I have been thinking of sewing my Integral designs gaiters on to my kayland Arya shoes. I already have some polyester non-wicking thread. I have tried using a regular needle and I have difficulty punching the leather. Should I use a sewing awl, any other techniques that work.

A leather needle might work, even if your sewing machine motor isn't strong enough to punch through you can work the machine by hand. But if the throat of the machine doesn't work well letting a shoe get under it than a sewing awl is the way to go. Awls make surprisingly sturdy stitches but will be much slower than a machine. I like to use light colored thread when stitching to a shoe so I can see the interior thread inside the dark interior. If the gaitor is a light material, this might be something to consider.

You could get a sailmaker's palm, made for sewing sails and ropework. If has a pocket with some hard material that helps to push the needle through tough stuff. If you really can't make it through, you could try drilling it, but with caution-- the bit will catch on different layers and twist the tool or the shoe right out of your hand, as well as making a messy hole.

http://www.westmarine.com/webapp/wcs/stores/servlet/product/10001/-1/10001/151051/10001/10900/11208/2

I suggest using a sewing awl, make life easy.