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How To Gear up to Win

By: LeatherWeb Sash Fashion

(Printable Copy)

With the influx of new young men interested in competing in leather contests, here are a few guidelines that will prepare you.

If you are shopping for leather for the first time, select your first items with care. If you are fortunate to have someone who is an astute leatherperson, have that person go with you. shop around for pricing and value for your money. As the old saying goes---YOU GET WHAT YOU PAY FOR!

What Should I Purchase First?

Leather is an expensive investment:

Invest in a good pair of leather boots, and a leather jacket. The jacket does not have to be in the hundreds of dollars. If you take good care of the jacket and condition it and clean it with several of the leather cleaners and conditioners on the market, it will last you for years to come.

With a jacket and boots, you are ready to venture out to your leather bar.

you have the basics. No need to worry about chaps and pants, levis and a black T-shirt will suffice. Next could be a leather vest. and then leather pants first, and chaps second.

Becoming a Contestant

  1. Remember first of all, the contest is a LEATHER CONTEST. The key word being Leather.
  2. Make sure your leather is CLEAN.
  3. Keep your boots POLISHED.
  4. The Length of pants or chaps, meet the instep of your boots.
  5. Select a harness, that fits your body. Slender built men should never wear a harness that is over 2 inches in width. Larger men should never wear a harness that is a half to 3/4 inches wide. The reason being, the harness will over power the person wearing it; or, on the other hand a larger person will look underdressed.
  6. The three most popular types of harnesses are the half harness, the chain harness, and the full body harness. The chain harness, and the 1/2 harness, resemble a king size X, and are the easiest to slip into. The full body harness on the other hand can be somewhat complicated getting into, if you unsnap or unbuckle the entire harness. Only unbuckle one side and generally it will slip over your head and you put your arm through the other side.
  7. Chaps are sold based on your thigh size, not your waist size since most chaps have expandable lace up leather thong strings in the back. When purchasing chaps for the first time, try to make sure they fit as tight as possible. Do not let a salesperson put you into a pair that fit like a pair of worn levis.if you do, then within a short amount of time the chaps will begin to look baggy, since leather does stretch, the same can be said for leather pants. Leather pants are sold by the waist size. In the case of both chaps and pants, they come unfinished at the length, and will be finished when you purchase them. Some stores will hem them via sewing machine, others will turn the additional length up and glue them for you. Remember to wear a pair of boots when being fitted for chaps or leather pants, to ensure the proper length when they are altered, do not wear tennis shoes!!

Formal Leather

Often there is much confusion on the area of formal leather. When the category calls for FORMAL LEATHER, it does not mean white tie and tails!!! it means your best dress leather. therefore it is not necessary to put on a pleated tuxedo shirt with studs! A leather shirt, will work just as well, and will look much nicer when you are on stage. Many clubs and leather organizations will wear tuxedo shirts and tie, at their installation of officers, anniversary dinners and other similar "STATE" functions. That falls under the area of Leather dress, and is required by many clubs.

Stay away from COSTUMES! Conan the Barbarian is OUT!!! Tons of chrome is also OUT!! You do not want to look like the front end of a 59 Buick!! Gain some insight from the old phrase- LESS IS MORE!


On the subject of sunglasses. Very poor move to wear sunglasses when on stage, If you must, (to complete your look) then have the good sense to take them off after you have been introduced, The audience and Especially the judges, want to see your eyes. Mirrored sunglasses are OUT!!

Biker Caps

If you are wearing a biker cap, and the bill covers half your face or your eyes then take the cap off!! so what if you are bald? No one cares!! BALD IS IN, AS ARE SHAVED HEADS!!

Borrowing Leather

If you must borrow a piece of leather from someone have the good conscious to return it in a clean manner! this especially applies to borrowing a leather jock!!! (the type with the strap up the backside!

Need I say more? If a leather jock category is what you are entering, then athletic WHITE supporters should be left in your gym bag!!!

For many leathermen, borrowing someone's leather is tantamount to high crimes and misdemeanors. Leather is expensive, and and a investment, and many will not lend their leather to anyone!!

