What to do when your boss gets you a holiday gift, and you're empty handed?

I don’t see the problem. Bring them each a thoughtful gift when you return. You can mention you planned it. Recieving a gift doesn’t ever require a return gift. That’s like the endless, “Thank you”, “You’re welcome”, “No, Thank YOU!”, comedy routine.

Your boss may not be able to except gifts.

Give your boss a hug.

Gifts, like s – - -, roll downhill.

If you’re leaving for vacation, you have the perfect excuse to bring back a yummy treat from whereever you visit, and leave it by the coffee machine as a present for the whole office (make sure to send an email around to your whole team so people know it’s from you!). ie, get local chocolates from wherever you visit, or if you go somewhere exotic, bring back a special treat from that city/state/country. It’s a nice gesture for everyone, and doesn’t seem like you’re just trying to awkwardly compensate for being empty handed earlier. Another alternative, if you’re a good cook, is to bake something at home and bring in cookies for your whole team/department/office (depending on the size of your workplace). If you’re feeling ambitious you could individually wrap them in colored celophane paper and put little “happy new years” notes on them for your coworkers and bosses.

For what it’s worth, my direct supervisor and my boss’ boss have bought everyone on our team holiday presents every year, and none of us has ever bought them something in return—it’s too awkward to buy a present for the boss without looking like you’re kissing up to them. I think it’s common for managers to buy their supervisees gifts, without expectation of something in return. If you do a good job, you make your manager look good every day. And trust me, as someone who has managed staff before, that is a real gift to them.

Putting some thought into it to indicates your appreciated.
You’re putting some thought into it as well asking us.
However don’t rush, appreciate the gift when your leaving tell them how much you liked the gift and how thoughtful they were.

While your away send them each a post card really nice one and thank them again. Being remembered is really a gift to most people. Then when you get back give them your special tokens from your trip.

Most people don’t give gifts thinking what am I going to get, and those who do don’t deserve that much thought anyway. these two will both feel appreciated if you just remain thoughtful and don’t rush it. That may just come across as cheap.

Just be really happy and thankful and get him something later if you like. Your boss wants to make you happy and when you give him this it makes them feel good. Gift giving isn’t a game of tag.