Clothes seem to me another area where society has gone rather crazy. Over the last five years I had three children so I was always either pregnant (and therefore not in clothes-buying mode...) or else whatever was in fashion was so awful that I just couldn't bear the thought of wearing any of these things. That has given me a totally new perspective on clothes and fashion. I also realised that it does not matter one bit whether I wear something something fashionable or new - as long as I feel comfortable in it, nobody takes much notice anyway.
So now, instead of buying new, I use second hand clothes. I have always worn many of my clothes for years and I make many things myself. My children wear mostly pre-loved clothes. My grand total expenditure for my own wardrobe this year was approximately $20.00 - and I am wearing perfectly normal clothes, nothing that would make me stand out as odd or different.
I wear my shoes until they fall apart. I find it is worthwhile investing in a good pair of shoes. My last pair of shoes I bought four years ago and they have lasted well until now.
My favourite spring jacket is about 20 years old but it is still doing a fine job and I see no need to replace it. I even have a lovely jumper that dates back to the early 1980s (it was hand-made by a friend of mine) which has just come back into fashion! The key is to buy things that will last longer than just one season, both in terms of style as well as quality, and to look after things, treat them kindly and keep them in good shape by fixing any damage as soon as it appears.