I am late 60s and replacing my wardrobe after significant weight loss. Now, I know both bootleg and leggings are flattering on me but because of my age I feel it looks like I haven't updated my look since the 80s/90s (leggings) or 00s (bootlegs). (Don't even get me started on tiered, Indian print maxi skirts since I remember the 70s very clearly - I hear these are making a comeback in certain quarters.) So my AIBU is:
YABU - wear what flatters you
YANBU - you have to be aware of both your age and what flatters you when it comes to re-cycled fashion trends.