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Top Tranny Tips: Shoes, Sandals & Boots

High Heels, Kinky Boots and Sexy Strappy Sandals

The Perfect TrannyIf there is one virtually universal constant that pervades probably 90% of the world's trannies, it's high heel shoes! It seems that all transvestites and cross-dressers fundamentally believe that wearing high heels is one sure fire way to make ourselves look and feel more feminine.
Women wear heels because they make the wearer look better, longer-legged, more sexy, and because men like them."
Christian Leboutin
Metropolitan Magazine
March 2012
There's no doubt that if worn properly and if you get a lot of practice in, the effect on your poise is to make you walk in a more female way, but that's probably not the reason that all girls wear them. At the end of the day, trannnies and women alike both know that a good pair of high-heels, whether boots, sandals, pumps or mules, just looks damned sexy. Not that this needs any proof but take a look around your average swanky hotel bar, upmarket night club or at a sophisticated soiree and see what the girls have glammed up their look with - you will be hard pushed to find anyone not wearing a knock-out pair of at least 4" heels. Heels add femininity and sexiness - it's probably as simple as that, as Christian Leboutin himself says (see box on the left).

What's in a name?

It may seem more than obvious to experienced high-heeled trannies, stiletto-wearing cross-dressers and to your typical shoe-loving woman, but novices to the whole shoe thing might not know what the different definitions of shoe type actually mean. So here, with apologies to those for whom this is like teaching your proverbial grandmother to suck eggs, is a tranny guide to the different types of shoes. As a picture speaks a thousand words, putting your mouse over any of the titles will bring up a picture of the shoe being described.
  • High Heels - Usually refers to shoes which have a heel height (from the floor to the top of the heel) of at least 3 inches (8cm) though there are some with lower heels that claim to fall into this category - it's a matter of judgement.
  • Kitten Heels - Shoes with heels which are not 'high heels' but are also not flat. Normally used to describe shoes with a 1 or 2 inch heel.
  • Ballet Heels - Ballet shoes (or ballet slippers) are usually very flat with lots of silk straps that you tie up your leg - as used by balled dancers. Ballet heels, on the other hand, are heels which are at least 7 inches high and force your foot to be virtually in-line with your leg. Very painful and meant only for fetish type situations and not for daily wear. They are almost impossible to walk in.
  • Stiletto - Named after an Italian knife, and implies that the heel of the shoe is very thin and narrow. Stilettos are notoriously difficult to walk in as you are effectively balancing on a nail all the time! Stiletto shoes is also a European term used to describe 'pumps' (see below).
  • Sandals - Shoes which usually comprise a series of straps rather than covering your foot solidly (hence 'strappy sandals').
  • Slingbacks - Shoes which have a strap which goes around the back of your foot/lower ankle and which are usually solid around your toes like a pump.
  • Pumps - An American term used to describe high heel (usually stiletto) shoes which completely cover your foot. Come in various shapes and designs, but pure pumps should be simple with no ankle-straps, peep-toes or anything else.
  • Court Shoes - The British term for pumps.
  • Peep-Toe - A shoe (usually a pump) with a hole at the front for your toe(s) to peep out. Fine if you have your toe-nails painted, otherwise a bit of a no-go. Can also have the effect of squeezing your toes together which can be mighty uncomfortable after a while.
  • T-Bar - Shoes which have a 'T' shaped strap across the top of the foot.
  • Platforms - Platforms have a built up sole to raise the overall height of the wearer above the ground without forcing the foot into painful and unnatural angles.
  • Ankle-Strap - A strap, usually fastened with a buckle, which goes around your ankle. Often found on pumps and sandals. Multiple ankle-straps are increasingly common. One of the claimed advantages of an ankle-strap is that it makes your legs look longer. Not sure about this but done well, they can be very fetching.
  • Mules - Usually high heel shoes (though can be kitten heel) which only have a strap that goes over the front of your foot to hold them on. A mule has no material or anything else that goes around the back of your foot, your ankle or your heel and thus gives no support and can be a devil to wear (although as any heel officionado will tell you, the devil wears Prada!)
  • Wedge - A shoe where the space between the heel and the sole is filled in such that there is a single solid piece between the two.
  • Espadrille - A strappy wedge type of shoe where the piece that forms the heel and sole is usually encased in string or rope. The uppers are often made of fabric.
  • Mary-Jane - A style of shoe based on a pump or court shoe which has a single strap across the front of the foot which usually is fastned with a buckle.
  • Boots - Oh, c'mon - you need me to describe boots? OK, boots are shoes which continue up your leg from your foot and cover, as a minimum, your ankle. Boots have different lengths ranging from 'ankle' (which go as far as your ankle), 'knee-high' (which usually stop just below the knee) and 'thigh-high' (which go all the way up your leg to your thigh). Boots can actually be very good for transvestites and cross-dressers as the additional support they give to your ankle can keep you from falling off your heels and tearing tendons and so on…
  • Kinky Boots - Not an official term, but refers to boots which either have a very high heel (and thus are verging on the side of fetish) or thigh boots. Generally the wearing of kinky boots will somehow impede the movement of the wearer and thus render them only able to do kinky, rather than day-to-day things!
  • Flip Flops - Also known as 'thongs' in Australia. These are flat soled shoes which usually have a pin which goes between your big toe and the next toe along which then connects to a 'V' shaped strap to hold it on. Called 'flip flop' because of the noise they make when you walk in them.
  • Flatties - Any shoe with no heel at all. Flatties are normally only worn by trannies when getting from place to place as they are comfortable but generally very unflattering.
That's a rather long and somewhat pointlessly comprehesive list together with a few tips on wearing them, so now onto something you might not know…


