The thing I say to people contemplating their first pair of shoes is that all they need to do is go on your feet and last long enough for you to make your second pair. It doesn’t matter if they’ve got things wrong with them. A pair of period shoes that didn’t quite come out right is still far better than wearing modern shoes with medieval clothing, and wearing the shoes is really the only way to find out how well they fit and hold up in use. If you make a pair and the second one works out much better than the first then you can always remake the first one. Making three shoes and getting two really good ones still beats making two full pairs.
This is one of my first pair of shoes, taken before I dyed them black. They were made from chrome-tanned upholstery leather, sewn up with waxed polyester thread with a lapped side seam. The heel came out all wrong, and there wasn’t much period about them, other than the vague shape and the fact that they were turned but I was, and still am, pretty proud of those for a first pair of shoes.
By the time you make your second or third pair you will be getting good enough at it to have something that will last a good long time. The second pair of shoes I made lasted me at events for 3 years. They were a bit crap, didn’t fit terribly well and as you can see from the pictures of them in a previous post, I really should have replaced them about a year and a half before I did, but I made them out of good materials and they did Ok. I advise starting on your next pair before your current ones are completely unwearable. Having to rush to finish a pair for the next event you’re going to is both stressful and likely to result in mistakes. It’s also true that if you come back to shoemaking after a long break of no practice you’ll have to relearn things, and the lessons of the previous pair won’t be as fresh in your mind.
Please don’t let all this put you off though. There is nothing to say that if you are careful and do a bit of research into what makes a good shoe before you start out, that your very first pair can’t be perfectly good shoes. Having someone who can help in person is a huge help, so find out who else in your group makes shoes and see if they will show you. It’s much easier to pick up the basic techniques when you can see them being done than it is just from words and pictures.
The most important thing is not to get put of when things don’t go according to plan. It can be frustrating as hell to put hours of work into something and have it not come out right, but if you can sit down and think about what went wrong — get a notebook and write it down — then you can learn from your mistakes so that you don’t make them again.