Today I have a fun question for you concerning some clothing and of course Cowboy Boots. Below is another video posted by Jeremiah Craig on the subject of What kind of pants go with cowboy boots? Hope you enjoy!

Jeremiah will be going through several kinds of pants and deciding which ones go with cowboy boots and which ones don’t go with cowboy boots! His cowboy boot of choice when comparing pant styles will be his black Boulet boots as seen in the video. So stick around and see if your pants make the cut. Hold on to your saddle and let’s get started.

Here is a pair of boots pretty comprable to the pair in the video. A pair of Lucchese Black Kangaroo boots (on sale).

Khaki Dress Pants – Classic

Alright, so first up are the dress pants khaki style. They are classic and of course two classics have to go together, right? You have classic cowboy boots and classic khaki dress pants. For me, you just can’t go wrong with khakis and some classic cowboy boots.

If you take a look at them together, they hug the bottom of the boot really nice and they just go together right! It’s one of the classier pairs of pants that you can wear with cowboy boots. So basically I’m cool any day of the week wearing khaki dress pants with cowboy boots.

Jeremiah Craig – What Kinds of Pants Go With Cowboy Boots

Wearing Cowboy Boots With Skinny Jeans / Pants

All right, so next up we got skinny pants or skinny jeans’. Something Jeremiah normally wouldn’t wear (skinny jeans’) because he just can’t wear them with boots. Not a fan of the way that you see the “V” or the outline of the top of the boot or shaft of the boot with the jeans’. This is because they are “skinny” jeans’. Definitely not a fan of that.

Also, I’m not one to tuck my pants into my boots. I just can’t do it because it doesn’t feel right for me as a regular boot wearer to go around like this he says. I definitely 100% agree with that. You wouldn’t catch me dead tucking any pair of jeans’ into my boots! It looks weird, it feels weird. He does say girls can do it and I agree with that, but it’s just something he won’t do and I feel the same way. Another point that he points out is how it feels constrictive and a boot isn’t supposed to feel this constricted against your skin. I guess if I were to wear a pair of skinny jeans and had to wear cowboy boots, I would find a pair with a short shaft. In all honesty, that is the only way I could see that working out. There are some great men’s short cowboy boots out there and they have become insanely popular over the past few years.

In conclusion, I’m not a skinny pants or skinny jeans’ wearer with cowboy boots and I second that. To be truthful, I’m not a skinny jeans’ wearer at all. I wouldn’t wear them with sneakers, so of course you’ll have to make your own decision on this.

Golf Pants And Cowboy Boots

Next up are golf pants. Some people think golf pants are pretty silly or goofy looking. Yeah, I agree, they can be a little much for my taste. Not something I would do, but Jeremiah seems to love them! Is it just an excuse to wear silly pants? He goes on to say when you wear golf pants, you realize that they are amazing! Golf pants are really light, but also, they are “fricken” ridiculous! You just got to own the ridiculousness he says. They go awesome with boots too.

Don’t tell him that you can’t wear cowboy boots with golf pants because you totally can. It’s ridiculous but it f**king works. You know it doesn’t hog the top of the boot too much. They are a little baggy, but they are comfortable like I said. If you wear golf pants and cowboy boots, you will get attention I promise you!

Lol, I couldn’t agree more. I’m not a big attention hound so I will let you and Jeremiah stick with the golf pants while I stick to cowboy boots and jeans’!

Wearing Cowboy Boots With Shorts

This is for the guys, but do I even have to say anything for these? I mean cowboy boots and shorts just don’t go together like we talked about with the tight pants and tight or skinny jeans’. Now of course, this can work for girls. Actually cowboy boots and shorts look fabulous on girls in my opinion, but it doesn’t work for guys.  Jeremiah goes on to say “at least not for me”, but I’m going to say for all guys lol.

He goes on to say over and over that “this does not work” and that there just aren’t any words for this look. He’s 100% right and if you’re a guy, do the world a favor and do not wear shorts with cowboy boots.

Ladies, I don’t want to think we forgot about you, it just seems like you can wear about anything with cowboy boots. If you haven’t checked it out already, check out our article on dresses and cowboy boots!

