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Shoe Sizing in a Crossdressing Context

Updated on October 27, 2019

M&S insolia flex ballerina pumps

Rethinking your shoe size when trying unfamiliar footwear

Online shopping is growing but shoes are a difficult proposition for retailers, which is why sensible people prefer to buy theirs from shops where they can try them on first before making a commitment. There are several shoe sizing standards including US sizing for men and women, UK sizing that also works similarly, but are more uniform (seems to include both sexes) and best of all EUR sizing that applies to feet sizes regardless of gender. The Japanese take foot length into account sizing shoes in cm. Online retailers are wise to also offer width standards from D to E, EE and EEE. Nike are now designing virtual reality algorithms to their apps so they can sell shoes that should be a guaranteed fit.

In order to placate the online market, most professional companies offer quibble free returns to customers who buy shoes based on size descriptions and appearance online, but may be very disappointed by the actual pair, even if they like the design. Shoes that don’t fit are only good to be returned or sold on.

Online shoe shopping may be preferable for people who wish to buy shoes experimentally for two main reasons. Second hand shoes are often a quarter of the price of new shoes and may still be relatively mint when sold on an online platform, besides, if you wish to try shoes of the opposite sex, it may be a bit embarrassing to be seen in a shop prancing about in them.

Women’s shoes predominate in being slip on slip off styles rather than lace up. This applies to heeled shoes and sling-backs or flat court shoes or pumps in particular. Such shoes are more difficult to get a fit for without trying on first. They employ two design aspects to fit – they mould to the shape of the foot, thereby clinging to it – especially for flat shoes. With even kitten heels, the rear elevation will also provide part of a fit as gravity from weight forces the front part of the foot into the shoe, helping to keep the shoe in place. Care should be taken not to distort the toes in this process, but sadly, high heels often have this effect. As slip on shoes, though very elegant can’t always be expected to fit, and a larger size may be more comfortable, straps and buckles will solve these problems. You won’t however be able to wantonly “kick off your heels”.

There is one further way in which slip on shoes fit: as the foot releases moisture, the shoes naturally stick to the foot. Technologies like “insolia-flexTM” (as used by British Marks and Spencer) may generate suction between the shoe and the foot from the sole, to stop the shoe from detaching too easily. In order to provide this sort of clinginess, women’s shoes are often padded with spongy, smooth linings that are soft, supportive and slightly sticky.

Men’s designs and other general more closed shoes including boots or lace ups will rely on the laces or a narrow mouth at the ankle area, so the foot fit may be quite lose in the shoe. This looseness within the shoe may be comfortable and the shoe may always be kept in place by the constrictions at the upper shoe and ankle.

As a generality, if you are accustomed to a certain size in men’s shoes and wish to try women’s footwear of a slip-on nature, you may, actually need to consider going for a reduced size. You may realise your shoe size does not reflect your foot size, as men’s shoes fit because of constrictions at the ankle or laces, in a typically loser shoe, than the tighter feminine styles. This partly explains differences in men and women’s sizing as they reflect shoe designs and fitting mechanisms rather than foot size.

Using the EUR standard, I’ve been trying several shoes and have found that the smallest women’s shoe that will fit will be up to two sizes lower than the assumed male size. Sandals in particular will have a flexible fit due to their straps. You may be surprised that smaller ones fit better.

A man with UK size 10 shoes may in fact fit a woman’s size 7 shoe as long as there is some measure of wide fitting (all feet will fit larger sizes, that would need to be managed using shoe inserts or straps). Size 10 slip on women’s shoes may prove too large and this could be very disappointing. Wide fit may be more important given larger feet are often larger by width than by length and most shoe sizes only refer to foot length. Women who wish to wear men’s shoes will find an easier fit as systems such as lacing or boots will allow more flexibility.

There is no such thing as a correct size except “usually”. Only a correct fit. Many women’s feet swell during pregnancy and they may need larger shoes when pregnant or before they lose weight than postnatally or after a diet that worked. Adult shoe sizes will vary in a different context to the growing feet of youngsters and fit will depend on a particular pair of shoes.

The best shoes you can buy will be a custom fit – indeed, each shoe may need to a be a slightly different size given one foot may be stronger or more normal than another that is for example developing a bunion, even incipiently. Such custom shoes may prove very costly and would mostly be accessible only those who can afford them. In order to DIY custom fit, If you can afford them, you could buy two pairs of the same shoes, perhaps a half a size apart so you can pick say a one size of one pair for one foot, and that size and a half for the other foot. You could still get rid of the remaining odd pair to a charity shop as the difference in fit may not be noticeable.

Back to the joy of online shopping and getting good, used pairs of shoes that may only cost slightly more than a price of a coffee so you can find the perfect ones for your collection, at the risk of having to dispose the ones that don’t work. Many people disdain used shoes, but they may offer styles you will never encounter otherwise at a price that’s right.

As for using ice expansion to enlarge tight shoes, or a hair-dryer while wearing them in socks (check online) - good luck. I’ve made larger, slip on women’s shoes fit by adding straps bought online that I had sewn on and coloured to match the shoes.

It’s a shame that the range of men’s shoes don’t cater for the breathability offered by women’s shoes rendering men easier victims of athlete’s foot and other fungal conditions from feet that are often not adequately dry or open to air circulation. The T-bar or Mary Jane strap was a feature in male shoes before the 1950s in otherwise minimal uppers, but designers have eliminated these straps from male shoes as a rule. It is probably time to create new men’s styles with opportunities for straps as these are far more breathable. There is, in any case a fad to avoid shoes altogether on a short-term basis or in warmer weather as this can be very good for the feet, earthing them in more than one sense of the word.

SUMMARY: Women’s shoes often cling to the form of the foot. A tight snug shoe may feel better than a larger one that comes off. Consider getting a shoe a half or whole size below your regular size for “closed” shoes, especially if buying sandals with adjustable fit that could be a smaller than you’re used to.



A shoe sizing chart. It’s useful to look at more than one.

Remember to take width into account.  UK size 7 can mean EU40-41, there’s inconsistency.
Remember to take width into account. UK size 7 can mean EU40-41, there’s inconsistency.

An answer from Meghan Munro, Quora on shoe sizing.

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