I've been wondering about this, looking for some tall boots. I wear skirts, usually longish, so am considering some, but they would have to last me a long time, and not have any trendy quirks.
A timeless boot, to me, doesn't have a stand-out style that ties in with a current trend. So perhaps a riding style boot?
I also have a long tweed coat that feels timeless, kind of Withnail and I, so I seem to like things that 'feel' expensive but are a bit boho, and it fits the bill nicely!
But on the other hand, would anyone say these boots (pictured) are timeless? The cleated chunky sole is having a moment, so i wonder how quickly i would tire of them (they are from celtic&co), and for £199, they'd have to pay their way...
What does it mean to you? I am presuming we are all different. Some so-called timeless items do tend to date, no matter how many Parisian experts tell us they won't!