I spend an awful lot on clothes, even from my own perspective. I am not concerned with price as long as I like something and it has value which can either be lasting or ephemeral. I take care of my things and they last a long time, plus im quite clean so my things dont degrade, so price is relative. However, Im not looking to throw money away on someone purposefully overcharging, and there is a price limit. That said, I have my favorites and I stick with them. However, i am open to new ideas, mainly in accesories/furnishings. I might try some siviglia shirts (forgive me Adam!) and I like the Marinella ties. Im going to try one of those Mario Talirico umbrellas Marc linked but I wished theyd heard of black fabric.
Which may be why I like the Neopolitan aesthetic, from necessity they have combined old money restraint with an tactile love of beauty and made every single inch of what they wear interesting and elegant. All with a mediterranean sense of sociability. A very good blend.
Unless you'll be in the rain for long stretches at a time, cotton should be fine.
A silk canopy for an umbrella makes for a lovely sound when the raindrops hit it.
Shoes
As the shoes can last much longer than clothes and involve confort i think it is the area in which one shouldn't try to save.
Therefore I would not buy shoes which have a tag value under 500 euros and i could spend till 800 euros for a good pair.
Ties
There is no problem of size so it is very easy to find bargains, ties at 80% off. So i think i would spend the least on a tie, not more than 50 euros.
I think a good wardrobe is the most important purchase in life. Before i do not have it, i only spend in clothes.