[just to add to the comment about the style of the shoe being key, even within the sub-category of penny loafer] Not to make you feel old, indeed were all headed down the same path but my father, now in his 80s, has also never worn a pair of jeans and I appreciate the associations you have with them
Choose items that complement your dress without overshadowing it
Hook and eye closure and back zipper
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I loved his pride in his house, his pride in himself and his sense of morality (and how that sometimes lapsed), and the way that he struggled with his place in society