Buying Heels for Trannies

High HeelsFlat shoes might be more comfortable (especially if you've got to walk any distance in them) but they just don't look the same. So that out of the way, what's the reality of buying, wearing and walking in high heels for most trannies? Well let's first assume that you're hell bent on wearing high-heels, here are a few tips that should help you make it through the pitfalls that beset most first time cross-dressing stiletto wearers:
  1. There are lots of companies who supply ladies shoes (whether high-heeled or not) in larger sizes, however many of the larger sizes are designed specifically for 'men' and tend to be at the more fetish end of the shoe spectrum. Typical high-street shops stock shoes up to a UK Size 8 (US Size 10 - see the conversion chart below). A few UK high-street shops do stock shoes in Size 9 and these include Wallis, Next, New Look and Faith, however not all styles are available in these larger sizes. It's more normal to have to go to a specialist supplier, however this shouldn't mean paying through your nose: shop around - a good pair of stiletto pumps shouldn't cost more than about £40 (about US$60). Some retailers, knowing that such items are for a specialist transvestite market try to charge a lot more. Try Bananashoes who are a very reputable (and very tranny-friendly) UK supplier and come highly recommended or even better, visit the Trans-MISSION personal shopper and browse the sexy high heel shoes specially selected for trannies.
  2. 7 inch heelsBe sensible about just how high a heel you are capable of wearing. For most T*Girls, wearing a 3 inch heel is relatively straightforward, and even a 4 inch heel might not cause too many difficulties. Above this, the tendons and muscles in your ankle will be stretched into shapes they just aren't used to - you might even find you can't stretch your ankle this far (certainly to begin with) and you'll end up stooping forwards when walking (think 'Quasimodo') in order to fit into your crystal slippers! 5, 6, 7 and 8 inch heels are purely for the boudoir, unless you're an absolute expert. Platform shoes with high heels are less of a strain as the actual difference in height between the front and the rear of your foot is the height of the heel minus the height of the platform (watch out though, unless you're used to walking in stilts, or wore platforms in their heyday in the 1970's, you'll need practise in these too!)
  3. The Trans-MISSION guide to tranny shoe sizing below shows the conversion between UK, European and US shoe sizes. You will sometimes find that the size of shoes don't match the figures shown below. Shoes that are sold as UK Size 9 might be labelled '9/43' being a European Size 43, or might be a '9/42'. In the case of a 9/42 shoe - beware - it might be much closer to a UK Size 8 in reality. Also, different suppliers shoes will be slightly different sizes to each other - this can be a real bind as just because you're normally one size, doesn't mean you will be this size for all manufacturers (this is equally true of mens shoes as it is of ladies).
  4. When buying very high heels (4 inches and above), it's often recommended to add one to your normal 'male' shoe size to allow for the fact that when tilted at an angle, your foot will require more space than when it's lying flat, so the word is that if you're normally an 8, go for a 9. Sadly, this is a bit of a misnomer. Some manufacturers allow for this tilting when deciding what size to call a shoe, others don't and this makes it difficult to know what size you should buy. To play it safe, add a half-size on and see where that gets you. If you're normally a size 9 in male shoes, go for a 10 - you can always send it back.

Walking in High Heels

high heel cyclistThere are very few real problems with walking in high-heels once you get used to them, but as with all things, practice makes perfect. Don't go head over heels! Before you wear a pair of high-heels out for the first time, wear them around the house first. Not only will this let you get a feel for how difficult walking in them might be, but if they are really painful, it's best to discover this at home rather than whilst a half mile walk from your car on the way home from a night out trannying! The added benefit to wearing your strappy sandals at home first is that it can stretch them a little and shape them to your own feet and stretch your ankle too. I know of one girl who regularly sleeps in new high heel shoes to let this accustomisation happen whilst she's dozing (and I mean sleeps as opposed to any more energetic bedroom night time activities!)

Lastly, there are cross-dressers, transvesites and even 'everyday' men and women who are so wrapped up in the whole 'shoe-fetish' thing, that they insist on keeping their kinky boots on at all times, including whilst 'at it' in bed! Such actions are well outside the scope of this page however a note of caution if you're thinking of going in this direction - heels have a tendency to have sharp edges and can easily rip bed sheets and other delicate things... Oh, and as for using high heel shoes as sex toys, well I'll leave that to your imagination, suffice to say sharp edges could be very (very) painful!

Tranny Shoe Size Chart
UK¹US WomensEU/China²
3 35¼
6 35¾
4 36½
7 37
5 37¾
8 38½
6 39
9 39¾
7 40¼
10 41
8 10½ 41½
11 42¼
9 11½ 42¾
12 43½
10 12½ 44
10½ 13 44¾
11 13½ 45¼
11½ 14 46
12 14½ 46½
12½ 15 47¼
13 15½ 48


¹ UK Mens and Womens shoes use the same sizing hence a UK 9 mens shoe is the same size as a UK 9 female.
² Some conversions have Chinese sizes plus or minus 1 different from the EU size.
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