Gear is gear, and totally necessary. I'm thinking more of another graying lady I love dearly who hadn't updated her style in about 30 years? She was still wearing some cotton tops I'd worn in middle school and that she found practical and liked the the color of. She really enjoyed me playing stylist in her closet and a shopping trip after which her self-esteem for visual presentation (she's very confident in other areas) went up. She said she felt 'hip' while still feeling physically comfortable in her favorite colors and fabrics.
Before YLF I'd also gone a reaaally long time without questioning or exploring my style -- it was comfortable, and I felt like myself -- but I wasn't really recognizing that 'myself' had changed too over time. It was liberating and uplifting to embrace the changes.
For me it's great to celebrate ones eccentricity and uniqueness and the tried and true, but there is also a pleasure in living in time, in being part of a social moment--whether it's in media, in clothes, in food, in which discovery and change is constant.
I guess I think that it's not so much about chasing trends each season (although for me it's fun to explore the new possibilities while being mindful of time/money/consumption), but checking in at least once every 15 years to the details, because our bodies aren't the same, our hair isn't the same color or texture, what fit us psychologically like a glove in the past, might just be familiar, but not quite the best solution in the present moment.