Proper leather shoes

In the army they told us to piss in our boots and then wear them! Or, you could just fill them up with water and then wear them. Maybe more hygenic...

875's are a classic. Can't go wrong with them in red.

Whats the best way of softening up a pair of leather shoes?
I'm getting some pretty mean bite around the ankle which is making them pretty unbearable to wear.

Try a hairdryer and a hammer. I've dabbled in shoe-making in the past...
or you could piss in them...

2 quick questions.

Whats the best way of softening up a pair of leather shoes?
I'm getting some pretty mean bite around the ankle which is making them pretty unbearable to wear.

Also, I'm thinking about in investing in some redwings for the winter.
Either the 875 or 9111. Any insight into what is good?

You could try a little mink oil. It'll absorb deep into the leather and should soften them up.
If you go for RWs then invest in Obernauf's LP. Wear them for at least a couple of weeks, then clean them, use a hair dryer to soften them then apply the LP by hand.

check this

I wouldn't use any of the recommended techniques for softening boots, just wear them for short periods of time initially and gradually work up to full time usage - they'll last longer.

Whats the best way of softening up a pair of leather shoes?

I've generally found using shoe cream rather than shoe polish effective at this.