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Fit varies across the lineup

None of those starchy, scratchy dress pants

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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!)

It is how to choose the right shade, style, and occasion to make the pairing deliberate rather than accidental

Need a Measuring Tape