You enthused about vintage umbrellas, but if you’re open to new ones as well, have I got an umbrella for you: I _love_ my Blunt umbrella, the only design tested never to invert even under direct gale-force winds (off a great little debut sitelet called The Grommet where I’ve found a bunch of other innovative gems over the past decade and counting), plus has stylish and safe rounded tips instead of daggers liable to poke somebody in the eye. I bought their nifty mesh carry sling a few years ago but sadly that seems to have been too forward-thinking for consumers because it’s not longer made (maybe they can be persuaded to bring it back…?). Please look them up, I suspect you’ll find them as delightful as I do.
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