake leather chelsea boots?View Details
Men's Dark Brown Leather Cowboy Boots, Black Jeans, White and Navy Vertical Striped Long Sleeve Shirt, Navy Shirt Jacket
A navy shirt jacket and black jeans are the kind of a tested casual combo that you need when you have zero time to dress up. Round off with dark brown leather cowboy boots to effortlesslly up the appeal of your getup.View Details
Men's Brown Suede Cowboy Boots, Black Jeans, Black Crew-neck T-shirt, Black Zip Sweater
When the situation permits a casual look, go for a black zip sweater and black jeans. Add brown suede cowboy boots to your look to immediately turn up the cool of this look.View Details
Men's Black Suede Cowboy Boots, Black Jeans, White Dress Shirt, Black Leather Bomber Jacket
Go for a black leather bomber jacket and black jeans to create a neat and relaxed look. For a more relaxed aesthetic, why not complement your look with a pair of black suede cowboy boots?View Details
Men's Brown Suede Cowboy Boots, Brown Dress Pants, Navy Geometric Overcoat
For an ensemble that's dapper and wow-worthy, reach for a navy geometric overcoat and brown dress pants. To inject a more laid-back feel into your getup, throw in brown suede cowboy boots.View Details
Men's Dark Brown Suede Cowboy Boots, Grey Ripped Jeans, Black Crew-neck T-shirt, Brown Leather Shirt Jacket
Inject personality into your day-to-day casual fashion mix with a brown leather shirt jacket and grey ripped jeans. Balance your ensemble with more laid-back shoes, such as these dark brown suede cowboy boots.View Details
Men's Dark Green Leather Cowboy Boots, Navy Jeans, Red Crew-neck Sweater
If the setting allows a laid-back menswear style, make a red crew-neck sweater and navy jeans your outfit choice. If you wish to immediately dress down your look with a pair of shoes, why not complement your ensemble with a pair of dark green leather cowboy boots?View Details
Luka Sabbat wearing Black Leather Belt, Beige Snake Leather Chelsea Boots, Beige Plaid Chinos, Light Blue Long Sleeve Shirt
To create an off-duty ensemble with a modern take, pair a light blue long sleeve shirt with beige plaid chinos. For a fashionable hi/low mix, add beige snake leather chelsea boots to the equation.View Details

How To Wear High Cowboy Boots

Western-inspired ankle boots are the lite, more wearable version of traditional cowboy boots that are distinguished by at least mid-calf height, a slightly angled heel, no lacing and decorative embroidery.

High cowboy boots are certainly harder to pull off without going full-on country. If you’re asking yourself whether you can pull off cowboy boots in the city or not, you probably shouldn’t try and save them for a country bar or a day at the ranch. If you have the required confidence and swagger though, the on-trend way to wear traditional cowboy boots in the city is by tugging loose-fit jeans into them and pairing with a t-shirt or a pullover and a jacket for effortlessly casual Americana style.

Men's Black and White Leather Cowboy Boots, Charcoal Jeans, White Crew-neck T-shirt, Black Denim Jacket
This pairing of a black denim jacket and charcoal jeans is a safe bet for an outrageously dapper outfit. And if you need to instantly dress down this ensemble with a pair of shoes, why not complement your ensemble with black and white leather cowboy boots?View Details
Men's White and Brown Leather Cowboy Boots, Light Blue Jeans, White and Black Print Crew-neck T-shirt, Black Overcoat
Combining a black overcoat and light blue jeans is a guaranteed way to inject a refined touch into your closet. To inject a touch of stylish casualness into this ensemble, add white and brown leather cowboy boots to the mix.View Details
Men's Black and White Leather Cowboy Boots, Light Blue Jeans, Black Fluffy Crew-neck Sweater, Grey Plaid Overcoat
When the occasion calls for a refined yet cool look, consider wearing a grey plaid overcoat and light blue jeans. Black and white leather cowboy boots are guaranteed to give a dose of stylish nonchalance to this outfit.View Details
Men's Black Embroidered Leather Cowboy Boots, Charcoal Crew-neck T-shirt, Burgundy Suit
Combining a burgundy suit and a charcoal crew-neck t-shirt is a surefire way to infuse your styling routine with some masculine elegance. Want to go easy when it comes to shoes? Add a pair of black embroidered leather cowboy boots to the mix for the day.View Details
Men's Burgundy Leather Cowboy Boots, Blue Jeans, Blue Denim Shirt, Navy Denim Jacket
Showcase your prowess in menswear styling in this off-duty combination of a navy denim jacket and blue jeans. Finishing with a pair of burgundy leather cowboy boots is the most effective way to infuse a more relaxed finish into this ensemble.View Details
Jared Leto wearing Pink Suede Cowboy Boots, Gold Jeans, White Crew-neck T-shirt, Light Blue Denim Shirt
The combination of a light blue denim shirt and gold jeans makes this a neat laid-back menswear style. Let your styling chops really shine by completing your look with pink suede cowboy boots.View Details
Men's Black Leather Belt, Brown Leather Cowboy Boots, Black Skinny Jeans, Brown Snake Long Sleeve Shirt
If you're in search of a casual yet stylish ensemble, wear a brown snake long sleeve shirt with black skinny jeans. To inject a dash of stylish casualness into this outfit, add a pair of brown leather cowboy boots to your outfit.View Details

Lil Nas X Wearing High Cowboy Boots

The “Old Town Road” singer looks good in a head-to-toe country look wearing a cowboy hat, a western shirt, jeans and naturally finishing off with a pair of cowboy boots.

Lil Nas X wearing Black Wool Hat, Black Embroidered Leather Cowboy Boots, Black Leather Jeans, Black Leather Long Sleeve Shirt
Why not make a black leather long sleeve shirt and black leather jeans your outfit choice? As well as super comfortable, both pieces look amazing when combined together. Add black embroidered leather cowboy boots to your look to immediately amp up the style factor of your ensemble.View Details
Lil Nas X wearing Grey Leather Cowboy Boots, Light Blue Jeans, Multi colored Print Long Sleeve Shirt
Extremely stylish, this relaxed combination of a multi colored print long sleeve shirt and light blue jeans provides with countless styling opportunities. Why not take a more relaxed approach with shoes and complement your outfit with a pair of grey leather cowboy boots?View Details
Lil Nas X wearing Black and White Leather Cowboy Boots, Black Chinos, Black Turtleneck, Black Double Breasted Blazer
Infuse an elegant touch into your day-to-day lineup with a black double breasted blazer and black chinos. Add a pair of black and white leather cowboy boots to the mix to inject a hint of stylish casualness into this ensemble.View Details
Lil Nas X wearing Black and White Leather Cowboy Boots, Light Blue Jeans, Green Print Sweatshirt, Green Overcoat
A green overcoat and light blue jeans are the ideal way to introduce extra elegance into your casual rotation. Let your sartorial credentials truly shine by finishing this ensemble with a pair of black and white leather cowboy boots.View Details
Lil Nas X wearing Black and White Leather Cowboy Boots, Tobacco Leather Chinos, Beige Knit Turtleneck
A beige knit turtleneck and tobacco leather chinos are a nice combination to have in your casual repertoire. To introduce a mellow vibe to your outfit, add black and white leather cowboy boots to the equation.View Details

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