Heel slippage on monks/loafers? [shoe noob question]
In my experience, significant heel slippage has always been a deal-breaker. When your foot moves around so much in the shoe as you walk, it becomes incredibly uncomfortable, and causes significant creasing and wrinkling.
That being said, my understanding is that a slight bit of heel slippage is to be expected at first, and it will subside as the leather of the heel softens and conforms more to your foot.
Sometimes, however, it is necessary to go a little beyond this. Two remedies that have been suggested are: (a) heel grips (thin textured pads that attach to the inside of the heel) and (b) tongue pads that stick to the tongue, and which, at least in theory, help to push your foot back into the heel, thus reducing slippage. In my own case, I haven't had much luck with tongue pads (which have produced a little discomfort to the top of my feet), but the heel grips have helped a little. Wearing thicker socks with shoes that slip should help a little too.
I've heard that shoes can be "tightened" a little by a skilled cobbler, although I haven't had this done. Perhaps another forumer can comment on this. In the end, however, if none of these remedies solves the problem, you are right and truly screwed, and the shoes will likely just end up unworn.
The heel grips sound like a sure thing until the shoes break in more, I don't think the slippage is enough to warrant another hole or narrowing the shoe any (I hadn't heard of either of those things until your post!)
I think I may have finally found the answer to slipping heels. I went shopping for smoking slippers (studded) and couldn't believe how loose they all were in the heel. But come to think of it, I have had that problem with almost all shoes, including dress pumps. I bought a pair online hoping the brand name would make a difference; but not so. What I think has happened is that shoes manufacturers are getting lazy and forgetting about true fit. I recall that in the past I was able to buy shoes that were a B at the front and an A in the heel. This is called a combination last. As far as I can tell, this construction is hardly available any more, at least in designer type shoes. Trying to get these new shoes to fit, I bought some heel grips with little effect. I bought pads for the ball of the foot, and although they pushed the foot back, the heels were too just too wide. That was the key: the heel is just too wide. So I started installing the heel grips on the side of the heel (on the inside of course). This made the heel narrower for a much better fit. I can now wear my smoking loafers without the heels flopping all over the place as I walk, and I'm going to try this fix for dress shoes as well.
By the way, what are monks, anyhow?