Festool power tools. Ridiculous money, especially for a gentleman amateur like myself, but once you buy the first one it's very hard to settle for Bosch Blue afterwards even at half the price. And Bosch Blue itself is pro grade.
Hilleberg tent. Again buttock clenching price and I only bought mine after two years of dithering. Now got two in different sizes.
Leitz binoculars (or zeiss for that matter) - a lot of money but the Krauts are still bloody good at optics. My full size leitz bins were off fleabay so merely very expensive rather than bonkers expensive. Still suberb though.
Crockett and Jones shoes. Ok they're not quite twice as good as top end Loakes but they are very nice. Most of mine have been 2nds so not quite as ruinous, but still not cheap.
By was of contrast my (excellent) car was £2.5k 7 years ago, so I'm all for good value, but am prepared, and by good fortune, able to pay for nice stuff where I feel it's justified