Dear Michael:

I carry a Taurus 85 snubby as BUG and primary when my P1445 won’t be discreet.

I’m looking at ankle carry as an alternative to pocket carry (left front).  I wear full height cowboy boots, hiking boots, or running shoes.

Are there any pointers you can think of about ankle rigs relative to these three disparate choices?

Dear JM:
I hope this note finds you well.
Thank you for the great question.

First, here are a few general ankle holster tips:
Consider buying your pants several sizes longer than you need. Then have the tailor or seamstress hem them up to the correct length. This will give you a wider cuff and aid in access and the draw.
Also 99% of tailors or seamstresses have cut clothing around handguns for other customers (check first.) If you have a dummy gun bring it in when you get the work dome and they will cut the pants for best fit, optimum access and concealment.
He or she can do this by angling the material on the gun side so that the bulge of the gun will leave the cuff “square-and-level.”
Years ago, some state trooper would also have the lower seam on the bottom of the pants slit and re-sewn with Velcro. Than way in an emergency the cuff would pop open wide and insure maximum access. Except for catching on a burr (?) the pants would never open and if they did the natural drape of the pants leg would still cover the weapon until you got to the men’s room to fix the seam.
If you occasionally switch the gun from the right to the left leg be sure to have her hem both legs so you can move the gun to the other ankle at will.
Boots are tough footwear to work with when trying to mate them with ankle holster. Some holster makers produce calf height holster that ride well above the boot. But the length the pant leg needs to be raised mush higher for accessing and generally this makes the rig less practical.

A possible option is to send the boot to the holster maker and have him stitch the ankle holster directly onto the boot. If the holster maker won’t or can’t work around the pre-existing boot, you may want to consider having the boot maker add a holster. Again, years ago I remember seeing boot makers offering to the police trade boots with built in holster.  

I hope a little of this information is of some value.
Thank you again for the great question.
I hope we will get on the range together sometime soon.