J. C. Thompson wrote that pleating to the stripe is considered a more military look (he actually describes it as military pleating - So You're Going to Wear the Kilt, p. 57, third edition), while pleating to the sett is "civilian".

To me, it would really depend on the tartan. I'd have to see the tartan each way to really decide. Plus, it can make a difference as to which stripe you pleat to, if there's a choice of more than one color. (For example, Scott Green has yellow, red or white stripes to choose from. Scott Red has just white or black).

Is there software that can do this for us? If not - someone develop it, please!!!