Leather Pants: Inside or Outside Boots

Search engines drive interesting results to this blog and to my website.  Recently, someone from Sacramento, California, searched a question, "Do leather pants go inside the boots or on the outside?"

Answer:  yes.

I am not being flip.  Well, yes I am but let me explain.

The choice to wear leather pants inside or outside boots depends on two things:

1. The look that you want to have.
2. The thickness of the leather.

I'll tackle this in reverse, because ultimately whether it is possible to wear leather pants (jeans, breeches) inside tall boots depends a great deal on the thickness of the leather from which the garment is made.

If you have very thick leather pants, then stuffing all that leather inside tall boots will likely cause it to bulge or bunch up at the knees and look dorky. You just can't get it all in there. The calf circumference of the boots you choose to wear (sometimes called "calf width") has a lot to do with that, too. If the boots fit you tightly, there will not be enough room for leather, particularly thick leather, to fit over your lower leg and allow you to pull the boots on so you end up with a smooth appearance of where the leather pants fit into the boots.

Ultimately, that's what you want: smooth, clean lines of leather meeting leather. This is what I referred to above by "the look that you want to have."

Wearing leather isn't rocket science. If the pants fit into boots smoothly, and that is the look that you are going for, then wear them that way.

Leather pants made as breeches are specifically made to be worn inside tall boots. Breeches become more narrow at the ankle, and usually have a closure like a zipper to fit them closely at the ankle. The tapering leather and closing holds the breeches down inside boots.

If you have leather pants or jeans with a regular opening at the bottom (that is, about 16-1/2" to 17" around), and if you want to wear them inside tall boots, then you have to wrap the leather at the bottom of the leg carefully around the ankle. Most guys pull socks up over the leather at the ankles to hold it wrapped there. Essentially, a sock wrapped around the leather serves a similar purpose as tapered legs with zipper closures -- it forms a way to hold the leather down smoothly so boots fit over the legs neatly.

If, however, the leather pants are long (that is, come down to your foot) and the leather is thick, you probably can't do that. You end up with a 1" to 3" mass of leather bunched up at the ankle. When you pull boots on, the extra leather presses against the foot, and may cause some pain.

A trick that I learned when I want to wear tall boots over leather pants is to pull the pants on, but leave them open at the waist while wrapping the leather at the ankle, pulling the sock over it, and smoothing it out. Then I will pull on my boots, stand up, and then pull up my pants, tuck in my shirt, close the fly, button or snap the pants at the waist, put on and close my belt.

I know this is not the usual way that men pull on their pants -- they put them on, close them up and tighten the belt, then they put on their boots. However, if you do it the way that I described, when you pull your pants up after pulling your boots on, the leather will smooth out at the knee and won't bunch up. The result is a cleaner, smoother appearance, which is ultimately what you want.

Now, to explore the searched question further: DO leather pants go inside or outside boots, with my answer being, "yes," not only does it matter what kind of leather pants you have and how thick the leather is, but it also depends on your confidence and self-perception. If you are afraid of what other people may say, call you "gay" or make jokes like, "playing cop today, are ya?" -- then you either need to develop more confidence and be prepared to respond to comments like that with a well-rehearsed reply, like: "yeah, aren't the pants and boots cool?" or "I like how they look" or "you know I'm not a cop, but I like the appearance" and just chill out.

If however, you are unable to develop that confidence level or are truly afraid of what other people may say, then put the leather and boots away, and reduce yourself to wearing jeans and sneakers and call it a day (but by all means, do not ride a motorcycle in sneakers!)

Life is short: wear leather!