I'm currently walking around with this very Magritte-esque collapsible Tibor Kalman-designed model, which you can get for $35 at MOMA. I can certainly attest to its sturdiness; I've had it since last June and it's still in great shape. And it helps me to smile every time I look up, no matter how dark and cloudy the sky may be.
I love the print and curved wooden handle (which is rarely seen in collapsible umbrellas, on this model which is $38 from JCrew.
The abstracted floral print on this $30 Marimekko Ruusupuu umbrella from Luna Boston is undeniably adorable.
The vibrant shades and cartographical flavor of this Juicy Couture umbrella from Neiman Marcus are hard to diss, though it's pretty expensive at $75.
For those of us who keep our tongue firmly in cheek, this umbrella emblazoned with a fabulous quote from Marcel Duchamp is perfect! At nearly $80, however, the price is less perfect. This parapluie from the V&A's gift shop reads, “Esquivons les ecchymoses des esquimaux aux mots exquis” or "dodge the eskimos' bruises with exquisite words." Indeed.
Most of the umbrellas here are brightly colored; this pinstriped model, also from the V&A shop is more sober but still makes quite a statement. Interestingly enough, it was designed by Jean Paul Gaultier - best known for his often extravagant fashions.
For the more discerning in taste, here is my personal favorite - a rare and gorgeous Fornasetti "Montgolfiere" umbrella, named after the creator of the first hot air balloon. The Montgolfiere also comes in red, blue, white and black. While it is perhaps the most beautiful of the umbrellas I picked, it's also the most expensive at $127.27.
A very minimal statement is made by the Bubble umbrella, which is $18 at Urban Outfitters. Clear umbrellas like this were seen, among other places, in the hands of the Olsen twins and in Lost in Translation, and I think they're quite stylish.
For a interesting review of umbrellas that is rather more scientific than mine, check out this Slate article by Laura Shin.