From which side should the man escort a woman? — Eartha in Dallas, TXAunt Dandelion answers:
Ah, the good old days, when men escorted women … and women insisted upon this mark of deference. In today’s society of independent, self-reliant women, some men might be afraid to even try to escort a lady. However, fear not, Aunt Dandelion is here to assure readers that the concept of escorting is still very proper and desirable in every social situation.
Indoors, the gentleman offers his left arm to the lady, as they walk together into dinner, the theater, or a social event. She grasps his upper arm, as opposed to just linking arms.
Outdoors, the gentleman walks on the side that places him nearest the street, to protect the lady from traffic, mud splashing, etc. If an obstruction looms and the two cannot pass it side by side, the gentleman hands the lady forward and follows her single file. If the obstruction is either dangerous or physically challenging, the gent goes ahead and offers his strong hand to his companion to assist her.
As always, the rules here are based on common sense and situational awareness.