A guy getting into leather must have boots. Tall, black boots are most common, and look best with leather gear, especially when the gear is tucked into the boots and you can see the boot shafts.
It may be an obvious point, but must be made, as quoted in my Guide to Leather Gear: Boots are essential for anyone getting into leather. Sneakers worn with leather just look silly -- even black ones. But you do not have to spend a fortune. Usually those first starting out get a pair of plain black harness boots, which are readily available from a variety of on-line retailers. You may want to consider a pair of engineer boots, which have a more "tough-look" style. The best and most affordable choices are made by Chippewa, Carolina, or Red Wing. Some guys just wear plain black combat boots that you can find at any Army-Navy surplus store. All are fine -- but the point is that if you are going to wear leather, you must have boots and no substitute.
Usually someone who is interested in leather already has boots, but just in case you don't, this is where you must begin. I know from reviewing the logs of my website, many are looking at the tall cop boots that I have. But also, many look at the simpler black harness boots, too. And plain ol' harness boots will work fine with leather. That style of boot gives a masculine "biker" appearance.
It is not necessary to buy a pair of Dehner Patrol Boots. While boots made by Dehner are legend, unfortunately, the legend has worn thin as the stock boots are made for pencil-thin-legged guys and the shafts of the boots are made with a plastic material called "Dehcord" which cracks and breaks. In order to wear Dehner Boots with leather or a uniform, you likely will have to have them made custom to fit, which can be done, but at a cost of about US$800 when made of European calf leather (a much better, longer-lasting option). Don't get them for your first foray into the leather community. Invest wisely in alternatives with which you will be happier and more comfortable.
Instead, for cop-style boots, consider Chippewa Hi-Shine Engineer Boots which have a classic, masculine design, are made of all leather (including a leather lining), are exceptionally comfortable, and are affordable. (Go to Stompers Boots of San Francisco to get them. It's easy to order from them on-line from anywhere in the world.) Consider this: if you intend to wear them with leather, order them one size smaller but in EE width. A wider Chippewa Boot has a wider calf circumference, which will accommodate leather more comfortably (as I am wearing, photo right).
There are a number of decisions one can make regarding the types and styles of boots to get and wear. First off, you should plan to wear them often, rather than just once a year to a leather event. Therefore, the boots should fit well and be comfortable. If you have not had your foot measured for shoe size in a while, go to a shoe store and get measured. Feet tend to get wider and spread as one ages. Sneaker sizes are not equivalent to boot sizes. Go get measured!
I tend to get boots that fit my measurements, which is a standard 9-1/2D. However, in the past few years I have been getting a 10D because I plan to wear the boots for a long time, and anticipate that my feet will get wider as I age. I don't want to end up with boots that I invested in purchasing that I can not wear. Meanwhile, I use gel insoles and thick cotton-wool combo socks to accommodate the extra room and absorb sweat.
Another major concern about fitting boots correctly is the measurement of both the lower leg and the calf circumference. Here is what I say about it in my Leather Gear Guide:
Lower leg: Custom gear may include custom boots. If you order custom boots, a critical measurement is the distance between where your knee bends down to the heel across the back of the leg. You don't want boots that are so tall as to rub the back of your knee when you sit down, else suffer a terrible sore.
Calf circumference: Also called "calf width," one very important matter to ensure custom boots fit right is knowing the circumerference of your calf. Stock boots may fit okay in the foot, but if they are too tight on the calf, you will be uncomfortable, or you may not be able to pull the boots on tall and straight. If you plan to wear boots with leather or cloth uniform breeches inside them, get that gear on first, and then have measurements taken over what you are wearing to accommodate for the thickness of the leather or fabric. Wrap a tape around the calf about 4" below the knee, and again about 8" below the knee.
Custom Boots are made to measure not only your leg and calf, but also your foot. A quality custom bootmaker, for example Wesco Boots, will have a form for that purpose. Have a friend trace both feet onto a template that is sent to the company from which you order the boots (such as Stompers) and that is used to make a pair of boots that will fit you perfectly. (BTW: DON'T order custom or stock boots directly from Wesco or Dehner; you can save 10% - 20% on exactly the same product if you order them through a boot specialty retailer like Stompers Boots.)
I have much, much more information on how I choose boots on this page of my website. Have a look!
Now, if you're serious about leather, start with the boots. Check back tomorrow for more on essential leather gear.
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