It is great that we generally wear more concealing clothes and can move away from a summer (small) gun to a bigger or fullsize, but I see but see little on how to carry when you have to actually spend time outside.
Traditional holster logic doesn't really work. OWB, IWB works fine for when you are just going out to your car or smoking in the parking lot, but it is not the same when you are out for hours (or longer).
You still have to access the pistol if you need it. Not so easy under your multiple layers of clothing and winter jacket. Yeah, I can conceal my 1006 or a fullsize 1911 under my winter coat, but can I get to it without unzipping 3 jackets or spend 5 minutes of fishing through clothing layers to get to it?
Here is what has and hasn't worked for me:
IWB - clearly inside the waist isn't really going to work very well.
OWB (outside belt holster) - this might work if you can put the pistol only under your winter coat. I have considered getting a "duty belt" or a Wilderness to supplement my regular belt. You could wear it over all of your layers.
It would be great if you had a patrol jacket, like 5.11's, where there are actually snaps for quick access to a sidearm. I don't own any of these...yet.
shoulder holster - actually resizing this to go over all of the layers of clothes and under your main coat works pretty good. You still have to unzip it for access it, but is fairly comfortable. You don't have to worry about printing since you already look like a marshmellow.
ankle holster - depends on the type of pants and weather. Trekking around outside (at least around here) even if there is no snow usually results in wet pants and wet backup pistol. Not so easy to access when dressed like the Micheli-man...
man bag - I will be darned but I have found that increasing the strap size of my Maxpedition to fit over everything including the winter coat works REALLY well. Still gives very quick access to the pistol and quick carry of other things like a flashlight (since it gets dark befor 5pm now).
jacket pockets - my ski jacket had pretty good front pockets that were perfect for a mini-Glock or J-frame. My current favorite jacket is a Columbia 3-in-1 that has cavernous zippered hand pockets. I suspect mini-Glocks will work and possibly bigger.
If you have any ideas, I have missed let me know. Keep in mind that for me it has to be concealed so drop or offset holsters won't work.