Well, you are so right.. Trying to wear heels that are ill fitting, or too high will only result in pain and frustration during extended outings. The strange thing is that a higher heel does not necessarily correlate to difficult/painful walking. Sometimes, a lower heel can be uncomfortable, I guess it all depends on how the shoe/boot is engineered. And block heels are not necessarily easier to walk in than stilettos. I am guilty of buying used boots that are a bit too small because I love the style or the way they look, thinking they will "stretch out" is usually a waste of time.
I did gamble on this new pair of Sam Edelman boots with 4.5" stiletto heels, these are women's size 10s, I usually wear 11s. I am so thrilled because they fit perfectly with thin no show gym socks, or perhaps some hose/tights. These boots are so easy to walk in, even when compared to the block heeled boots I own, except my Frye cowgirl boots with 3" heels. Sizing varies so much between manufacturers, even different styles from the same manufacturer. Be sure to check return policies before buying new boots online. I wear these Sam Edelmans so often, I recently found another new pair and bought them quickly. Needless to say, stiletto boots aren't the best choice for extended wear outside on the streets, have already replaced the heel tips three times.
I always wear my boots with levis, but like 511s best. The latest pair of 511s has a little stretch to them, so they fit perfectly over my boots. Sure hope someday I will have enough confidence to wear my boots over my levis. I don't have the bod to pull off much from the "other side of the store", but feel I look good wearing guys clothing with boots. Just wish my better half felt the same way....D