Assuming you want to accomplish this with a small amount of delta-v one of the better ways to do it is by using Jool/Jupiter.
This gives you two advantages:
1) The gravity assist from Jupiter will lower the delta-v needed to increase your orbit out to Pluto
2) You can use the large planet for a really cheap inclination change (as you approach Jupiter use a small normal/anti-normal, depending on the direction of the inclination change, burn so that you encounter Jupiter above/below its equator)
As a side note, although in theory it would be possible to intercept a large inclination planet without matching its inclination, its darn difficult... like trying to shoot a moving car, except the car is traveling 500mph.
