The Franco Sarto loafers (top right) are stiff and definitely require breaking in! They were gifted to me and not very comfortable- I’m still on the lookout for less stiff platform loafers. The Sam Edelman flat loafers are the other hand are some of my most comfy shoes! For those, I’m usually between 5 and 5.5 and went up to the 5.5 in this particular style. Some have also shared that they fit a little narrow if you have wide feet. I have the no show socks I wear with these linked on my Amazon page (Amazon.com/shop/ExtraPetite) LTKstyletip LTKshoecrush LTKSeasonal