They're all gorgeous, but obviously the Reiss boots are best value for money. I'm 63 and wear elegant suede stiletto boots (ankle and knee-length) all winter (I prefer a slightly more almond-shaped toe, but some of my pairs are a bit more pointed). Like you, my days of wearing 4" (10cm) heels are long gone, but 8.5cm are perfectly comfortable (I went shopping all day in my navy suede Boden boots yesterday, which have a 8.5cm heel, with no problems at all). Personally, I'd try the Reiss first - if they're too big you can send them back, but if they fit well you've got a lovely pair of boots for a "bargain" price. If money's no object, the Jimmy Choo's get my vote.