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[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

The Maeve Hanky Hem Midi Dress from Anthropologie is a vibrant kelly green printed with French Riviera city names Saint-Tropez, Cannes, Biarritz, Cassis, with navy trim at the neckline, shoulders, and hem that ties the whole look together

How amazing are they

The challenge will be the hem

Close jar and shake well to combine