I think the 986 can still look fresh depending on a few things- I've had people come to my house to repair things and they think my 986 is brand new until I told em it I've had it for 15 yrs. The things that stand out the most to date the car I think are the plastic rear window, small 16 or 17" standard factory wheels and amber lights. Adding side skirting I also think helps make the car look more aggressive and modern. Put on the 03 factory top with glass, 18" wheels, litronic headlamps and clear lighting all around, and skirts, and I think it looks less dated against the 987 and even newer models. Oh, and paint those bumperettes! That being said, if I were to spend more money, I'd forgo the new 981, and get a preowned 997 cab for a different experience.
When I first got her:
And later: