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None of those starchy, scratchy dress pants

If it's clear that you're too young to be from the era your wardrobe hails from, it may cut down on some people (at least those who know the basics of fashion history) assuming you're just wearing really old clothes and dressing "grandmotherly" (a term that personally, I've never been comfortable using in a derogatory context - one only has to look at websites like Advanced Style to quickly see that plenty of grandmas and great-grandmothers alike have killer style that can knocks the socks of that of scores of women several decades their junior!)

And, with great layers, comes great possibilities

Textured Satin Dress and Jacket by Komarov at Nordstrom 4.Gown by Carmen Marc Valvo at Rent the Runway 5