Wait until early fall in September or October to prune oleander. Later pruning than this will halt new growth in the spring.
Cut the bottom and side branches back to the width you want the plant to be. Make cuts just above a leaf node so the plant can branch back out after pruning.
Cut the top branches back to the height you want the oleander. Make all cuts just above a leaf node.
Remove the cut branches and compost them or discard them. Do not leave them under the oleander or they can harbor pests and infection.