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Prune in late summer or early fall. Wear gloves. Snip off new shoots at the base of the plant. Cut oleander stems to about half height you'd like for the overall plant. Shape your oleander.
On the whole, oleanders are low-maintenance plants that don't need regular pruning. However, you should aim to do a major pruning of your oleander at least once a year during late summer or early fall. This pruning will help you shape your plant and stimulate healthy growth.  Pruning at this time won't interfere with the blooming of the plant, because it is after the plant has already bloomed for the season. Don't prune past October. Pruning too late can make the recently cut sections of the plant vulnerable during winter. It's essential to wear gloves when you are pruning oleander. Oleander is poisonous, and while for the most part it's only dangerous when ingested, it can cause skin irritation and inflammation when handled. That is why it's best to wear gloves when pruning or handling the plant.  You may also consider wearing goggles if you have sensitive skin or eyes. Be aware that the toxin in oleander is primarily in the sap of the plant. New shoots, also called suckers or basal shoots, are offshoots of the plant that grow up out of the base of the plant. Use sharp gardening shears to snip them as close to the base as you can. You can also dig up the dirt around the shoot and tear them out of the ground to remove them. These shoots can be harmful to the overall health of the plant because the plant will start to dedicate its energy into maintaining the shoot, rather than investing all its energy in the oleander. If your oleander is too tall and its size is a problem, you will want to cut it down to size. Since pruning oleander actually encourages growth and branching, cut stems at half the desired height of the plant. For instance, if you'd like your oleander to be four feet tall, cut stems at two feet. Your oleander will continue to grow, and will reach four feet when the branches grow in. If your plant is more or less the size you'd like, you do not have to do any drastic cuts. After cutting the stems to the desired heights, decide if you want to change the overall shape of the plant. When cutting branches, make your cut with sharp gardening shears just above the leaf nodes. The nodes are the sections where three leaves come out from the branch. Cutting just above the nodes encourages flowering.  Your plant may have some scraggly or overhanging branches that distract from the natural shape of the plant. Cut these branches to emphasize the natural shape of the plant. You can also reshape the oleander into more of a tree-shape by cutting off branches near the bottom of the plant, leaving the area around the base clear.