How To Wear Boots With Jeans (For Men)

Boots and denim make a great combo — but you have to get a few things right.

In the world of men’s style, there are no absolutes. Anything can look good or bad depending on the execution and context, and that’s readily apparent when you think about pairing jeans with boots.

The combination of boots and jeans conjures up a few vastly different images. For example, you might picture a stereotypically outdoorsy look with a flannel button-down.

You might imagine a refined business casual outfit with Chelsea boots and a quarter-zip sweatshirt. Or you might just think of George Strait.

The point is that there’s a wide range of ways to style boots with jeans, and you can easily adapt them to suit your personal preference. (In other words, you’re not limited to the cowboy look). But in order to nail these different styles, you have to first understand a few key principles.

How to Style Boots With Jeans

Styling boots with jeans is pretty simple, but there are a few guidelines to keep in mind when pairing these classics.

Watch Your Proportions

A good rule of thumb is to make sure your jeans and boots are proportional to one another. This means that the slimmer your jeans are, the sleeker your boots should be. Consequently, the more relaxed your jeans are, the thicker your boots should be.

If you match, say, skinny jeans with huge combat boots, you’ll get the undesirable clown shoes effect. And if you pair billowy straight-cut jeans with slim boots, you’ll look like your feet are a few sizes too small for your body.

That being said, breaking this rule isn’t always a bad thing, but you have to do it very tastefully. 

For example, you can usually pair slim (not skinny) jeans with heftier boots. But if your boots and jeans are noticeably out of proportion with each other, your outfit is probably going to look not all that great.

Analyze Your Denim

You probably associate the boots and jeans pairing with two particular types of denim: slim dark wash jeans with ultra-tidy cuffs or lighter boot-cut jeans that completely hide the top part of the boot. And while these are still two popular types of jeans to wear with boots, they’re not your only options.

You can wear pretty much any style of jeans and still find a good pair of boots to go with them. The trick is to consider how the jeans are cut, what type of hems they have, and how dark or light the wash is. This will help you make sure that your boots and jeans have complementary styles.

For example, if you have dark jeans with a noticeable taper, you’ll probably want to go with a thinner boot. Similarly, if you’re going for a more laid-back vibe with medium-wash jeans that have frayed hems and wider leg openings, you’ll likely want somewhat chunkier boots (but ones that aren’t too large).

Match Your Formality Levels

For the most part, you don’t want to mix formality levels unless you’re going for an incredibly casual statement outfit — and even then, you have to do it the right way.

In general, darker-wash jeans and dress boots are considered more formal, while lighter-wash jeans and more rugged boots are more casual.

Keep in mind that most boots are more casual than formal. A few noticeable examples of dressier boots are Chelsea boots, Balmoral boots, Jodhpur boots, and some service boots and chukka boots.

Consider Cuffing

Most of the time, it’s a good idea to cuff your jeans when wearing boots. There are all kinds of ways to cuff denim, but for boots specifically, the double and pinroll cuffs are best.

If you opt not to cuff, then make sure your jeans don’t pile too much around the ankles. There should be a break at the bottom of your jeans so that the fabric doesn’t sag or cover up too much of the boot for a sloppy look.

And if you’re wearing boot-cut jeans or jeans with frayed hems, you’re better off embracing the character of your denim and not cuffing.

How To Wear Boots With Jeans for Men (10 Ways)

Now that you know the fundamental style principles behind styling jeans and boots together, get inspired by checking out these 10 outfit ideas.

The Classic Outdoorsy Look

While no style is truly timeless, this outdoorsy look comes pretty close.