It isn’t quite as big as the ones I have but it is there. From the digi listing, the mechanical drawing shows the lip:
it looks to be only .5mm, and the one dimension missing is the diameter of that lip but calipers on the part will give you that, but with a hole the lip fits into you save .5mm in height on the top and .85mm on the bottom (you may only get one or the other because the LCD hole won’t be changeable, so I’d go for the 0.85mm saving on your board.) I think the ones I have are similar about a 1mm lip on the top of the pin, not much but also easy to recover with a simple hole size change on your board.
How much of a problem would it actually be to leave the holes at 0.043"? Would 0.008" really be that significant? (I haven’t soldered anything in many, many moons.)
Solder isn’t all the strong, you usually want a fairly tight fitting hole to provide mechanical strength, and in this case you are going to have movement as well which will make things worse, so I expect it is desirable to have the holes as close to the pins as practical, bending the pins of the connector over so they lay against the pad and hold the connector in mechanically would help some. The usual recommendation is have a strong mechanical join before soldering. All that said, I don’t have any experience with wearables, so you may be best to ask in the adafruit forurms or a wearable forum somewhere what people who have done its experience and recommendation is.
