What to Wear takes the guesswork out of dressing for Boston weather

What to Wear Email

Boston weather is a fickle mistress. Whole seasons transpire over the course of a single week, and precipitation is despairingly unpredictable. Especially with spring trying to elbow its way into the weekly forecast, dressing appropriately for Hub weather can be a crapshoot – doubly so when you’re groggily rifling through your closet before work.

Enter What to Wear Daily Report.

The brainchild of HubSpot user experience director Joshua Porter, What to Wear is a daily email that aggregates weather predictions and makes suggestions about – you guessed it – what clothes you should wear. If it seems simple, that’s because it is.

What to Wear provides a quick, cleanly designed overview of the day’s weather that even the most woebegone 9-5er can digest in a glance in the unholy hours before punching the clock. The free messages are mailed out to subscribers by 6 a.m. and contain stylish diagrams detailing which shoes, tops, bottoms, and extras users should don to prepare for the day’s conditions. These diagrams are presented alongside helpful notes about road conditions, exercise suggestions, and even a philosophical Thought of the Day.

Now, Porter isn’t a meteorologist, nor does he claim to be Al Roker. He’s just a regular guy who was fed up with playing chicken with his armoire.

Well, a regular guy with a decade-plus of interface design and a degree from Rensselaer Polytechnic.

And, of course, Boston’s capriciousness with the thermometer made the city a perfect incubator for the project. Says Porter, “The weather really is a core part of our lives here because it’s always changing.”

Citing business theorist Clayton Christensen’s jobs-to-be-done framework as an inspiration, Porter built What to Wear to simplify a very specific daily task. Weather services, he says, give users too much information. What to Wear processes this information and distills it down to the most relevant bullet points.

“The initial idea came from a simple observation that people check the weather in order to figure out what to wear,” Porter says, “Normal people only need to know what’s going to affect them during the day.”

Though it sounds sophisticated, What to Wear isn’t the most high-tech endeavor. Porter manually compiles weather data each morning using an algorithm he’s developed in his head. Then, he separates the information into two separate reports (one for men and one for women) and hits send. The whole process takes about 20 minutes, and the results are surprisingly accurate, though precision isn’t Porter’s chief concern.

“The idea isn’t to get complete accuracy,” he says. “The idea is to make people confident that they’re prepared for the day.” Even so, Porter has found that being a weatherman can be a contentious part-time pursuit.

“People have a pretty low tolerance for when I’m wrong,” he says. “If I don’t tell them to take an umbrella, and they need an umbrella, that erodes trust in the service extremely quickly.”

Though it is currently only available in Boston, interest in expanding the service has been expressed in, among other cities, New York and San Francisco, and Porter foresees nationwide beta testing in What to Wear’s near future. However, he’s cautious to rush anything to market.

“Our plan right now is to slowly verify that we can produce an accurate weather and clothing recommendations across the country,” he says. “The first-time use experience for people is increasingly important, especially on mobile.”

Though Porter claims that he prefers compiling the reports manually, that workflow isn’t scalable. In preparation for this growth, he’s begun testing automation methods. He also aims to make the service much more customizable, admitting that even he doesn’t always follow his own advice.

“I usually don’t wear hats or gloves,” he says with a laugh. “I run pretty hot.”

Future incarnations of What to Wear will take personal quirks like this into account and tailor advice based on temperament, personal style, and even workout regime. In order to make this a reality, Porter is relying heavily on user feedback.

“I do my job by basically listening to people, understanding why they do what they do,” Porter says. “I regularly interview people, I regularly ask for feedback, and all of that directly effects the features that I implement.”

As long as What to Wear is helping Bostonians make sense of their city’s erratic weather patterns, the forecast looks good for Porter.