Was Santa good to you and brought you a new pair of boots?  Perhaps you’re not accustomed to wearing boots that often, and want to know how to break them in?  Take some simple tips from a guy who has been wearing boots for well over 40 years as his exclusive form of footwear….

First, after you take the boots out of the box, make sure that there is no paper or cardboard stuffed deep in the foot of the boots. Better bootmakers do that sometimes.

Next, before you try to pull the boots on, check your feet — make sure you are wearing a decent pair of socks. The best socks to wear with boots are made of a combination of three components: cotton (for comfort); rayon/dacron/nylon synthetic (for longer wear and durability, as well as maintaining shape); and wool. Yes, wool. Why wool? Best for absorbing sweat and wicking it away from your feet, so your feel feel comfortable in boots all day long.

Contrary to popular myth, you do NOT need “boot socks” that come up high on your calf. If boots are made well, they will not rub on the inside of your legs, so regular socks (made of the three materials listed above) will work fine. Most of my socks are “gold toe” socks that I buy at KMart. I don’t spend tons of money on socks when what I can get at my local KMart will last me just as long.

Now — to your boots. Feel how stiff the shaft is. If the shaft is rather stiff — that is, if it doesn’t bend easily because the leather from which it is composed is thick, then I suggest breaking in the crease at the ankle manually. This is a rather simple but very important thing to do: hold the boot in one hand and crease the back of the boot shaft straight by bending it backwards, then forward, then backward again. (Please see this post and video for visual demonstration — it works the same for cowboy boots as it works for Dehner Patrol boots).

If the leather on the boot shafts is soft and bends easily, you can skip the manual ankle creasing method described above. But that manual creasing method is very important for stiff-shafted boots, because you want the crease to come straight across at the back of the ankle, and not at an angle. If the crease forms at an angle, it will probably rub against the back of your ankle inside the boot and cause sores. Once the crease forms it cannot be “retrained,” so get the crease right from the beginning.

Then hold the boot by the boot straps (or if necessary, use boot pulls attached to the boot straps) and pull one boot on one foot, then the other, by pointing your toes into the boots and just pulling. The boot should come on rather easily, but it may take a bit of a tug. That’s okay. New boots are stiff and aren’t easy to pull on or take off before they are completely broken in.

Stand up. However, before you walk in them, try wiggling your toes. Can you feel your toes inside the boots? Do your toes feel squeezed, or do the feet feel like they are swimming? Try flexing your foot up and down within the confines of the boot foot. Again, does it feel squeezed or like there is too much room?

If the foot feels like it is squeezed, then the boots may be too small. Even if they are marked your regular shoe size, there is no consistency from manufacturer to manufacturer on actual size. If the boots are small on you, you won’t wear them. See if you can exchange them for a half-size larger.

If the foot feels like it is swimming — that actually is a good thing. Get a pair of gel insoles (such as made by Dr. Scholl’s) that you can find at any drug store or well-stocked grocery store. Follow the directions to trim the gel insoles for the insides of your boots, then carefully fit them in. I think you will find — as I do — that gel insoles provide much more comfort and allow the boots to be worn all day long with comfort.

Then stand tall, walk proudly as the Boot-wearer you should be. Be careful where you step — for example, if you got new cowboy boots, they probably have all-leather soles, and therefore do not provide traction if you walk on wet, snowy, or icy surfaces. If you got motorcycle boots with a lug sole, you won’t have trouble with traction, but you probably will have trouble with mud and dirt getting stuck in between the lugs. If you don’t take your boots off before coming indoors, then once the mud dries up, it will fall out — and you’ll be in a situation that I have been in too often — the other half has words with you about being such a slob. (ooops!)

At the end of the day, use a boot jack or ask a spouse/partner/friend to pull the boots off. It’s hard for one person to pull of a pair of boots by himself if the boots are still stiff and not broken in.

Leave the boots in open air but out of direct sunlight for at least a day, so the boots can air out. Sweat from the feet and legs absorbs into the interior of the boot and takes a while to evaporate. If you don’t let boots “breathe” between wearings, then it may turn into a growth medium for fungus, which can be bad for your feet. So guys — if you like to wear boots as I do — use this excuse to justify having at least two pairs, if not more, of boots in your wardrobe.

Soon enough, you will find out that boots are far better for your feet, and you look better in them, too. You will find a place to donate your dress shoes and begin wearing boots to work each day of the year (as I do.)

For more tips and information on wearing boots (including wearing boots with khakis or business suits), visit my “Cowboy Boot How To” on my website.

Life is short: wear boots!