How should you stay dry?

Illustration by Mark Alan Stamaty

I didn’t like Edward Bellamy’s Looking Backward when I read it 16 years ago, but I think of it every time it rains. The 1888 novel depicts a Utopian Boston in the year 2000 where rain is inconsequential: At first raindrop, canopies roll out of buildings, turning sidewalks into hallways, rendering umbrellas extinct.

Unfortunately, we don’t live in a Utopia; we live with umbrellas. The word umbrella comes from the Latin word “umbra,” which means “shade” or “shadow.” Used as sun shades in ancient times, they became popular as rain protection in the 1700s and have since pushed their way into high culture, low culture, and espionage. While Mary Poppins and Christo used them to magical effect—Poppins to fly and Christo to decorate valleys in Japan and California—they’ve also been used for more sinister purposes. The 1981 James Bond film For Your Eyes Only depicts an umbrella with clawlike spikes that protrude from the tips of the canopy. Altered umbrellas are not only the stuff of fiction. In 1978, an umbrella was used to shoot a poisonous pellet into the leg of Bulgarian dissident Georgi Markov. The world’s most-analyzed umbrella may be the one connected to the assassination of John F. Kennedy. As Kennedy was shot, a man standing nearby, later known as Umbrella Man, opened his umbrella and pumped it up and down, though nary a raindrop was in sight. It’s no wonder the Republican National Convention prohibited umbrellas last fall.

Of course, most users seek rain protection, not a weapon. For that, they have a panoply of choices, from cell-phone-sized umbrellas, which succumb more easily to rain and wind, to golf umbrellas, which provide good coverage, but are cumbersome and a nuisance to fellow pedestrians. Since there’s no perfect umbrella, one must ask, is a fancy, expensive umbrella an “investment for a rainy day”? Or, like a pirated DVD, will a $3 Chinatown umbrella do the trick? I decided to find out.


1) Portability(10 possible points): Does a “pocket-sized” umbrella really fit in your pocket? What about your purse? Does it have a comfortable wrist strap? Is the handle easy to grasp? Is the umbrella so big you hit walls, stairs, or other pedestrians? Can you hold grocery bags, a purse, find your keys, open the door, and hold the umbrella?

2) Functionality(10 possible points): Does the umbrella open simply and quickly? Are the open/close functions logical or confusing? Does it close effortlessly, or does closure require a maneuver akin to the Heimlich?

3) Strength(10 possible points): For the ultimate wind test, I took my umbrellas for a spin on the Staten Island Ferry. There, I tested how quickly (and if) they turned inside out and how promptly they regained their composure. I also tested to see if they would break like the myriad umbrellas left in New York City gutters after a storm.

4) General Mobility (10 possible points): How well does the umbrella play with others? Can you jockey your way through a crowd? Does it open like it’s attacking someone? Can you get in and out of buildings, and in and out of your car?

5) Aesthetics(10 possible points): Most of the umbrellas I tested were basic black. Nonetheless, aesthetic differences abound. Some have cheap handles, others bunch up when folded; some are admired by passers-by, others elicit snickers.

6) Effectiveness(10 possible points): Most importantly: Does the umbrella keep you dry? Or is it too small to provide any protection? If it has vents that let the wind escape, do those allow water in?

The Results (from worst to best):

Brookstone Pocket Size Travel Umbrella. Click on image to expand
Brookstone Pocket Size Travel Umbrella

Brookstone Pocket Size Travel Umbrella, $20

This umbrella is for masochists. When attempting to wear the strap on my wrist, its rough edges scraped skin off of my hand. As for strength—it broke within 10 seconds of the Staten Island Ferry test, rendering it impossible to close. In addition, this umbrella’s open/close function is confusing—I often hit the close button intending to open it. The umbrella features a vented canopy designed to let wind escape so the umbrella doesn’t turn inside out. Note to all manufacturers: Wind vents do not work—they drip rain onto the user’s head. This umbrella received one lone high score for general mobility—the small size means it’s unlikely to poke someone’s eye out.

