Not sure which boxwoods these are at our new home on the eastern shore, what's the best time and method for pruning?
Box woods/Buxus
Haighr, I'm pretty sure that your 'boxwoods' are actually an Ilex glabra variety.
http://www.missouribotanicalgarden.org/PlantFinder/PlantFinderDetails.aspx?kempercode=d553
Give that man a Holly Society of America membership! Well, almost.
I agree with Sequoiadendron4 that those plants are not Boxwoods (Buxus sp.), because Boxwood have opposite arrangement of simple broadleaf evergreen leaves. The first three of the four images shown clearly have alternate arrangement of leaves.
I don't believe that these are Ilex glabra (Inkberry Holly) though. I think they are Ilex crenata - Japanese Holly. Some more images would be helpful. You could prune off any "wild hair" stems back within the outline of the plant's exterior - and then take additional closeups of various details under accommodating lighting.
Inkberry Holly tends to have more vertical and rounded habit, larger individual leaves, and next to no horizontality or stiffness. Japanese Holly often is broader than tall and is a very common foundation plant in the Mid-Atlantic region which takes to shearing like a pig to slop.
The fourth picture looks like a China Girl Meserve Holly (Ilex x meserveae 'Mesog').
http://davesgarden.com/guides/pf/go/80034/
Oh well, thanks VV, I tried :)
It pays to look beyond what seems obvious at first, and be sure.
Otherwise, one can end up with Amur Honeysuckle when anticipating Mock-orange, Dogwood, or Viburnum...
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