If there's a demand, I'll write a separate guide to men's shoes for readers assigned female at birth, but that's a less complex subject and most of the queries about shoes here are from members assigned male at birth.
On the face of it, shoes are nowhere near as complicated as say, bra sizes, but even so, some common sizing systems have different numbers for the same size of shoe depending on whether it is a female one, or a male one. So I take a UK 7 in men's ranges, a 6½ in women's, a 40 EU shoe in either sex, a 7½ in US men's shoes and a 9½ in US women's.
Which means your first move should be to find a shoe conversion chart and work your size out.
Welcome to challenge number one, which is men commonly have larger feet than women. Until relatively recently many women's ranges went no larger than my size, but nowadays it is common for them to run at least two full sizes larger and some ranges extend to a 13 (aka 15½ in the States.) Or more. Better nutrition in childhood means each generation of women is taller than the preceding one and has bigger feet.
So the good news is that in most cases you should be able to find women's shoes to fit and the best news is that makers are appearing that specialise in larger sizes.
Fit matters more
Once you have found your size, the not so good news is width matters in shoes, but you will know if you have broad or narrow feet. The catch is that most women's shoes are designed to fit more snugly than men's, so fit can be critical.
Pikolinos are one of my favourite shoemakers because their products are so beautifully made and such high quality, but even so, I've had identical pairs of calf high boots from them in the same size, one pair of which fits while the other does not. The pair that fit are a tiny bit slacker in a critical place and fit like gloves and can be worn all day, while the pair that don't fit are hard to get on and uncomfortable after five minutes. There is no visible difference between the two pairs.
One reason why fit is more critical is because many women's shoes are stripped back to the minimum structure necessary to hold a foot in place. They are fashion items and the mantra of fashion is 'no gain without pain'. You can live a lifetime as a man and be unaware of this, because masculine scripts include one that women's fashion is not to be inquired about.
The stripped back chassis class of women's shoes means some only stay on because they fit tightly and will become uncomfortable after a few hours wear. I'm introducing this idea not because I agree with it, but because it is how it is. This is particularly so with heels, some of which will fit you well over a bare foot, yet become precarious if hose is worn or vice versa.
Staying with the subject of fit, I usually take an EU 40 with flats, but commonly find a 39 (that's half a size down in most sizing systems) is better with heels of more than an inch. In some cases a 38 will be a more comfortable fit. Every woman I have asked finds the same thing applies to her and it is something to do with the increasing angle of the foot with higher heels.
I've mentioned heels sometimes fit less well with tights, stockings or pop socks (hose in the US). But there will be shoes you buy for colder weather where you want something on your legs and others you will only wear with socks. So I have shoes which only fit when I'm wearing socks and others which wear best with stockings. Welcome to why women own more pairs of shoes than men.
Learning to walk again
Women's shoes can bring another right of passage, which is learning how to walk in them. Flats and sneakers are simple, but even wedges can be problematic, as can any heel over about an inch high the first time you wear them. The best advice I have here is, 'Start low and build up as you learn to balance.'
The second best advice I have is, 'If you wear heels out, watch for gratings and cracks in the footpath, because if you don't you'll regret it.'
Wearing heels tips your entire foot forward, altering your posture, never mind the way you walk. The posture alteration is part of the magic or the curse of heels depending on how you are minded to think of it, making your legs look longer and your ass more prominent, not to mention highlighting the curve in your back. By forcing your entire body out of its comfort zone, heels change everything from your gait to your mood.
The higher a heel, regardless of how thick it may be, the more difficult it is to walk in, because you have to sway your hips to lift and place your foot. No longer is it a matter of swinging your leg forward after bringing it just clear of the ground, because your ankle is closer to fully extended, which in turn limits how much you can flex your knee. All of this conspires to restrict the rolling your foot on landing - getting around this limitation takes some learning.
Ambition versus adhesion
Heels can bring another issue, because apart from altering the mechanics of how you walk, the thinner a heel is, the less contact you have with the ground. Most surfaces offer enough friction this does not matter, but you'll learn that some floor tiles offer low adhesion, while wet marble can be thrilling. Some wood floors and boat decks are incompatible with stilettos, so depending on the company you keep, learn to assess your environment's capacity for taking damage.
Heels can cause you damage too. One thing you do not want to do is 'fall off' a high heel because you can end up with some classy ankle injuries thanks to the leverage. So if you want to start wearing heels, take your time, wearing them inside and around your home, walking on a variety of surfaces until you have confidence in them.
You thought it ended with the shoe?
Another thing you should know about women's shoes is they go better with some clothes than others. Which means I have skinny jeans to wear with calf high boots, bootcut jeans to wear with ankle highs, longer jeans to wear with heels, shorter jeans to wear with flats and different coloured jeans to wear with different colours of shoe. You can see where this is leading, because the same issues arise with leggings, skirts and dresses...
You have been warned, but reading this won't stop you anymore than it did me.
