Hi
Hairstylist jumping in to give a little advice. First of all, I want to say that I know where your at, I've been every colour in the spectrum and many unnatural ones as well, I am also very familiar with Henna. As a natural blonde that can't stand her natural colour, I am doomed to colour for life.
I think the colour you've achieved with Henna is stunning. It is such a nice shade and SO shiny.
You would be able to get some of the red tone covered up with a brown henna, but the red would still show through very obviously. I know this because I've done it many times. Sometimes I long for the red shade, and other times I just want it GONE. The only thing I've found that can cover it up mostly is a brass free brown chemical colour. For this, I always use Natural Instincts "Brass Free" collection, but I must warn, in order to really cover the red you'll have to go darker than your natural shade, so you'd still have the root issue to deal with.
I took a look at your pics, and I really do love the henna red on you, but if you really want a change you're either going to have to go quite a bit darker, or deal with the red tint that will show through no matter which method of colouring you choose.
As for cutting, I can see why you're frustrated. As Spidermom commented, perhaps getting mini trims often could be an option for you. For this to work without you losing too much of your length and still gaining some, it would be helpful to know how much length you grow a month. I will go with the standard 1/2 inch per month for my example. Say your getting 1/2 in per month of growth. To get rid of some of the layering, especially the much longer parts in the middle you could have 1/4 in cut off per month and still be getting some length while eliminating some of the layering. It would of course be a long process, but with a goal of classic, you're in it for the long run anyway.
I think this type of mini trimming would help you reach your goals sooner, rather than waiting for it to grow to a length where you'd be comfortable with a big chop to even out the layers.
Good Luck!!
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