Bootcut Jeans And Cowboy Boots

Finally, the old standbys, the bootcut jeans’! Bootcut jeans’ are made for cowboy boots. This is the reason why these jeans’ exist. They’re tighter up on the leg (thigh area) and then they flare out to make room for the top of this boot. I mean you just cannot go wrong as with the khaki dress pants you cannot go wrong with bootcut jeans’ when you’re wearing cowboy boots! Try a pair on and look how it flares out at the bottom. I just really like the look of that.

I love the bootcut jeans’ and you just can’t go wrong with them. I will always do bootcut jeans’ with cowboy boots.

Jogger Pants With Cowboy Boots

If you’re not familiar with what jogger pants are, they’re basically just sweat pants and khaki pants mixed together. Pretty accurate description I guess. The look anyway. They have an elastic band around the waist and also around the ankles. Because there are elastic bands down around the ankles, you have to tuck them into your cowboy boots. If you try to pull them over the shaft of your boot, it’s not only difficult, it’s just not going to work. It really looks ridiculous. Worse than the skinny jeans’ in my opinion.

It just feels weird and they are too tight in my opinion. Again, they are too tight and pants that are too tight with cowboy boots just doesn’t work for me. I said it earlier, I’m just one not able to tuck in my pants into my boot.

I’m not gong to ever wear jogger pants with cowboy boots. I do love jogger pants and would wear them with just about anything else like sneakers of course or even sandals / flip-flops around the house. I recommend them because they are super comfortable, just now with boots.

The Onesie And The Cowboy Boot

The only reason I’m including this here is because Jeremiah did in his video lol. I don’t own a onesie, I don’t sleep in a onesie, and I really don’t even know where I could get one. Here is Jeremiah’s take on it!

finally, I give you the onesie and the cowboy boot. Now you know the only time you’re going to be wearing this is in the middle of the night (not me) when something wakes you up outside. You think it’s a bear so you get your cowboy boots on, get out of bed, grab your shotgun and run out there like this. (I actually think we’ve seen this a couple times in some old westerns or hillbilly movies lol).

Then you realize it’s just grandma sleepwalking. You know, you put your boots on with your onesie for nothing! You go out in the cold, but at least your not barefoot out in the cold in the snow. You usher grandma back in carefully so as not to wake her from her midnight slumber walk and you go back to bed.

Yeah, that was kind of a crazy little story I guess, but I do have to give it a thumbs up. In that instance and that instance only, I can see wearing a onesie with a pair of cowboy boots.

Cowboy Boots With A Tuxedo

This is something that he doesn’t mention in his video, but I wanted to talk about. Cowboy boots and a tuxedo is actually a good look if you ask me. I have been to many a weddings where the groom and groomsmen have worn this.

A penguin suit with a nice pair of black cowboy boots like the pair he wears in the video look great together if you ask me. If you have some black dress pants in the closet do me a favor and get them out and try them on with a pair. You won’t be disappointed. It’s not much different than wearing them with a pair of khakis like we talked about above. Give it a try.

My Do’s & Do Nots When It Comes To Pants & Cowboy Boots

Well there you have it. You’ve probably asked yourself many times what kind of pants go with cowboy boots so I hope this helps out. I kind of think you actually knew the answer to most of these, but you never know.

To quickly go over it again, khakis are a yes with boots. Skinny jeans’ and shorts are a big “NO” when wearing any type of cowboy boots in my opinion. Golf pants are a surprising “YES” for boots, but not while you are actually golfing. If you golf, you will know the reason why for this. Bootcut jeans’ are of course a yes and my preferred choice when wearing any brand, style, exotic, you name it cowboy boot. A tuxedo is definitely a yes, but you might want to check with the bride first or significant other lol. Jogger pants get a thumbs up when relaxing around the house or wearing sneakers, but a big “No Way” with a pair of cowboy boots. Last but not least, the onesie gets a “Hell Yeah” but only if you are jumping out of bed to fight a bear or of course rescue grandma.

If you have any other questions or ideas on what or what you shouldn’t wear with cowboy boots, give us a shout out down below in the comment section. I would love to hear it and I hope this has helped you find something to wear with your favorite pair of cowboy boots!

The post What Kind Of Pants Go With Cowboy Boots? first appeared on We Heart Handmade Boots.