Over the last 30 plus years I have tried countless pairs of (mainly black) boots for soldiering, Plodding, hunting and who knows what else. A lot in UK and now in NZ.
The ONLY rule is they must fit - so try before you buy, which can be a pain with interweb purchases.
Some personal opinions
Army DMS ankle boots - No, just OK for a work boot
Army light weight assault boot - originally marketed as the Britton boot in early 90s - not bad, and if available pretty cheap I think
Lundhags - pricey, boxy feel but a really good simple boot - good for everything but a hot dry summer for days on end. Would be good for Glastobury.
Danners - Gore tex etc - remember a very cold wet exercise when my feet NEVER dried out. Good comfy boots, but my Acadias (?) fitted fine without an insole, but the lining under the foot started to shift and ridge under the ball of my foot. Got my money back.
All leather/commando sole hill boots - good, but at the heavier end of the spectrum
Brasher - had the really light leather/gore tex one - bloody good actually
Altberg - really good - the Peacekeeper or Warrior, latter has a stiffer walking boot sole. Excellent and fit MY feet well
Magnums - only for street wear!
Nokian rubber boots - not tried (and you wanted leather) but I currently hunt in Skellerup Hikers
http://www.industrialfootwear.co.nz/footwear/gumboots/plain-toe/hiker - an ankle height rubber boot. Probably one of the most popular outdoor/hunting/tramping boots here beleive it or not!
Meindls - Borneo - blood good, if a bit rigid for flat UK countryside. Bloody dog chewed mine and the are 3 times the price here - paid 99 quid for mine 5 years ago.
But they must fit!!!!!!!!!!!