How to Match Every Boot Style With the Right Jeans

Boot in its simplest form is a type of footwear that protects the foot and the ankle. Believe it or not, shoes of this type have been around since 1000 BC. Now, jeans as we know them emerged in the 1860s started being mass produced in the 1870s. But, if you know your fabric history, you know that denim originated from dungaree, which is a fabric that's been spun in India for hundreds of years. Denim is a variation of dungaree first produced 200 years ago in Nimes, France. All right. So, enough history. When it comes to finding the perfect pair of jeans for your boots, what do you think the most important measurement is? Waist? Inseam? Nope. Keep guessing. Maybe the rise or maybe the outseam length? Nope. The answer, gents, is the ankle width. Now, with most modern denim, we're going to see on average a 14-inch ankle diameter. Although, for some skinny and extreme tapers, we're going to see under 12 inches. And for some wide cuts out there, over 16 inches is going to be common. Now, the million dollar question is what's the perfect width for you? Well, the answer to this question is actually pretty simple. Take a pair of jeans that you already love, a pair of jeans that already work with the boots in your wardrobe. Lay it out flat and then measure the ankle width. As you can see here, I've got a wide variety of options in my wardrobe ranging from just over 6 inches to just over 8 inches. When it comes to my personal taste, I like just over 7 inches in the ankle width, so a total of just under 15 inches. You see how I got that? You just take that flat measurement and multiply it times two. Gents, I can't stress this enough. Knowing this one measurement is going to make it so much easier to find the perfect pair of jeans to work with your boots. Now, unfortunately, not every manufacturer lists this on their website, but many do. And if you're going and you're shopping in person, what you can quickly do is take a measurement tape with you or ask for one there at the store and measure that ankle opening before you even try the trousers on. So, now, let's get into the key fundamentals to matching boots with jeans. First up, fit matters. It doesn't matter how stylish those jeans or those boots are. If they don't fit you if you're not comfortable in them, then it's just not a good deal. So, you want to try on the boots. You want to make sure you give time to break them in. So many people buy a pair of boots and then they just wear it without giving it time to say, hey, is this actually a good fit for me? Especially if you're a younger man, maybe your feet are still growing, which they do up to the age of 21. Or if you gain or lose weight, you really want to make sure you've got footwear that fits your body. Denim, the same thing. And I know you think you know your size, 32-32, 34-34, whatever it may be, it's going to be different with different brands. And so, find the brand that works for you. Some of you guys, it's going to be Levi's. Some of you guys out west, down south, maybe you're more Wrangler men. For some of you guys, it's going to be APC. And some of you denim heads are going to be willing to spend hundreds if not a thousand bucks to get that high-end Japanese stuff. Now, as a style guy that gets into fabrics and quality made clothing, I do see where some of those more expensive jeans are going to be perfect for certain guys. But, I think for the majority of men, what you want to look at is find a brand that just works for you and you can get great denim in my opinion easily under $150. And if you wait for sales and you know where to look, you can find great deals under $50. Just remember to get the right fit because even saving 90% on a pair of jeans that don't fit, that is still a bad deal. Now, the idea of proportion was identified by artists thousands of years ago. And it's something as human beings we naturally use to be able to see if something just looks off. And, gents, I'm here to tell you, violating this rule can have disastrous consequences when it comes to your look. Seriously, in cartoons, drawings, have you ever wondered what makes a character look powerful versus making a character look cute? Cute characters for the most part have overly sized overly proportioned eyes, heads, and other parts of the body. So, how does this play into matching your boots with your jeans and making sure you've got a great look? You want to make sure that your boots or your jeans are not oversized or undersized with the jeans or the boots you're trying to match them with. Now, let's take these boots right here, powerful, strong from the sole to the upper. The leather, these are made from a very stiff heavy leather. These need to go with a pair of jeans that have just a bit of give, a little bit of extra material. You don't want to wear these with skinny jeans, it's just going to look disproportional. Now, what pair would better suit slim jeans? Right here, we've got a very sleek design. We don't have as much as large of a sole. We've got an upper that just is cleaner and overall isn't as bulky. This is going to work better with a tapered jean design. Now, some of you guys may be saying, come on, Antonio, what are you talking about? By definition, all jeans are casual and all boots are casual. True, but not always. So, what I mean here is, yes, all jeans are casual, all boots are casual, but there are different levels. There are ultra casual jeans, there are business casual boots. And you don't want to mix those two because the combination is just going to look off. Seriously, these boots right here are more of the business casual type and they would work great with dark-colored denim, but they're not going to look great with lighter colored denim that has rips and tears in it. Or let's take this casual boot right here. This is going to be something that's very difficult to dress up. Why? Because of the overall style, the history. This is more of an alpine hiking type of boot design and, therefore, isn't going to be something you could actually wear with a sports jacket. Now, this jodhpur style is actually incredibly versatile. And the big thing here is being able to pull this off with confidence. Can you dress this up with a sports jacket? Yes. Can you dress this down with distressed denim? Yes. It's all about the wear and knowing that this is about, yeah, if you're wearing this, you feel and possibly look like a rock star. The point, if you're just getting started, if you're a style beginner, try