I used to own jags for several years mostly XJS's and loved them but I've had my LS for 5 years now and still love it. The wife always says it's and old man's car but admits its a great way to travel and is as quick as her Boxster! The only looks you have to worry about are inside when you're sitting in it - you can't drive and look at the outside at the same time (well except in shop windows!).
If you're worried about fuel my LS has avergaed about 25.5mpg over the last 100,000 miles.
I always bought Jags cause they were british and stopped when ford bought them, had an A8 - great car but not that comfortable (and you say you're not in the bracket for the latest model).
Why do I drive an old LS400 and not the newer LS430 because, in my opinion, the LS400 is still better to drive and all the improvements inside were for the passenger not the driver but an LS460 :D