I once asked a couple, both well known as gardeners, what they wore on their feet when gardening, they seemed offended by the question and said ,rather tersely "What ever we're wearing at the time". I had a picture of them tripping through their bog garden in fluffy bedroom slippers and decided not to pursue the subject any further. Perhaps they thought that I was looking for a recommendation for a pair of over-priced "branded" wellingtons; but rather, I was hoping to find that they had a pair of shoes that though wear and familiarity had taken on the character of a much loved side-kick.
There are certainly many examples of these well-worn items, William Nicolson's painting od Miss Jekyll's Boots is almost as well known as his portrait of the lady gardener herself.
Miss Jekyll's Boots by William Nicolson.
More recently I found in Edwin Smith's beautiful photography book "Evocations of Place" a wonderful picture of Vita Sackville-West's boots. They looked very severe and probably took quite a bit of time to break in, but the photographer certainly saw them as an image worth preserving.
Vita Sackville -West's Boots photograph by Edwin Smith.
I've given up on gardening shoes with cleats, after finding myself several inches taller from the accumulated mud and gravel stuck to the bottom of the soles. For that reason own favourite is a pair of Geox that are easy to slip on and off and with a reasonably flat soles that don't collect debris on the bottoms.
My own well worn boots.