How to Wear Men’s Boots With Jeans

Picture the scene... the cold, wet weather is starting to roll in, golden brown leaves litter the ground and it’s officially autumn. Surely it stands to reason that now is the time to invest in a new pair of men’s boots?

There are lots of different styles to choose from, whether it’s a smart-casual look you want to go for with a nice pair of men’s Chelsea boots, or it may be that a solid pair of lace-up boots are a more practical option for everyday wear.

All these different types of men’s boots are great, and there are plenty of ways to wear them, but given that jeans are a must-have staple in most wardrobes, we thought they deserved their own article on how best to pair them with boots.

So, how do you wear men’s boots with jeans? How do you ensure you’re matching them well? Should jeans be tucked into boots? Which men’s boots are casual and which are smart? There are plenty of questions that need answering, so we’re going to do just that.

Do Men’s Jeans Go Inside or Outside Boots?

Choosing how to wear your boots with jeans is entirely down to your own preference, however certain styles do lend themselves better to wearing them in a particular way.

A great example of this would be men’s walking boots. If you’re out there in the wilderness and you decide to wear jeans, then there are a few precautions that you might want to take. Jeans are made from cotton so are naturally very absorbent; to stop your jeans getting wet, the best option would be to tuck them in.

If, however, you’re out for a night on the tiles and you’re just not sure what kind of look you’d like to go for, consider the style of jeans too. If you’re opting for a slightly dressier boot cut style of jeans which are designed specifically to go over footwear, then going for a pair of ankle length pull-on boots that have a simple upper will look sleek and mean you’re not taking focus away from the rest of your outfit.

On the other hand, if you’d like to get a little more edgy with your look, why not try a pair of fitted jeans with a great pair of desert boots? In this case, turn up the cuffs on your jeans to give your outfit a vintage vibe. Add some funky socks to the mix and you’ve got yourself a real statement maker!

Best boots to wear with different jean fits

Skinny jeans

Skinny jeans are ideal for a sleek silhouette. Chelsea boots are the classic choice, providing a streamlined look that’s perfect for both casual and smart occasions. This combo has stood the test of time, worn by icons from Mick Jagger to Harry Styles.

For a more rugged or edgy vibe, military boots work beautifully. Pair with slightly distressed denim to add texture and personality. If you want a streetwear edge, chunky lace-up boots create a bold 90s-inspired aesthetic. Match them with an oversized bomber or baggy tee to complete the look.

Slim jeans

Slim jeans pair well with desert boots for a casual yet refined style. Their suede or leather texture adds subtle sophistication without overcomplicating the outfit. For smarter occasions, lace-up leather boots work seamlessly, especially in darker tones. Moc-toe boots offer rugged charm, perfect for weekend layering with a knit or casual shirt.

Straight-leg jeans

Straight-leg jeans are versatile and complement chunkier boots well. Work boots or hiking boots provide durability and comfort, ideal for colder months or outdoor activities. For a western twist, cowboy boots drape neatly under straight-leg denim, offering an authentic, stylish finish.

Bootcut jeans

Bootcut jeans require boots that slide comfortably under the hem. Dress boots are ideal here for a polished look, while western boots give an authentic cowboy-inspired style. Dark washes work particularly well for a sophisticated, urban outfit.

Tapered jeans

Tapered jeans are slim at the ankle, so you can pair them with chunky boots or high-top lace-ups. This creates a modern, streetwear-inspired silhouette that balances the slim fit of the jeans with bold footwear.

Best Men’s Casual Boots to Wear With Jeans

Knowing what looks smart and what would be considered casual is a tricky one to navigate. Often, not knowing which jeans will go with which style of boots can mean you don’t quite get it right for the occasion.

If you’re going to a winter wedding for example, you’d usually opt for a pair of clean leather boots with a slim sole and matching laces, which would work well with a dark denim such as indigo. Or, mix it up with a pair of mole skin jeans in a camel colour if you’d like to add a bit of flair to your outfit.

On the other hand, if you’re planning a day of fun stuff and want to keep things light-hearted with your outfit, go for stonewash or acid-wash jeans and a pair of lace-up boots or hi-top trainers. Going for a pair of jeans with a loose fit will allow for better movement throughout the day, meaning any activities you do should be comfortable and restriction free!

Men’s boots and jeans can be a tricky look to nail, especially if you’re not sure what look you’d like to go for. However, fortunately both are so versatile that it’s easy to find a look that works. Sticking to classic combinations such as smart pair of Chelsea boots with skinny jeans or desert boots and fitted jeans, will start you off on the right foot. That being said, there’s no harm in experimenting, so find out what works best for you!

Best Men’s Smart Boots to Wear with Jeans

Just as jeans can be dressed down for a weekend look, they can also be elevated with the right boots to create a sharper, more refined outfit. If you’re heading to a dinner, date night, or even a smart-casual office, these are the boots to reach for.

Chelsea boots are the go-to option. Their clean, fuss-free design means they sit neatly under slim or skinny jeans, instantly smartening up your look. Black leather works perfectly with dark denim for an evening outfit, while tan or suede versions are great for daytime polish.

Dress lace-up boots are another solid choice. Opt for a sleek leather style with a slim sole and minimal detailing, and pair them with indigo or black jeans. Add a shirt and tailored coat, and you’ve got a look that’s both stylish and effortless.

or something a little different, chukka boots strike the perfect balance between smart and versatile. Whether in suede or polished leather, they pair well with slim-fit jeans and a fine knit jumper for a more contemporary edge.

The key with smart boots and jeans is keeping things tailored. Stick to slim or straight-leg jeans in darker washes, and avoid distressed or overly casual denim if you want your boots to shine.