Trim deciduous holly bushes such as winterberry (Ilex verticillata) in the winter months, before warm weather sets in and new growth begins. Wait until the last frost date to trim evergreen holly shrubs so that a cold snap will not damage emerging new growth.
Remove weather-damaged and broken branches from holly bushes, using long-handled pruners. Reach in to cut the entire branch away at the point where it meets a larger, main branch or the shrub's trunk.
Cut the lowest branches that no longer bear leaves, away from mature inkberry (Ilex glabra) bushes to prevent a leggy appearance. Trim back as much as one-third of the upper branches of older plants to rejuvenate the bush and encourage new growth.
Snip the tips off evergreen holly bushes, such as Blue or Meserve holly (Ilex x meserveae), that you have pruned into rounded, pyramid or other topiary-type shapes. Use hand-held pruners to allow for precise control of the cut.
Examine evergreen Japanese holly (Ilex crenata) and other types of holly bushes used for foundation plantings to ensure they don't brush against your home's exterior walls. Trim the bushes back to at least 6 to 8 inches away from the structure.
Check the growth of holly bush hedges, especially along sidewalks and adjoining land. Trim back any branches that encroach on public right-of-ways or neighboring property. Promptly remove all debris that results from trimming.