My feet are fussy, and wide. Personally I've always adored the look of pointy toe shoes, not only because they elongate my legs, but also my small yet wide feet. I find that not all pointy toes are created equal -- not all are terribly uncomfortable and downright torture devices. You just have to try a lot of them on, to find the ones that work.
If it is a heel, the most important element seems to be the slope. Does it throw my weight backward on to the heel, or forward on to my toes? Not only will forward slope cause my foot to slide forward jamming toes into the pointy part, but also it puts all the pressure on the metatarsals which then spread while also being squashed into the toe box. This is a recipe for lots of pain, and even injury! If the slope is right then this doesn't happen and that applies no matter what the toe shape -- or even heel height (within limits -- you probably won't find me in 5 inch heels ever).
The second element is where the pointy part starts. It should start beyond the widest part of your foot -- beyond the metatarsals. This means a proper pointy toed shoe is going to be longer than your other shoes. You can't necessarily achieve this with sizing up either, though it's worth a try. Usually for me this doesn't work because the shoe is then too big all over and my toes just want to slide too far into the toe box, or the shoe just won't stay on.
I don't know if anyone remembers when extreme pointy toes were all the rage? I loved that trend and embraced it wholeheartedly (I felt like a little elf). I found plenty of comfortable options back then. It's all in how the shoe is designed.
My current favorite booties are pointy toed and they are the most comfortable heel in my closet right now. I have round toed heels that aren't nearly as comfortable. So, lesson is -- it's not the shape of the toe. It's the shape of the rest of the shoe.