LJP, I'm still learning this too. Clothes I own and have loved in the past don't fit the more rounded body I have today, even though in some cases I can button or zip. Or, as you say, they look too tiny or fitted and don't look current. I'm appreciative of the changes to more oversized and fluid fits available now.

Interesting comments. I have two leather motos. They were a bit tight but after a health issue and a big drop in weight, they are now loose—so I am glad I kept them. You never know.

I added a Moto toward the tail-end of the period where they were trending. Fits were already skewing more relaxed at that point (maybe 2018-19ish?) so I opted for my larger size and still find myself wearing it a few times a year. The combo of warm brown with silver hardware is so hard to find that I don't think I'll let go of it til it wears out. The thing I'm really not reaching for is my much-more-fitted denim jacket. Hanging onto it though because, again, silver hardware!