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Should jeans be worn inside or outside of boots?

It is a style question, a fashion decision, a huge clothing debate. Should jeans be worn inside or outside of boots? The answer depends on many factors, things such as what kind of jeans you’re wearing, what kind of boots you’re wearing, what kind of stuff you’re doing when you’re wearing them and where you’re going to wear your boots and jeans. This question is all about fashion, practical style, personal preference…and what kind of jeans are hanging in your closet. It’s time to decide where you stand on this style debate.

Arr, Matey

Some fashionable people have a quick criticism for anyone who tucks their jeans into their boots: what are you, a pirate? And it’s true that this look is very much associated with the style of pirates during the Golden Age of Piracy in the 1700s. Watch a movie or a TV show featuring famous names like Blackbeard and you will very likely see this look worn frequently. Of course, they aren’t wearing jeans with their boots, but the pants are very much tucked into the boots and the joke is still made about people who choose to wear their boots outside of their jeans.

Close up of boots and jeans

But pirates had it right when they wore this look. They weren’t the only ones to do so. For a lot of casual attire, including riding clothes and hunting clothes worn in the 1700s and 1800s, pants were worn inside the boots to offer protection for the legs. It was also quite common among sailors of all types. They kept their pants inside the boots to protect pants from the spray of the water splashing up onto the deck. So when someone says that tucking jeans into boots is a fashion problem, they’re wrong. This look has probably been worn longer and more often than wearing pants outside of boots.

Is this look stylish, though? After all, you’re not a pirate in the 1700s. So do you actually still have a reason to wear your jeans inside your boots or does this look silly and outdated?

Is There a Good Reason?

Actually, there are many practical reasons why you might want to tuck your jeans down into your boots and looks be darned. On these days, wear slim fit or skinny jeans that are cut closer to the legs. This allows your jeans to fit into your boots much more easily.

Tying boots close up

If the weather is snowy and cold, or if there is a lot of slush on the ground, tucking your jeans into your boots will save you a whole lot of discomfort. Your jeans stay dry while you slog through all that yucky stuff in the boots, which by the way must be high enough to protect you from all that ice and wet that’s outside.

How the Look Began

However, dust and debris from the trail is the primary reason why this whole thing of tucking jeans into boots started to be a thing. It’s a look that goes back to the earliest pairs of jeans. The official patent for jeans was registered in the 1870s by Jacob Davis, a tailor and by Levi Strauss, a retailer. Davis had been asked to create a pair of tough work pants for a local miner in Nevada. He collaborated with Strauss on the type of fabric to use and came up with the idea to add copper rivets to the stress points of the pants.

The rest, as they say, is history. Jeans soon became the work pants of choice not just for miners but also for ranchers, who tucked the bottom of the pants down into their boots to protect against the dirt and dust on the trail, to say nothing of the brush. The jeans kept the pants from snagging. To this day, it is common to tuck jeans into cowboy boots in particular. This creates a distinctly western look that is still popular in Texas, Arizona and other southwestern states.

The Right Way to Tuck Jeans

It seems simple enough to tuck your jeans down into your boots. However, there is a bit of an art to choosing the right jeans to wear and getting them tucked inside smoothly so that you get a comfortable fit.

Wearing the right jeans is key. You don’t have to find the tightest pair of skinny jeans out there to find a good pair of boots that can be tucked inside boots. Actually, you want to have a little bit of moving room so that you can maintain a comfortable fit all day and all night. There’s an easy way to test the fit of your jeans if you plan on wearing them under your boots. Pinch the fabric of the jeans right below your knee. You should be able to pinch about an inch and a half of fabric. If you can pinch a lot more or a lot less, find a different pair of jeans.

Wearing boots outside close up

That’s not all. You need to be careful about the bottom of the blue jeans. You also want jeans that aren’t wide and flaring at the bottom. Even boot-cut jeans, which are made to fit over boots but don’t flare, could give you trouble. Look for slim fit, straight fit and skinny fit styles if you plan on wearing your boots on top of your jeans.

