FatMax Tape Measure. I always used cheap tape measures or whatever was within easy reach until I used a Stanley FatMax. Now, I will walk past any other tape measure and to the other end of the shop or even out to my truck to get to the FatMax. That is saying something since my shop is 200 ft. long. They are accurate, durable and have a long reach. Christmas is a great time to splurge and by the expensive tape measure. The first FatMax I bought was $25 and worth it. They are less expensive now.
Combination Square. This is one of the key layout tools in my shop. For a gift, splurge and get a good one. An accurate combination square will be used on every project. Look for a cast iron tool as compared to aluminum. Starrett is the most coveted.
Nippers. Nippers are great for lots of applications. They work like a pair of pliers to help remove nails. Whether it’s pulling an errant brad in new woodwork or nails out of an old piece of trim, nippers get a lot of use. Nippers are more for on-site installation type of work, but I use them in the shop too. Mine are Channellock brand.
Premium Paint Brush. Like clamps you can never have enough paint brushes, but you sure can have too many bad ones. Go crazy this holiday season and give a $15 paint brush. I recommend a 2-1/2″ angled sash brush. There is nothing like a brand-new premium paint brush.
Drill Doctor Drill Bit Sharpener. Every woodworker and do-it-yourselfer has a box with drill bits in it that are dull. They are still good, but dull. Even guys that love to sharpen their tools have dull drill bits. Fix this wrong in the world and save the drill bits. The Drill Doctor is fast and works great, plus a lot of woodworkers don’t have one.
Small/Quiet Air Compressor. Many woodworking tools use compressed air. And like routers, it is fine (in some states required) to have more than one air compressor. For a gift, try the Senco PC 1010 or Senco 1280. I own one and love it. It is tiny, but will run a brad nailer and many other nail guns. It is super portable and ultra quiet. Do not, I repeat do not, purchase a Porter Cable pancake model. It is cheap and works fine, but it is the loudest tool in the entire world. I know guys that own one and they have extra long hoses so they can get the compressor as far away as possible, usually outside.
Japanese Saw. Great for flush trim work and small pieces. 
They are super sharp and cut fast. American companies make similar saws, but for a gift make sure it is Japanese.
Stocking Stuffers
Glue. Any name brand wood glue is good. I normally use Titebond with the red lid for interior work.
Note Pad & Pencils. I am a bit of a pencil snob. The best pencil for woodworking is a Dixon Laddie. It is a fatter pencil that won’t easily break, and it can be sharpened to a fine point or can make a bold line when needed.
Tape. I never have enough tape in the shop. A stocking full of 1″ blue masking tape would be a welcomed sight.
Utility knife. Everyone can use a utility knife. Put cheap ones in the stocking or buy a good one and give it as a stand-alone gift. Folding versions can be carried at all times and fit easily in your pocket.