Highlanders only go for around $40-50K, so most people won't think you're rich.
I bought a new 2006 LX-470 in my mid 30's and the new 2020 Land Cruiser in my early 50's. Between those, I had a 2008 Highlander, 2014 Range Rover, 2014 G550, 2016 G550, and 2017 G63 (all new), all of those vehicles prior to the current Land Cruiser held their values pretty well, but I'm hoping that I have the urge to get something new out of my system for a while now. I only owned the 2014 Range Rover for maybe 6 months - I should have gone with the G550 that I knew I really wanted, but the adjustable suspension height on the Range Rover seemed like a big plus for my short, elderly mom. As it turns out, the G550's running boards worked out fine for her. Range Rovers were so hard to get at that point that I pretty much got 100% of my money back trading it in at the Mercedes dealer. The Range Rover had so many issues even in only 6 months of ownership; what a huge disappointment that thing was.