Choose Boss' Day gifts by planning in advance and getting to know what the boss likes and doesn't like. The more planning put into the gift, the more he feels appreciated, and the less the giver looks as though he doesn't care.
Because Boss' Day is on Oct. 16 of each year, start planning ahead by marking that date on the calendar. As the time gets closer, pay close attention to some of the casual conversations the boss has in the workplace. Be alert to what he enjoys. Some conversations to make a mental note of include those that center around sports, hobbies, favorite restaurants and even the type of music he likes. Additionally pay attention to what type of snacks the boss likes to eat during the day.
Check out the boss' social media pages to see if he posts personal activities that he takes part in. Sites such as Pinterest can provide information on the types of clothing, home decor items and other items he might enjoy. If these things don't provide the perfect idea, talk with someone that the boss is closest to. Ask if they can provide ideas on what the boss needs or what he would like to have.