This was a good question that landed on my website: "What are the first pieces of leather gear that I should buy for IML?" For those who may not be familiar, "IML" refers to "International Mr. Leather," which is the largest gathering of the leather clan in the United States, held every year on Memorial Day weekend (last weekend of May) in Chicago, Illinois. By the way, this information also applies to those who choose to attend Mid-Atlantic Leather, which is the second-largest gathering of the leather clan. This event is held in mid-January in Washington, DC.
I noticed that google directed the question to my tutorial called "Air Travel With Leather Gear" instead of my "Leather Gear Guide." Had the inquiry gone to the latter tutorial, the reader would have been advised that, in my opinion, the first pieces of leather to buy when considering attending a leather event like IML are: 1) black leather chaps; 2) a black leather vest; and 3) black boots (of course!) Compliment this leather gear with a pair of Levis or Wranglers and some black t-shirts. Simple!
The great thing about chaps is that they are so versatile. You can put them on quickly, and they look good with a pair of regular jeans. You can wear the jeans when traveling, and while being a tourist. Chicago is a great, walkable town. There are a lot of things to see and do, and you might not want to wear leather when going to a museum, taking a stroll to view "The Bean," or out to eat.
A black leather vest compliments the outfit. You can wear a vest over a regular shirt, or if the weather is warm enough and you have the physique, you can wear it over your torso. Lots of guys do that at IML, from lithe gym-rats to bears to all in-between.
Black boots are de rigueur. However, if you will be wearing boots with jeans and chaps, you can get shorter boots if you wish because one doesn't really tuck jeans and chaps into boots. Doing so makes the boots look "stuffed" and often due to the thickness of material, the leather puffs out at the top of the boots and looks ... um ... "dorky." Shorter boots like Chippewa Harness Boots would be great -- those boots are very durable, very comfortable, inexpensive, and well-constructed. While Harley-Davidson harness boots are prevalent, IMHO those boots are cheap and poorly-made, because they are made in China by third-party companies under license by Harley-Davidson for the name. You pay twice as much for the name alone. Don't fall for it. Get good quality US-made boots by Chippewa or Red Wing and you'll be much happier.
Die-hard leatherdudes who have some means and money will have a lot of other leather gear. As you consider future investments in leather gear beyond chaps, vest, and boots, I would recommend: 1) a good-quality leather motorcycle jacket, 2) good-quality leather jeans, and 3) leather gloves. You can (and should) wear the jacket and leather jeans regularly, not just for IML or other leather fashion shows. The jacket and jeans are staples in many men's wardrobes.
Other stuff that is "out there" includes leather breeches -- which look hot with tall black patrol boots -- but good quality, custom-made breeches can be costly (on the order of US$400 - US$600). Leather shirts also are prevalent, but aren't as necessary in an emerging leatherman's wardrobe right away. I wear leather shirts often, but I'm the type of guy who wears his leather frequently as I go about my daily life. A leather tie and Muir Cap completes the outfit, but again, aren't necessary.
In my opinion, leather gear that you don't need includes: 1) a chest harness -- few guys can pull off the look well. Chest harnesses look good only on very well-built men with chiseled abs. If you don't have it, don't wear something that points out an out-of-shape body. 2) You don't really need gauntlets, leather shorts, leather jocks, or equipment like floggers, whips, or chains. 'nuf said... toys are what they are. Also, IMHO "strong" opinion: leather shorts don't look good on most men. (And Chicago in May can be cool, anyway.)
Two things to remember: 1) don't bring lots of gear with you -- just a few pieces to mix and match. Most airlines charge outrageous fees to check baggage, and even more outrageous fees for a bag that weighs more than their maximum allowable -- usually 50lbs (22.7kg). Also 2) the largest "leather mart" -- vendor displays and sales -- is at IML. You can buy gear there if you wish.
In summary, for the guy who is going to IML for the first time and is looking to acquire some leather gear -- get chaps, vest, and short harness boots. You'll fit in fine and what I'm recommending is affordable. (However, be sure to read my thorough explanation about the differences between "cheap chaps" and "great chaps" because if you buy cheap chaps, it will be obvious that you're a newbee on a tight budget.)
Life is short: enjoy your leather!
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