What I am learning in my retirement, which does not have universal application, is that it is not so much about frugal as to how much I intend to use/enjoy what I choose to spend on.
For example, my Amazon wish list (where I put things that I'd like to have, or just think might be interesting) currently has about 30 items. Buying all of them at one fell swoop would be around $1200. Spending that is not a big deal. But my thinking becomes "fwhen will I have the time to effectively use/work with all of those items?" So it becomes more of "I'll get something when I have the time to work on/use it".
I decided to play with drones, so I bought one about a year ago... and even with retirement, have flown it twice. The cost does not matter to me, but getting the time to play with it does. And I have so many things I like to do these days...
But I agree with the preceding comments about working on it a category at a time:
- Purchased a new laptop - in the past, would have seen what I could get in the $300 range. This time, since I wanted to use it for various programming/open source projects, got one with lots of memory and storage for $800 (I was prepared to spend over $1000 when I came across what I felt was a good deal for the equivalent)
- We are planning a trip to Asia to visit relatives in the next several months. Now I concern myself more with the timing of when it is best for everyone, vs. the cheapest time for us to fly there. As well as looking at tickets above economy class.
- Since I was a kid through my 50s I probably have 1 or 2 pairs of sneakers at a time - one high top pair, one low top pair. Now I am up to seven concurrent pairs - 2 for walking, 3 for workouts/cross training, 1 for basketball, 1 "slip on" for the house (better than slippers).