The boots are also key. You want a pair that is above ankle length at least, and mid-calf is more of a comfortable length if you want to wear this look. The boots also shouldn’t be extremely snug against your legs. After all, you need some room available in there for the jeans. If you can comfortably insert two fingers inside the top of the boots and move them all the way around your leg, you should be fine to tuck your jeans down into your boots.

Put your jeans on first and smooth them down, pressing them close to your skin. Cuff them up once. A nice, long cuff will do. This will keep the jeans from sliding down over your feet and creating discomfort, which they absolutely will if you don’t cuff.

Put on your boots next. Try to keep the jeans smooth and pull the boots on around them. Once the boots are on, gently pinch the fabric of your jeans above the boots and give it a small tug. Your legs need a little room to bend, after all. Lace up the boots, if needed, and stand up. Take a few steps, bend down a little bit, bend over, sit down and get the fit and feel of the jeans and boots right. Now, you’re ready to go!

Isn’t There a Good Alternative?

If you are adamantly against tucking, there are other ways to wear your jeans to protect them from the bad weather outside. Instead of tucking jeans inside boots, you can cuff them. When you’re wearing tall boots, above ankle-high, you can cuff your jeans up a little higher than you ordinarily would. This means you can do a double cuff, rather than a single. Essentially, you’ll be styling your pants so that they become capris.

Close up of work boots

This has a similar effect to tucking jeans inside the boots, as it will protect the bottom of the jeans and keep them out of the way of wet puddles, snow and other weather issues. This double cuff design will also allow you to show off your boots, always an added benefit to wearing boots outside of jeans. The double cuff, however, allows you to avoid tucking if you just don’t like the way that looks or feels.

But is it Fashionable?

It’s been proven, by now, that people are going to tuck their jeans into their boots for all kinds of reasons. There’s a way to do it to keep it looking good and smooth and fashionable. But just because you can wear this look does not mean that you should.

By the “rules” of dress codes, the jeans-inside-the-boots look should not be worn for any formal occasion. Not ever. First off, you should not be wearing jeans at a formal event. Tucking suit pants into boots…you should know not to do that!

Tucking jeans into boots started as a practical choice, so this is a look that is associated with casual wear. It’s hard to pull this off even as a semi-formal look. But as casual wear…well, it works some of the time.

If you’re actually riding a horse or hiking a trail, tucking jeans into boots is a smart choice and doesn’t look out of place. You can get away with this style choice for many outdoor casual events. But for indoor events, it’s a bit trickier to wear this look well. Try to save it for very laid-back events only, such as hanging out with close friends.

Wearing Jeans Outside of Boots

So…wearing jeans outside of your boots is still okay, right? This look is pretty much accepted across the board, whether you’re dressing casual or semi-formal. However, jeans still aren’t really formal wear so you’re going to have to change before you hit that red carpet.

Close up of boots while standing outside

Also, this just won’t work with skinny jeans. It’s not possible so please don’t try. However, boot-cut jeans are specifically made to be worn over boots. Wide leg and flared cuffs also fit easily and naturally right over boots.

There are definitely different cuts of jeans that are easier to wear outside of boots and others that are easier to wear inside of boots. But the boots play a huge part in this look, too. Even the perfect jeans can’t help you if you’re wearing the wrong boots to pull off the look you want.

All About Them Boots

The type of jeans you wear definitely plays a role in whether you wear those jeans inside or outside of your boots. But there are different styles of boots that definitely work better with certain styles than others. Really, it’s all about the boots when you choose whether to go in or out with your jeans. Sometimes, the boots will totally dictate everything about how your final outfit looks.

Boots in History

Boots are actually one of the oldest pieces of fashion ever created…though they have changed quite a bit since the Stone Age. Boots were a necessity for ancient hunter-gatherers who roamed ancient plains and hills in search of food and shelter. They are still used as a piece of survival gear, actually. Military professionals around the world continue to wear boots because they are durable, highly protective and designed to keep the foot cushioned and secure on a long walk and tough hikes.

Walking in boots close up

Boots are the footwear you need if you’re going to be facing any tough terrain or bad weather. They certainly helped humankind’s ancient ancestors to survive the harsh conditions and dangerous terrain of Stone Age Europe and Asia.

