Ever do a Google search for "gifts for short men?" Don't do it, unless you want to get a little infuriated. Most gifts for shorter guys are made as gag gifts.
We know how challenging it can be to shop for a boyfriend, period. When he is below average height, however, that gets even more challenging. Feelings about height can get pretty complicated, especially with how height is strongly emphasized in today's male stereotype. A short guy might feel like the deck is stacked against him, and in many ways, he's right. 
At TallMenShoes.com, we want to help. We have some great gift ideas below, but all of them require him being on board. That means you should be close enough to your boyfriend to know exactly how he feels about his height, and how important that issue is to his work life, social life, etc.
Quality Elevator Shoes make an outstanding gift, as long as he knows about them beforehand. That sounds counterintuitive, because it removes the surprise aspect of a gift. Trust us on this: You'll still get a chance to provide a surprise. For now, he needs to learn about how Elevator Shoes do more than just provide extra height. There are posture and profile advantages, as well.
Once he learns about them, that's when you can surprise him with a high-quality pair from CALTO, TOTO or CALDEN. Keep the first pair in a casual style that can be worn in a variety of work and social situations.
If you go the accessories route, go with things that get worn on the chest or above. Pocket squares and masculine necklaces are a good fit, here. If those don't work, then keep choices for below the chest simple and dark - no flashy watches or huge belt buckles, in other words.
Great fitting clothes also make outstanding gifts. Not everything needs to be about vertical stripes, after all: Hollywood is filled with well-dressed men who are 5-foot-6 and shorter. Look for a good long-sleeved shirt, an outstanding fitted blazer or slimmer cut, higher-waisted trousers. If you're going be adventurous with color, do so on the top, not the bottom, but stick to darker colors overall.
About all those gag gifts: Avoid them. He might expect that from his work buddies, but not from you. You're the one in his corner, after all.