Portability:4 (out of 10)
Functionality:2 (out of 10)
Strength: 1 (out of 10)
General mobility: 8 (out of 10)
Aesthetics: 4 (out of 10)
Effectiveness: 2 (out of 10)
Total: 21 (out of 60)

Sharper Image Flat Briefcase Umbrella. Click on image to expand
Sharper Image Flat Briefcase Umbrella

Sharper Image Flat Briefcase Umbrella, $19.95

This umbrella folds flat to fit in a briefcase, but two of the “ribs” (spokes) broke during the wind test, causing the canopy to open in a rectangular shape. Unless you’re Flat Stanley, this is a major problem. Other significant hitches: I had to jam the umbrella into my stomach to shut it. It is, however, easy to open, and the strap won’t give you lacerations like the Brookstone. As for aesthetics, the flat, silver handle looks smart.

Functionality: 1
Strength: 0
General mobility: 8
Aesthetics: 5
Effectiveness: 1
Total: 22

Leighton Genie—The World's Shortest Umbrella. Click on image to expand
Leighton Genie—The World’s Shortest Umbrella

Leighton Genie—The World’s Shortest Umbrella, $20

The world’s shortest umbrella also gets my vote for “most useless.” First, the silver handle is too small to grip well. Second, the canopy arcs down so that you can’t see where you are walking; raising the umbrella for better perspective defeats the purpose of using one. Three things going for it: small size; a convenient and user-friendly wrist strap (which the wee Totes Pocket ‘Brella lacks); and acceptable strength.

Portability: 10
Functionality: 3
Strength: 5
General mobility: 0
Aesthetics: 4
Effectiveness:  2
Total: 24

Umbrella purchased from street vendor in Chinatown. Made by Lanza U.S.A.
Umbrella purchased from street vendor in Chinatown. Made by Lanza U.S.A.

Umbrella purchased from street vendor in Chinatown. Made by Lanza U.S.A., $3

If I had $20 for an umbrella, I would avoid those above, buy six Chinatown umbrellas, and purchase two iTunes with the change. Although the signature plastic hooked handle might elicit a raised eyebrow from brella snobs, it also makes it easy to carry. And what value—for three greenbacks, you get an auto-open button, decent coverage, portability, and more-than-minimum sturdiness. For that price, you can’t complain about some hazardous accidental opening and occasional resistance to closing.

Portability: 9
Functionality: 2
Strength: 3
General mobility: 7
Aesthetics: 3
Effectiveness: 5
Total: 29

Totes Pocket 'brella
Totes Pocket ‘brella

Totes Pocket ‘brella, $22

I was surprised by this umbrella’s performance, because I once owned a Totes Pocket ‘brella, and it gave me rain rage. I’m still not a fan—my hair got caught in the shaft on more than one occasion, and it blew inside-out as easily as Marilyn Monroe’s skirt. But at 6 inches and 6 ounces, it’s portable, and it did not break. The open/close function is straightforward, and it’s better-looking than its pint-sized competitor, the Leighton Genie.

Portability: 8
Functionality: 5
Strength: 2
General mobility: 8
Aesthetics: 5
Effectiveness: 2

Total: 30

Titleist Golf Seat umbrella
Titleist Golf Seat umbrella

Titleist Golf Seat umbrella, $110

My Staten Island Ferry companion dubbed this golf umbrella “the silver dynamo” because it was one of two that stood up to the wind test. If you’re looking for sturdiness, this umbrella’s for you. If you’re concerned with fashion, look elsewhere: This big mama is silver and has Titleist scrawled all over it. The umbrella does boast one unique feature—it doubles as a seat. Said seat, however, works only on grass and is propped up by a spear-like tip that, in a dense city, functions more like a weapon. While walking, I whacked my foot with it, and I speared my friend’s foot while stowing it under a table. Given that the seat feature likely pushed this umbrella into the $100 range, I’d just as soon do without.

