Typically there are two schools of thought when it comes to umbrellas1.
1. Buy the cheapest ones possible. When it inevitably breaks, just buy another one.
2. Search for the most wind-resistant umbrella possible, cost be damned.
One of our investors at work is a believer of the first school. A bit over a year ago he showed up to work with a big box of dirt cheap, plastic, black, throwaway umbrellas for communal use. These umbrellas would literally fall apart upon opening. A child could bend the stem with one hand. But when facing a commute home in inclement weather with your own umbrella at home, it was better than nothing.
Personally, I've been following the second school for the past 2 years or so. My previous umbrella is this Brookstone one which actually worked pretty well. It had a pretty large 54" inch canopy yet collapsed down to a manageable size. Until one particularly wind-blown day when one of the ribs snapped like a twig. Even crippled it still works although one panel flops around like a fish outta water.
Earlier in the week, these Senz umbrellas caught my eye. Besides looking like the F-117 stealth fighter, I was intrigued by the claim that it won't invert under adverse wind conditions because that's pretty much the main thing I hate about umbrellas. So I ordered their mini folding umbrella which arrived yesterday. Now the mini is supposed to survive only 40mph winds (not 70 like their regular sized version) but it's also not as peculiar-looking as its larger brethren. It's not particularly impressive looking compared to other umbrellas. The ribs look fragile so I'm definitely interested to see how it'll actually perform come crunch time. Comes with a lifetime warranty though so that's something going for it.
And then Devon got his hands on it...
1 Ok, there may also be people who eschew umbrellas altogether but I've only seen one person who does that (or used to) on a regular basis. ;-p