Bijou, what a great question. It makes absolute sense that you'd focus on your beautiful dress collection as the essential area to keep pristine and up to date. I do think that the "joy per wear" factor can never be dismissed and those items or categories of item that tend to bring us joy will be easier for us to justify spending on.
"Trendy" used to have negative connotations to me, too -- but now that I stop to think about it, why? Because even as a 14 year old I was following the trends. Not buying into them willy nilly -- no way! But picking and choosing, you bet!
I think staying "current" or even "trendy" is a valuable style goal for those of us whose core style is classic. Without the "modern" classic can quickly look (and more important, feel) stodgy, boring, dull, and even uncomfortable at times.
My core style sensibility is extremely classic...with a bit of prep, a tiny bit of punk, a bit of retro. And I'm (ahem) part of the grey-haired well over 50 age group. I am in no way trying to deny my age, but neither do I want to appear less energetic and lively than I feel. So "trendy" has come to be a plus in my fashion vocabulary. Caro from Oz (forum member) always said she feels that following trends or being current has become even more important, rather than less important, to her as she ages. I'm with her.
Phew, that got long. Anyway -- I like to maintain currency especially with:
- Haircut (and colour).
- Denim (since I wear it so regularly).
- Footwear.
- One or two seasonal "must haves" assuming one or two of them speak to me. (If not, I let that go.)
My toppers, tops, dresses, accessories, and bags tend to be much more classic. I love a great collection of blazers and blazers, as much as denim, are a wardrobe essential for me -- but mine are mostly pretty standard in cut and style -- or at least, the ones I wear the most fall into that category. I
do love the drama of a colourful or patterned coat, but it's often in a fairly classic style. In fact, I'd say I purposely look for wardrobe longevity in most of my coats, blazers, and dresses -- with a space for a trendy wild card or two.