This is interesting, Carla. Like you, my style is quite classic but I do enjoy embracing *some* trends (the ones that appeal to me and suit me) because that is what helps keep fashion fun for me! I tend to agree with you that the secret to doing so in what we might call an ethical or sustainable way is:
1. Jump on the trend early. As you said. (Like Angie, I tend to do this with bottoms, if I can find a fit, because trendy bottoms make me happy. Recent examples would be cropped wider legs -- I had a pair four years ago! Ended up retiring for wear and replacing this year.)
Another trend I bought into early was higher shaft booties. I'm still wearing some of these early purchases and others I've worn out and upgraded/ replaced with similar models. For me, a higher shaft has proved practical so I won't be getting rid of them until they are worn out, trend or no. Even if we return to full length pants next year, I'll wear my higher shafts. The shaft will just be more hidden. Not a problem for me.
2. Ensure the trend is really *you* and not something you'll tire of easily. For me, and probably also for you, stripes fall into that category. Mariner striped tops were really hot for quite a while there. I bought in early and bought in hard and I am still wearing these (or their replacements) because Mariner stripes will always be "me" whether they are currently trendy or not! I definitely wear these out.
3. Again, your point: Buy conservatively if you are unsure or it's a wild card.
My example: A bell sleeved top. I loved, loved, loved, loved the colour...and wanted to try a bell sleeve. But I suspected it wouldn't work for me, and I was right. Too loosy goosy/ hard to layer / in the way of things I wanted to do. Sooo....that is an example of a trend I did indeed pass along, due to feeling "not okay" in it. (Not "dated" but just not myself.) Still, I passed it along with almost no wear, while it was still "trendy" (and thus attractive to someone else) and in good condition. And I didn't buy ten or twelve of these so it was an experiment as opposed to a waste. (Or at least that's how I see it.)
However -- I later found a good way to incorporate the trend -- for me -- and now, even though the trend is officially over I am happily still wearing this -- in the form of a structured jacket bought inexpensively on consignment vs. as a top. Bingo. (Items in Finds).
4. Buy as accessories. I like animal print but only in small doses. So my animal print purchases are footwear, scarf, belt. Ditto for the "western" trend last year. These will have longevity for me. A scarf or belt can be put in a holding zone for the next time the trend surfaces. In my case, most footwear gets worn out before the trend ends, because I walk so much. So it's not a worry.
5. If destined to be lesser-worn due to level of dressiness or casualness (or climate related reason) buy in your key neutral. You can get more wear from it during peak trend period. And after, it will blend seamlessly and less glaringly into your closet so you can continue wearing it past peak season if you wish. My example: paper bag waist midi.