A, for my recent trip to Israel, I did my usual thing and packed more shoes than most people would. For me, this is key to ensuring comfort -- both physical and emotional. I walked anywhere from 8 miles a day to 14 miles a day (never less) and my feet survived extremely well. The temps were probably similar to what you may have in Glasgow. Weather was anywhere from 8 C to 19 C (it varied quite a lot). It only rained once, however -- which is different from what is typical in Britain.
I brought:
1 pair slightly dressy chelsea boots with small heel (these were for "dress up" and travel but also cooler evenings).
1 pair high-top wedge sneakers (for walking and in case it was warm -- but could also be worn with socks).
1 pair Mary Jane walking shoe (Ecco) with sneaker type insert -- for hikes and warmer walks (broken in, no need for socks).
1 pair sandal booties (in case of heat and for dressier occasions)
1 pair flat oxford style golfing shoes that could be worn in rain. (Made of some kind of magic vinyl).
I wore the sneakers most. The temperature was unusually low for the season and not forecasted. Had I known that it would be so cool, I probably would have brought my Blundstone chelsea boots. This is the type of boot that most people in Jerusalem were wearing at the time. Super for walking on cobblestones. But my high-tops served the same purpose and worked with socks and without.
I wore every single shoe in this package. Often I changed shoes more than once a day for different activities.
I would highly recommend a pair of casual but nice looking Chelsea boots and you can grab them on sale now. Shannon had a super pair of Clarks and JackieC also bought them. They did sell them at the Bay but may be out now -- not sure. I'm not sure if the ones I pictured are the right ones, but you get the idea. The elastics make them comfortable and easy on/ easy off. They did come in black at one time.