Judges can usually tell if something is borrowed, simply by the way it fits you.

If you have borrowed a jock, from someone, and the pouch is too large, don't stuff it with tissue paper!! Your body heat, will cause it to become soggy, and there is nothing worse than to see pieces of white sticking out from the side of a jock!! The same applies to someone with a jock that is too small and one testicle keeps popping out!! The question most often asked is, "how can you be a leatherman, if you own no leather"?

When wearing chaps with a jock, make sure the straps of the jock are hidden under your chaps not riding high across your butt, like a "V" for victory sign!!

Leather Vests

The standard leather bar vest should hang no lower in the back than the bottom of your belt loops on your levis. Bar vests are designed to show off your wonderful chest. A vest can be worn over your leather jacket, especially if you are a club member and have a club patch on the back.


Armbands can be worn on ONE ARM you do not have to have two. The band does not have to be flashy. However, if you are wearing one, and you have a T-shirt on, then roll up or fold up the sleeve at least 1/2 inch above the band. for years many men thought you had to have a matching ensemble. Armband, wristband, and harness, all studded and all the same. Such is not the case, you do not have to look like an advertisement from Sarah Coventry jewelry!!!


Unless you are going to an afternoon tea party or the opera, gloves are a item of choice. Not however, to be worn with a jock and harness! Gloves can be carried in the back pocket of your levis, or in the epaulet of your biker jacket. long or short sleeve shirts worn indoors, and without a jacket look rather silly when gloves are added, since they serve no real purpose. This does not apply for the Mr/Ms FLAG Contest. Gloves are a requirement!!


The one item that every person should should invest in. You can make quite an entrance on a stage wearing a jacket, with or without something underneath. It is also permissible to take your jacket off and sling it over your shoulder while you work the runway!!!


Anyone can wear latex, not everyone should!!! If you decide to make an entrance on stage wearing a rubberized girdle, then do not accessorize!! latex speaks for it self!!! Make sure you have talcum powder,and latex polish with you. However keep in mind you are in a leather contest, and not attending a rubber play party! Some judges frown upon that when scoring!


Uniforms are terrific, and look good on most everyone, however, a uniform should be worn during the introduction of contestants, NOT during formal leather, or the selection of the winner!!! If you are wearing a uniform, make sure you have the entire uniform, and that all badges, stripes, and pins are in their correct places. Some judges have questioned contestants on the incorrect wearing of uniforms!!

Street and Cruise Wear

Much can be said about this area. ripped and torn jeans, shredded and torn T-shirts, are all considered cruise wear. In some cities, you can wear those outfits up and down the streets, but more often than not it is not the greatest idea, especially if you use public transportation. So just remember, when the category says cruise / street wear, think if it is something that you would wear down the street. Don't try to look cute and outrageous. Make sure the word "normal" enters your mind.


Gold chains, lockets, and ID bracelets, went out with leisure suits, the "A" TEAM and Mr. T!!!!! Leave that stuff at home!! Chains with padlocks bigger than your grandmother broach, should really be taken off (with the permission of your Daddy or Master) for the duration of the contest. The exception to that is if one is entering a "boy" or slave contest.


Every home should have one (hopefully a full length) Look at yourself before you step out into the public, and check yourself in the mirror in the dressing room, or bathroom at the contest site.


Contests should be fun for you, but do not let someone who knows nothing about leatherwear, tell you that you look good when you look all wrong!

You are not in the contest to make a fashion statement, and wind up looking ridiculous. Not everyone looks good in EVERYTHING!!!! LOOK SMART BY DRESSING THE PART


Everyone who enters a contest, hopes that they will win the sash. If you win, don't put the sash on over a T-shirt!!! Sashes are made to be worn at various occasions--NOT, every occasion. A medallion will do the trick for those other times that you are out. Have a nice leather band made to hang your medallion on if you choose. Or you can certainly have a vest made with your title on it.

This is preferred by most title holders.

Hopefully this information will assist those that wish to seek fame, and perhaps some that just need to know.

© 2014 - Fits Like a Glove (FLAG)