I've bought shoes in the UK from a number of different online sources with varying levels of success but over time I've found a few reliable locations where I'm generally happy with the results.
Bananashoes came under new management in November 2018 and have a new website which is a big improvement on the old version. They stock a variety of styles from the 'Pleaser' range. I find their shoes to be affordable, generally comfortable and I've bought the same pair of shoes from them 3 times because they are elegant but can also cope with a full night of dancing.
Amazon is home to a number of retailers of larger shoe sizes such as 'Onlymaker'. I have only bought one pair from Onlymaker but they were fine although on the small size.
Shopping in store
Trying on a pair of shoes in store can be daunting but it's a good way to get a feel for different styles, shapes and sizes.
I have been to one store in person which is Long Tall Sally. The staff there are very friendly and engaging and have been very supportive. As a brand, the shoes in Long Tall Sally tend towards the comfortable rather than the glamorous.
To date, I haven't found any high street store that stocks larger sizes (e.g. UK size 10+) with high heel styles. If you check Evans or other brands you are likely to find nothing much higher than a 1-2" heel in a size 9-10+.
I found shoe sizing to be a nightmare when I first started out in cross-dressing. Not only are shoes every bit as varied in sizing as clothes, they have the added potential to cause you significant pain and discomfort.
As a simple starting point, you should generally be able to use your male shoe measurement for women's shoes but we tend to have broader feet which can make sizing difficult.
Like anything else there will be an element of trial and error involved with online shopping, if you can get to a store that stocks larger sizes then so much the better.
I've had wildly different levels of success with certain styles of shoes and for me there is a key distinction between shoes for photos and shoes for walking in.
In photos you can pretty much wear any shoe you like, no matter how uncomfortable or difficult it is. When you see a woman wearing impossibly elegant shoes in a photoshoot it's tempting to rush straight out and buy them but if your intent is to go out any have fun, I would recommend a simple rule to start.
If I am walking or dancing, I will typically only wear shoes with a strap or boots and not much above a 4" heel. While I find court shoes very elegant, they have a tendancy to either slip off my feet or they cut up the back of my foot. If your feet are daintier than mine you are less likely to have these issues. However, once you find a comfortable pair, look after them!
Wear them in!
Walking in Heels
Walking in heels is a difficult thing to learn to do, there's a fairly high learning curve which can prove challenging. As always, the key tip is to practice!
I appreciate that many of us don't get the chance to do this as often as we would like but any opportunity is worth taking. Slip on a pair of heels (3" or less) and practice that hip wiggle!
The more you practice the more comfortable and confident you will be and this will show in your posture. I recommend practicing stairs as a particular art. Try turning your feet at a 45 degree angle and descending slightly sideways.
I've spent my whole life breaking in new male shoes while wearing socks but for some reason it never occurred to me to do the same with heels!
Taking the time to break in a new pair of heels with a pair of socks on can make all the difference for your first night out. The socks will protect your feet from rubbing and make a huge difference.
If I possibly can I will try to get in a good 5-8 hours on carpet at home before I wear a new pair of shoes out in tights or bare legs for the first time.
My Shoe Gallery
You can click on each photo in the gallery below to see the name and size of each shoe as well as the website I bought them through. You may even notice a trend :)