This question about dyeing hair into unnatural colour using medieval technologies was closed as a duplicate of this question asking about dyeing red hair into a natural colour in a similar setting. However, these questions require very different answers due to several considerations explained below.
Unnatural hair colour is a two-step process: Bleach, then dye
Natural colour does not require bleaching. There is a wide range of natural hair colours that can be easily achieved without extreme chemical processing. For the natural hair colour question, the easiest and least damaging option would be dyeing hair darker and changing its shade into brown.
Unnatural colour requires bleaching in all cases, except when the base colour (the natural hair) is very light blond. Dark hair is very hard to dye and unnatural colours like blue, yellow, green, bright red, orange, and so on are impossible to achieve without bleaching. This is precisely the reason why the majority of sheep raised for wool is white: It increases dyeing options. Wool from non-white sheep is rarely dyed and is often spun as it is.
Even highly pigmented dyes do not produce unnatural colour results when applied to dark hair (medium brown and darker), they only result in a change of hue. The darker the base the less noticeable this change will be.
Limitations of medieval hair dyeing options
Medieval hair bleaching options were very limited and did not produce results similar to hair bleaches of today. The most popular bleaches were lye soap and ammonia. In addition to these, people would expose hair to the sun to lighten it (sometimes using lemon juice and similar remedies to increase the bleaching effect). All of these approaches have 2 things in common: 1) They are not capable of colour lifting to the same degree as modern bleaches (it is impossible to achieve very light shades unless the hair is originally light); 2) they seriously damage the hair (the hair becomes prone to breakage; overprocessing can even make hair so fragile that it breaks at touch).
Many colour dyes, while probably not highly toxic, are still damaging for the hair. For example, woad dye (blue plant-based dye) is known to damage protein-based fibres and should be used with great care. It is possible that some (if not all) formulations of woad dye cannot be used on bleached hair at all since it would lead to extreme damage and full loss of hair length due to breakage.
If we consider these 2 points, the answers to the unnatural hair colour question are limited to dyes that:
- are available in the Middle Ages;
- are non-lethal to humans (toxic dyes where toxicity accumulates over time are fine since lead makeup was a thing for millennia);
- can be safely used on bleached hair (this is probably the greatest limitation);
- produce unnatural colours when applied to the yellow-orange medium blond base (this would be the average result for bleaching in medieval Europe).
This is a different set of dyes compared to the natural hair colour question which looks for the following:
- are available in the Middle Ages;
- are non-lethal to humans (toxic dyes where toxicity accumulates over time are fine since lead makeup was a thing for millennia);
- reduce or mask red pigment in the original hair;
- produce natural hair colour when applied to a red base.
Notes:
This is not my question
This is not a perfect question, but let's stay focused on the duplicate issue.
Please note that the accepted answer is not correct: Not all dyes that can be used on white wool can be used on human hair.