A friend sent me this photo with the wish, "...I hope my friends are this young at heart and hip forever."
(Though many Facebook comments refer to her as "old", I read her as an early-middle-aged women who went white early.)
I enjoyed her well-wishes and at the same time, thought, No way I'd pick that shirt. (Among other constraints, the eyes would pop out at a distressing place on my chest)—but she projects joie de vivre and a whimsical style I'd call more "creative" than hip. Good for her for letting her feline flag fly!
Even if I wouldn't rock a giant cat face, I'm not averse to orange frames; below, me at the softball game/BBQ the evening before the kids' wedding:
Before you think I'm a badass instead: the event was licensed for the beer I'm holding.
As Tower of Power famously asked, What is Hip?
Urban Dictionary says hip is, "Cooler than cool; the pinnacle of "it"; beyond all trends and conventional coolness". (The related word hipster addresses a young-adult demographic; see entry here.)
To me, the ephemeral ether of hip inhabits a less capricious neighbourhood than Ms. Kitty's, more Rick Owens than Trash & Vaudeville. Hip is hatched from a confidence that rejects conformist behaviour such as ironing your hair straight when it's not (guilty, up to my mid-twenties) or starving yourself to size whatever while you're miserable.
The hip women I know are uninterested in copycat InStyle outfits, but always have one audacious detail, a scarf or an unusual ring, or 'their' way of wearing a hat. They are not necessarily pretty, but have strongly expressive faces, like these women:
Left, poet Anne Carson; centre, visual artist Shirin Neshat; right, filmmaker Agnès Varda.
Trying to be hip is like trying to be witty: effort kills it. So does hanging onto youth; as TOP sang,
"...and if you're really hip, the passing years will show."