So when taking a walk this lovely, late-summer morning (it is GORGEOUS here in New York), I saw an older lady park her car and walk into her house. She was in her late-60's, early 70's, and wore an ankle-length dress printed with multicolored flowers. She was pretty fierce. I couldn't have pulled it off, but I've seen many a girl in Williamsburg rocking a high-waisted skirt and huge hat. Born out of the floral trend, the 'granny chic' look is about a blend of old and new, mixing modestly cut garments, classic silhouettes, and fashion-forward styling.
It's a relaxed fashion, all about looking soft, pretty... and somewhat complex. Nothing should match exactly, but keeping items in the same color family or in complimenting color palettes allows you to incorporate more prints. You can never have too many flowers, ruffles, and bows when you're rocking granny chic. 
When in doubt about this look, accessorize! It's easy to recreate with a floral print dress, oversized cardigan, and a strand of pearls. Seamed or patterned stockings are instant vintage, and cat's eye glasses and silk scarves around the head also add a dash of Mad Men-esque glamour. Just make sure not to take the look too comtemporary; stay away from cleavage or an expanse of uncovered leg. You know that Grandma would NOT approve.
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