I have been doing active development in C# for several years now.  I primarily build enterprise application and in house frameworks on the .NET stack.
I've never had the need to use any other mainstream high level languages besides C# for my tasks, since .NET is the standard platform we use.
There are some legacy Python applications that I have been asked to support going forward, I have no exposure to python and dynamic languages in general(although I've done a fair bit of JavaScript).
I was hoping to get some guidance/advise to aid in how to go about learning a language like python for the statically typed mind.
EDIT: Using IronPython is not an option!
There is a big initial hurdle of getting comfortable with dynamic typing. The first step is when you look at Python-code and realize that variables aren't defined anywhere, you just create them out of thin air, which feels like jumping over a cliff. There is a brief moment before your hang glider catches the air properly. 
And then it's going to take time before you trust your newfound dynamic wings, and you probably only can get their by doing aerobatics with them. Learn how python handles references, have fun with monkey-patching methods, duck type various animals. Try to learn some ugly tricks.
And although you can't use IronPython for this, there is no reason you can't use it to learn Python.
Learning Python for a .NET developer