I think a lot of it too is understanding your body/body type. You can be well dressed at any body type but a lot of times older guys 40+ may have put on a few or really have fat in places they normally haven't and yet they either dress like it's still 2000, or try too hard and look like the old dude at the club. Neither is appealing. As I got older, I may have elements from my earlier days (like old school hip-hop t-shirts and Adidas sneaks but I'll things like the Jeans modern, but with all that, I but mostly off sales and clearance, and I rarely spend more than $40 on a pair of sneakers or casual shoes.