to keep formalities with the same level of formalities. If you're a style expert, if you've got the confidence, understand that you can actually break that rule and bend it to serve you. Now, the general rule here is any denim that you wear with boots can on average be about an inch longer than if you're going to wear that same denim with sneakers or, you know, god forbid, running shoes. But, seriously, gents, don't be wearing your running shoes with jeans. These are meant to be worn when you run. Makes sense, right? Now, with boots, usually the longer hem is okay because we've got a larger proportioned shoe. So, if you've got a bit of rise, a little bit of bunching at the bottom, that's not always a bad thing. You will find different types of boots, though, are suited to a cleaner, tighter, shorter hem. And it's oftentimes going to be ankle boots. Lower boots, similar to any type of sneaker, because they're lower, they're not as going to be large proportion, it just looks better if you've got the trousers cut raised up just a bit. And, again, this is something you can do yourself or you can take it to a seamstress or tailor to make sure you get the right length. Now, gents, quick question for you. What do you think is the perfect style of boot to wear with denim? We've got our own thoughts here at Real Men Real Style, but I would love to hear from you down in the comments. Do you think it's Chelsea's? Do you think it's dress boots? What style in particular do you think is best with denim? I'd love to hear from you down below. And, of course, let's not forget color when it comes to matching boots with jeans. Now, me personally, I love the brown-blue combination. Incredibly easy to match, it looks good in a variety of situations. And when it comes to denim, it comes in a wide variety of blues from true blues to indigo. When it comes to boots, a wide variety of browns, light brown, dark brown, variations in between that use a little bit of each. This right here just makes it so simple I know in my wardrobe to be able to pair the combination. Black, on the other hand, does work with blue denim. It's going to be a more formal a darker color. That being said, mixed with a boot design, this does make it a bit more casual. I do think it's a little bit harsher of a contrast, so harder to pull off. But, if you've got gray jeans, if you've got let's say a maroon jean, if you've got a light color jean, you want a high contrast, black may be what you're looking for. That being said, don't shy away from unique colors or materials. You can go with a blue suede like Elvis did. Maybe you want to go with something that is a gray, a silver that is just going to stand apart, but the design is timeless and simple. The black right here mixed with that dark indigo is going to give a very streamlined look. People are going to be able to look you up and down. They're not really going to focus much on the feet, which may be the whole look that you're going for. It's going to be a little bit dressier. That same denim with these boots right here, all of a sudden the attention is going to be on the feet. Maybe you do want that because these are great looking boots, you want to show off the suede, but understand that's also going to make the outfit a little bit more casual. The point here is to understand the power of color of contrast and be intentional in the message you're sending. All right, guys, really quick. A lot of guys make a mistake. They think that just watching a video like this on YouTube is somehow going to make them an expert. Straight up, gents, you have to take this information and put it into action. And one of the best ways to motivate yourself to take action is to put yourself in a community, in a group of like-minded warriors taking steps to improve their image, their presence, their presentation. And you can find all of that over at our community at School.com. Over in our school community, we've got detailed classes, we host challenges, and you can meet and engage with like-minded men taking steps on a daily basis to become their best self. So, gents, instead of saying Sunday, how about you say day one and join our community? I'm putting the link down in the description in the comments or you can just go directly to School.com. So, now, let's get into the specifics. I'm going to assume that most of the jeans we're talking about here are dark denim. Now, of course, you got tons of options. You could go with black denim, you could go with a red denim, you could go with a gray denim, which is actually underused and can look really good. Point being, you got tons of options when it comes to colors. I'm going to go with the most classic, just that classic dark denim that I think every man should have in his wardrobe and for Chelsea. So, you can go with black, there's a wide variety of different Chelsea boots out there. But, the type and the style of jeans I'm going to look at are going to be either a slim or a tapered cut. You could also go with a straight cut. What you want to avoid though is going to be a loose baggy cut or even a boot cut. Yes, these are boots, but most boot cuts are made for western boots or boots that are going to have a larger thicker shaft at the top. Chelsea boots fit a little bit closer and depending on the style of Chelsea boot, it could be a dress Chelsea boot. Now, this one because of the sole, I know it's going to be a little bit more casual, so possibly I could get away with a pair of boot cut jeans. But, again, you want to try them on in general though. Straight cut I think is going to work for the majority of men trying to look good in a pair of Chelseas or you could go for a tapered cut if it's a little bit more of an elegant Chelsea. Next up, we've got the chukka. Very similar to the Chelsea in design, but notice we've got the lacing and it is going to be more casual. Now, the jean styles, they're going to work with chukka very similar to the Chelsea. You can go with that slim tapered cut, but, again, it's going to be the straight cut. You want to have a little bit more of an opening at the bottom. That being said, most boot cuts are probably going to be too wide especially if it's a modern boot cut that's coming in this looser clothing that we're seeing is trending right now. If you go with a classic boot cut, one that maybe came out about five to ten years ago, again, you can go and measure the openings, you can try this up. And that's what I recommend. Most of these brands selling jeans, they've got their own