The 9 Most Stylish Men’s Casual Boots to Wear with Jeans

Dave Bowden

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Men's Casual Boots to Wear with JeansThere are few pairings more rugged, cool and classically masculine than a well cut pair of jeans and a well made pair of boots.

Whether you’re pairing your boots-and-jeans combo with a button down and a blazer or a field jacket and a sweater, there’s just something about the combination of denim and leather (or suede) that conveys a certain strength.

With the boots providing a sturdy foundation and the jeans giving off a classic sense of cool, this combo makes you feel like you can take on whatever the world throws at you—and throw it right back.

But with the menswear industry exploding in recent years, designers and brands have introduced dozens of new styles, variations and takes on classic men’s boots, making it hard to know which ones work best when rocking a pair of jeans.

In this post I’ll lay out the best, most stylish men’s casual boots to wear with jeans, and recommend a few sharp selections that will help you stand out.

Men's Casual Boots to Wear with Jeans

The Best Men’s Casual Boots to Wear with Jeans

Men's Casual Boots to Wear with Jeans

1. Leather Chukkas

Men's Casual Boots to Wear with Jeans

If you’re just starting to build your boot collection, start here.

Chukkas are a perfect blend between “dressy” and casual. Grab a pair with a sharp (ish) toe shape and you can wear them with almost anything.

They’ll look perfectly at home with a well cut suit, and a bit of sophistication to a t-shirt and jeans. (A rounded toe is generally considered more casual, and probably wouldn’t work with the suit.)

Sharp Selections:


2. Suede Chukkas

Men's Casual Boots to Wear with Jeans

Same boot, same toe shape, different fabric.

Suede chukkas get their own spot on this list because they serve a different purpose. While leather chukkas can be dressed up with a suit, the suede version is a little more rugged looking, and inherently more casual.

You can still pair them with a tee and jeans, but instead of a touch of sophistication, they’ll add some texture and toughness to your look.

Sharp Selections:


3. Cap Toe Boots

Men's Casual Boots to Wear with Jeans

You can find a cap toe variation of almost all the other boot styles on this list, but it’s worth calling out because of the way it alters the boot’s appearance.

When paired with a sleek looking toe shape, a cap toe adds an eye-catching and stylish bit of distinction that helps your boots stand out.

The handsome devil is on the details, and a cap toe is a great one to add to your arsenal.

Sharp Selections:


4. Combat Boots

Men's Casual Boots to Wear with Jeans
That was obvious, wasn’t it?

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Inspired by the boots worn by soldiers since (at least) the Second World War, combat boots immediately evoke toughness and resilience.

With a rounded toe, combat boots are a much more casual style, making them the perfect type of boots to wear with jeans. Pair them with a field jacket or a thick sweater for a look that’s as rugged as it is classic.

Sharp Selections:


5. Chelsea Boots

Men's Casual Boots to Wear with Jeans
Chelsea boots come in lots of different shapes and styles, but they all have a common trait that defines them as Chelseas.

Instead of laces, Chelsea boots feature an elastic band that runs down the ankle of the boot, allowing you to slide them on and off easily.

A lot of the same style options available on other boots (broguing, cap toes, etc.) can be found in Chelseas as well, so even if you despise laces, you’ll still have plenty of options.

Sharp Selections:


6. Dress Boots

Men's Casual Boots to Wear with Jeans

What makes a boot a “dress boot”?

In a word: sleekness.

Dress boots are designed to look as sleek and sophisticated as dress shoes, but provide the warmth, protection and stability of boots.

They could easily be worn with a suit and wouldn’t look at all out of place. Admittedly, that means they’re not exactly casual boots, but that’s what makes them so great to pair with jeans.

When you pair dress boots with jeans they can help elevate your look by adding a touch of sophistication that will help you stand out from the (casually dressed) crowd.

Note that toe shape is more important here than with any other style. Look for a well made pair with a toe that’s sharp enough to look formal, but not so pointy you’d expect to see it in the live action remake of Aladdin.

Sharp Selections:


7. Brogue/Wing Tips Boots

Men's Casual Boots to Wear with Jeans

Men's Casual Boots to Wear with Jeans
Image via James Bond Lifestyle

Brogues were originally worn by British hunters, and they still evoke the sort of rugged sophistication you’d associate with a manor Lord out with his hunting party—or, to give you a more modern reference point, James Bond one-upping his attackers in the Scottish highlands.

You can wear brogues in pretty much any situation where you’d wear combat boots. And while the brogues are (arguably) just as rugged as combat or work boots, they also add a dash of rakishness that helps elevate your look.

Sharp Selections:


8. Double Monk Strap Boots

Double monk strapped shoes are a staple in the wardrobes of many guys (especially dapper as hell Italians), but double monk boots are still something of a rarity—making them that much more appealing to guys who want their footwear to stand out.

Sharp Selections:


9. Single Monk Strap Boots

Single monk strap boots are essentially the sleeker cousin of double monks. While double monks are scene stealers that immediately draw the eye down to your boots, single monks are (slightly) less flashy, but no less dapper.

Sharp Selections:

Wrapping Up

If you’ve read this far (thanks for hanging in there by the way), you should have a strong understanding of which men’s casual boots to wear with jeans.

And while shoes (or in this case, boots) are the secret weapon of stand-out style, they’re still only one piece of the menswear puzzle. If you really want to learn how to out-dress the other guys and stand out from the crowd, you need to know how to nail the details—all the details.

Enter your email address below and I’ll send you a checklist that will help you do just that, outlining the Nine Details You Need to Nail to step up your style and put your best face forward.

Best Men’s Chukka Boots
The (handsome) devil is in the details

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Best Men’s Chukka Boots

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