I like the shape of the boot and the toe, but not the heel, not so much the height but the clunkyness.
I think flat boots are always not "in fashion" as there will always be huge swathes of Doc, Solvair, Dubarry boot wearers around because (a) it's actually necessary for their lifestyles, hobbies and jobs or (b) that's just their thing. So wearing flat boots even if you're not a police person, jockey, soldier, workman, farmer etc is Ok because there's simply so many flat boots always in circulation.
Wearers of flat boots (and indeed floral dresses) will from time to time be fashionable but it doesn't matter when they aren't.