Boots in Fashion

But today’s boots are also all about being fashionable, too. Even hiking boots and military boots have a chic look to them, and military boots have long since made the jump into popular fashion. Styles featuring combat boots are absolutely everywhere. They’re particularly popular in urban environments.

Some boots are about both fashion and practicality. The best example of this is probably motorcycle boots. They have buckles and zips and extras on them, but this is actually protective. The multiple straps and thick design of motorcycle boots shield the ankles and feet from impact and flying pieces of debris, dangers that motorcyclists face regularly.

Boots That Should Be Outside

Motorcycle boots are definitely made to be seen, however. You want to show these boots off. When motorcycle boots first became popular in American fashion in the 1950s and 1960s, it was a trendy look to cuff up the bottom of jeans. This kept the jeans out of the way while riding and it helped to show off those hot motorcycle boots, which were extremely popular with youth fashion at the time. You can honor this former style or you can tuck to keep on showing those boots, because they were meant to be seen.

Rothco 8'' GI Type Jungle Boot, Black, 9

Combat boots, which can be authentic military boots or any boots made in a military style, are definitely also meant to be seen. It is also common practice in military battle dress to wear pants tucked into boots. In fact, on military Battle Dress Uniform, commonly known as fatigues, there are drawstrings on the ankle to make it easier to keep the pants firmly tucked into those combat boots. These boots are definitely crying out to be displayed.

Women Winter Snow Boots Ladies Solid Color Non-Slip Plush Velvet Warm Mid-Tube Booties (Black, 6-Women-US)

Furry and fleecy boots, whether they’re meant to be practical or they are high-fashion winter boots, should definitely be outside of jeans. These boots are embellished in such a way that keeping them covered with jeans is going to end up looking odd because there will be a bulge in the bottom of your jeans where the boots are. Anything that is furry or fleecy is meant to be worn over jeans because these are meant to be warming, protective winter boots. Rain boots should also be worn over your jeans. Otherwise, why are you even wearing boots at all?

WHITE MOUNTAIN Shoes Women's Mazed Tall Shaft Boot, Black/Smooth, 8 M

Tall boots should also be outside your jeans because these boots are either made for style that is meant to be seen or they’re made for protection that is meant to safeguard your pants and your legs at the same time. So if your jeans are taller than your mid-calf, you should go ahead and get ready to tuck.

WOLVERINE mens Rancher St Work Boot, Dark Brown/Rust, 9.5 US

Cowboy boots are most certainly designed to be worn outside of your jeans, though they are worn inside jeans quite frequently as well. Though cowboy boots do have wider and looser openings than many other boot styles, they can be worn comfortably inside jeans if that’s your choice. This is really more of a style preference and if you really want to wear your cowboy boots with some wide leg or boot cut jeans, leaving the jeans on the outside is the only option. But rest assured that if you go with a more fitted jeans style and choose to tuck, it’ll look just fine.

Wolverine Men's Loader 6" Soft Toe Wedge Work Boot, Brown, 10 M US

Work boots are frequently worn outside and inside jeans. This is a safety issue. Keeping the jeans tucked into the boots keeps your feet, ankles and lower legs streamlined and prevents snags. Excess fabric can be a danger in the workplace, so keeping jeans tucked inside makes a lot of sense. However, in some workplaces, this extra safety step may not be needed. That means you can choose your look based on your own personal style.

In or Out?

So…where do you stand in this great debate? Are you a person who tucks their jeans inside boots or do you think this is a frightening fashion faux pas?

Unless you want wet jeans, you’ll probably need to wear your boots on the outside sometimes. No matter where you live, it’s hard to escape bad weather and gnarly hiking trails all the time. It’s a perfectly stylish and highly practical look for all sorts of casual outdoor activities. It’s also a stylish look when you pair it with several different styles of boots that are better when they’re displayed. So give this look a try and play around with different jeans and boots combinations. Because you decide what’s fashionable for you. And who knows? Maybe others will copy whatever looks you create.


Ariat – Should You Wear Jeans Tucked Into Cowboy Boots?

Men’s Health – Can I Tuck My Jeans into My Boots?

WikiHow – How to Wear Men’s Boots with Jeans