This is something I need help with, the part of me that loves cars always fights w/ the part of me that loves money. I make about 100k a year, and live on about 20k a year (in LA which is no easy feat), I drive a boring sensible 2002 car that will probably go forever and is very cheap to own. I'm not married and have no kids, and I LOVE cars, I REALLY want to have one nice vehicle, newer cars aren't overly interesting, and within a few years the body styles change so drastically something new looks like it's 10 years old in a few years....I'd rather spend 20-30k on a nice classic that I can enjoy, but I always think about how much more it will cost in repairs, gas, etc. What do I do??
I also had a guilt complex about our car until the wonderful people on this site suggested that I consider the cost of the car in our "entertainment/hobby" expense instead of transportation. That made a lot of sense. We basically only drive the car to cruise -ins and fund raisers and maybe short trips on weekends. Of course we already have the car so it is just maintenance, and insurance. We have a lot of fun with it and hang out with a great group of people at the cruise ins. In your case, if you don't go with the really popular classics you can find a nice car for that amount of money. I agree that the newer cars have no style at all. What kind of car are you considering?
That's kind of how I've tried to justify it, to some people a car is just a car, but I'm one of those people that think it's a piece of art, and REALLY enjoy driving. Some people talk about how much more difficult older cars are to drive, but I actually enjoy the effort it takes. I do appreciate how newer cars are more reliable, but it's a trade off, with reliability comes boredom. My car now has never let me down, and I love it for that, but I enjoy it about as much as I enjoy my refrigerator.
I live very simply and frugally and just dump all money over my core living expenses in to Vanguard, so this would be my only thing I'm enjoying spending my money on, other than savings for FIRE. Problem is in my head that purchase would delay FIRE somewhat, however I would be deny myself something I would enjoy forever. I have a garage only big enough for one car, and refuse to deal with street parking so I'd want something that I could use as a daily driver. In the past I owned a '72 VW Westy that I used as daily driver until I wrecked it, and I loved the vehicle more than anything I've ever owned since, it was not immaculate by any means, but it was such a joy to drive and own. If I were to go the classic route again I'm not sure what I would pick, I love the big boat American classic cars, but I also wouldn't be able to fit one in my garage, and they are probably less reliable than a smaller classic such as a Volvo or what not.
It's tough because part of me would love to just buy an awesome new car, but like I said, within a few years it is "old" looking and the fun is gone, whereas with a classic it always looks great because there is nothing else like it, so instead of spending 80k on a new "luxury" car, I'd rather spend much less on a great classic that I will love, and still have money for when things go wrong.