models that they use and their measurements. One could have a boot cut with an opening of 14 inches at the bottom, almost bell bottoms, you know, 15 inches. Other ones are going to have more like 12 to 13 inches, which could work for a pair of chukkas like this. So, now, let's talk about boots that actually work with the boot cut. Both of these right here are going to be heavier, are going to be more casual. And because of the length of the shaft, not necessarily the thickness, all both of these right here would work fine with a boot cut. Maybe not too wide because it could start to envelop the whole boots, but in general because of the size, because of the clunkiness, the build of these boots right here, they're not going to be dwarfed by that opening at the bottom. You could also wear straight. And I think straight jeans for the majority of boots is pretty much the perfect one to go with. I would be careful about going with a tapered fit. Definitely, you don't want to go skinny unless maybe you're going for that clunky foot. Yeah, if you're a fashionista, then what are you doing watching my video? You should be teaching this stuff. No, not for me, not my style, but I think this right here, either one of these, you could wear a boot cut and be fine. And as many of you guys could probably guess, a boot cut is going to work perfect for western boots. And this is originally what the boot cut was designed for. So, in brands like Wrangler and other western styles, we see a lot of boot cuts because cowboys need to be able to put their boots on and be able to cover the shaft. Now, you're going to see some people out there wearing the jeans in the shaft. I'm not going to recommend for the majority of men. Now, if you got a pair of handmade boots and you really want to show off the handwork, then I guess go for it. Now, that last style was a western boot. This is a roper. You're going to notice the ropers have a shorter shaft and usually not as wide of a shaft, not as pronounced. And this is going to be, again, perfect for the boot cut. The straight cut is going to work great. Slim or skinny jeans, yeah, you want to avoid. Now, what about baggy jeans? For most men, I'm not going to recommend that style. I know it's coming back. If I were to have to choose a pair of boots to go with, it would be something that's heavier a little bit more clunky. You could go with a hiking boot, kind of an explorer boot. You could also look at moccasin style boots. I love them because they're incredibly comfortable, but that larger toe box with the overall, you know, features the contrast in, you know, the design and everything right here, it makes the boots look a little bit bigger than they actually are. So, if you wanted to go for something that would balance out that looser fit, then these would probably be it. If you go with a relaxed cut, which is fine, especially for a lot of guys that just like a looser jean. And a relaxed cut is not the same as baggy and it's usually going to have a little bit larger of an opening, so a relaxed cut jean would work with either one of these. Straight cut, as always, will work with these right here. Boot cut would work as well. Skinny or, you know, tapered jeans, you'd want to be careful. You could possibly pull it off with the right style of taper or if you want one size larger. Next up, we've got the dress boot. As the name implies, this is going to be one of the dressier styles of boots out there. This pair right here, it has a bit of a brogue design, a brogue as many of you guys know, holes cut into the leather. This comes out of I believe it was the UK, maybe it was Scotland or one of those northern areas that's always starting fights up there. They said, hey, we're going to walk through these marshes and we want the water to be able to leave our shoes. So, that's where the brogues originated from. These are not going to go all the way through. It's more of a decorative design, but it is considered something really nice that makes it a little bit more difficult to clean. In either case, we've got one in suede, we've got one more in a polished leather right here. Either one of these straight jeans, of course, would work. But, maybe you could find a pair of tapered. You don't want to go for a tight taper. You want to go for something that fits maybe a little bit looser. Again, go with that dark colored denim, black denim right here mixed in with that brown. And if anyone thinks that brown doesn't go with black, just look at the soles right there. Look at how they're black. So, you can clearly see that black does go with brown. It's a really smart combination especially when you want to dress it up maybe with a sports jacket or maybe a really nice sweater during the winter. Skinny, I would avoid that type of jeans. And you could go maybe with a relaxed fit on these boot cuts. I think it would be too much for the beautiful I think more delicate nature of these boots. But, yeah, you could go with a pair of relaxed jeans. Definitely not, yeah, don't go with baggy. Now, what about the humble work boot? So, first up, don't be confused by the name. A work boot maybe 40, 50 years ago was primarily used for work. Nowadays, we see where you can dress them up, you can dress them down. You can wear them, of course, to work, but you can also wear them every single day as you're just exploring New York City. That's what I like about this style is it's incredibly versatile and it works with a wide variety of jeans. I mean this pair right here, I could wear with a pair of slim cuts, I could wear it with a straight cut, a loose fit jean. Heck, I'd even stretch it and say you could try to wear this with baggy jeans. I probably wouldn't be able to pull it off, but who knows maybe you could. I think the key here is finding the right style because this one right here a little bit more elegant, a little bit, you know, sharper looking, a little bit more delicate looking if you want to use that word. This one right here, just heavier clunkier. Why? Look at the sole. So, if you want to, you know, a pair of boots like this and you want to wear them with a bigger jean that has more, you know, excess fabric on it, then look for a larger sole. So, what video to watch next? Well, let's talk about the upper body. Guys, I got you covered how to correctly match jeans with a sweater. You got the boots down, let's talk about those jumpers, the sweater. Let's get that right. Don't mess this up, guys. I got you covered, boom, with this video right here. Oh, yeah.