A bossy figure is always difficult to handle. But if you are literally thinking about giving a special gift to your boss who is bossy as well as picky regarding the gifts he receives, then it must be a challenge for you to pick the right thing for him.
You may look online for various options and ideas so that you know which of the possible gifts are suitable for your boss. Though it should not be too difficult for those who know their boss, which things he loves and how he wants things to be presented to him. But still, care must be taken so that the impact of the gift will be in a positive manner and not vice versa.
For sure, you have to keep respect in mind especially when your boss is an older person. You may also consider his interest in mind when selecting things. The age, personality, interests and personal preferences must be considered when buying a perfect gift for your boss.