This is a very good question, Shannon. There is a LOT of dated jewelry out there. I am vigorous when I clear out the jewelry boxes of my clients.
There is also a LOT of timeless jewelry. I have clients who wear the same fine jewelry pieces day in and day out and they are hip and modern. For example, client and good friend Phoebe wears a classic tennis bracelet every day. It's part of her style and matches her wedding ring. It never comes off because she loves bling. Client Bei-Jing wears huge diamond stud earrings that never come off either. She also loves bling
Client Meredith wears arty "conversational" necklaces every day - like a "teapot" pendant because she loves tea. Also part of her look. Not dated.
I have clients in their 60's and 70's who wear the best vintage costume jewelry I have ever seen. Not dated.
My late Mum and Granny only wore "bulky yet refined" real jewelry. Lots of gold and gems like emeralds, rubies, garnets and pearls. I have pieces of theirs from the '50s, '60's, 70's, 80's, and 90's. None of it looks dated to my eye. I wear it very occasionally.
Simple pearl and diamond pieces - never look dated.
As for *wearing* jewelry, I personally do not wear it 95% of the time because I have a minimal modern style. I want my hair, specs and clothes to make the statement, and not the jewelry. But it is not at all dated to wear jewelry that is either timeless or on trend.
Speaking of on trend, arm candy and rings are definitely more on trend than necklaces at the moment.
I hope that makes sense!