The stiletto has been called impractical.

As footwear goes, they’re not the easiest to walk in — not without looking like a supernatural life force is fighting for control of your lower body.

Those long, slender heels work against the natural function of the foot, which means they can be torture for a set of delicate human hoofs. They’ve also been known to commit atrocities against a defenseless hardwood floor.

But stilettos aren’t functionless.

They’re useful for aerating the lawn or tenderizing meat in a pinch. They’ll make do in lieu of a hole punch at the office, and can be used to stake down a tent while camping.

And while the traditional sneaker seems like the go-to shoe for comfort, what’s a sneaker going to do when you accidentally drive your car into a river and need a readily accessible way to break a window and swim to freedom?

Of course, the sneaker — with its flexible sole and accommodating arch support — does trump the stiletto in one vital area: The 100-yard dash.

Three-inch (or taller!) stiletto heels make runners unstable and prone to tumbling, which explains why stiletto races are so fun to watch.

The second annual Ski Boot and Stiletto Challenge, which happens at 6 tonight in the DiMillo’s on the Water parking lot in Portland, offers just such a stiletto-spectating opportunity. The event pits stiletto-wearing racers against each other in a 100-yard sprint to the finish line.

This year’s races also include a ski boot heat for runners who prefer the Frankenstein-like clod that ski boots are so well known for. Teams of four can enter the team relay category, which allows teams to don their preference of boots and/or stilettos.

And while the races make for an entertaining evening of awkward dashes and potential crashes, the Ski Boot and Stiletto Challenge is also raising money for noble local causes. Proceeds from the event benefit the Lift Up Foundation, Stepping Stones and Fight PLGA.

The fundraising aspect is what inspired Scott Manthorne to organize the event in the first place.

“It originally came out of wanting to support the three nonprofits,” said Manthorne. “I saw the stiletto thing and thought, ‘That’s something silly enough that people will pay attention.’ “

Registration costs $30 for an individual and $75 for a four-person team, and all races are open to men and women. Registration can be done online at or at DiMillo’s from 5 to 6 p.m. today. The first race of the evening — the ski boot race — takes to the starting line at 6 p.m. The team relay comes next, followed by the evening’s highlight, the stiletto category.

An array of prizes are up for grabs, including massage gift certificates, personal training, restaurant gift cards and certificates to nail and hair salons, among others. And every race entrant will receive a free early-season lift ticket to Saddleback Mountain in Rangeley.

Following the races, participants and spectators are invited to an after-party at DiMillo’s on the Water for food, raffles and live music from Last Kid Picked. Prizes will also be given out for best stiletto and best outfits (i.e., costumes aren’t required, but are absolutely welcome).

And who knows, someone might lug out a block of ice from the freezer, conveniently slip off a high heel and become an impromptu ice sculptor. Stilettos are good for that too.

Staff Writer Shannon Bryan can be contacted at 791-6333 or at: [email protected]

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