Portability: 4
Functionality: 8
Strength: 10
General mobility: 4
Aesthetics: 0
Effectiveness: 5
Total: 31

Lulu Guinness Shoes Folding Umbrella
Lulu Guinness Shoes Folding Umbrella

Lulu Guinness Shoes Folding Umbrella, $32

This umbrella, which features whimsical drawings of shoes, boots, and sandals in every color, may seem too pretty to do the job, but it’s surprisingly more resilient than most foldables. In fact, it requires strength to tame its quirks. Once it turns inside out, it’s difficult to revert. The automatic-open button frequently requires a supplemental push to completely unfurl it. Brute strength is necessary for closure, since it’s über-eager to spring back into action. This umbrella gets kudos for being purse-friendly, but the fabric is difficult to fold in the collapsed form; once you use it, it will never look as comely again.

Portability: 8
Functionality: 4
Strength: 4
General mobility: 6
Aesthetics: 5
Effectiveness: 5
Total: 32

Windpro from ShedRain
Windpro from ShedRain

Windpro from ShedRain, $38

This brolly sports a 68” arc, making it the Hummer of umbrellas. The generous canopy also caused quite the Mary-Poppins moment on the ferry. The umbrella was forced open by the fierce wind and nearly blew overboard. Ferry riders gathered to watch me wrest control: “You’re going to break your umbrella!” someone cried. When I finally closed it, the now-mini crowd erupted in cheers. If it weren’t for its Brobdingnagian size and its stick handle, the umbrella—which received high marks for functionality, strength, and effectiveness—would have scored higher overall. Perhaps a smaller ShedRain would have fared better.

Portability: 2
Functionality: 8
Strength: 8.5
General mobility: 2
Aesthetics: 2
Effectiveness: 10
Total: 32.5

Sharper Image Large Windefyer Umbrella
Sharper Image Large Windefyer Umbrella

Sharper Image Large Windefyer Umbrella, $34.95

Ironically, this “windefying” umbrella, described as “gust-proof in 60 mph winds,” did everything well, except stand up to wind. It turned inside-out easily and was a great challenge to revert to its intended shape, given its “vented” canopy (the “vented” canopy is essentially the frame of a small umbrella, supplemented by a circular flap around the inner frame’s circumference). In every other respect, the umbrella tested well. It boasts a large coverage area and a straightforward open-and-close button. The wrist strap and the shoulder bag function nicely, and the sturdy handle and sleek button make it relatively stylish for a basic black umbrella. For a walking urbanite, this is my pick for a nonwindy day. (Hammacher Schlemmer makes a nearly identical, though slightly less aesthetically pleasing, umbrella: the Wind-Defying 58” Compact Auto-Open Umbrella for $29.95.)

Portability: 8
Functionality: 7
Strength: 3
General mobility: 6
Aesthetics: 8
Effectiveness: 5
Total: 37

Lippincott Umbrella from Brella Bar
Lippincott Umbrella from Brella Bar

Lippincott Umbrella from Brella Bar, $225

I would call this the Bentley of umbrellas, except Brella Bar, the Manhattan boutique that sells it, has another umbrella they call the Bentley of umbrellas. That style goes for $325. Still, the Lippincott looks and feels as nice as its price tag suggests. The shaft is made of one piece of solid hickory wood, and the canopy opens and closes as smoothly as the door of a Benz. The heavy canvas cloth and solid construction mean it can withstand the gustiest winds. This umbrella is large, but the hooked handle makes it easy to carry—it dangles nicely from the wrist when opening doors, holding bags, or answering the phone. The only problem—aside from the price—is that the weight of the wood and the thick canvas tired my hand. If you have $200 and change to blow on something you may very well lose, this umbrella is for you.

Portability: 6
Functionality: 9
Strength: 9
General mobility: 6
Aesthetics: 10
Effectiveness: 6
Total: 46