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How to Sell Sweatpants … And Everything Else

Updated: Nov 19, 2021

I loved fashion once. When I worked at The Telegram I used to keep high heels in three different colours under my desk, right next to my snow boots with an extra pair of socks inside. I visited Model Citizens weekly to buy designer brands off a sale rack (I loved fashion, but I was poor lol). I had piles of fashion magazines.

Changing My Pants

At some point along the way, I stopped dressing up for work. Whether I’d worn this dress last week or the week before was too much to think about on top of my growing responsibilities. When we started Rogue Penguin, I did a lot of video meetings which allowed me to wear more comfortable clothes. I was working way more hours as a new business owner and most of those were from home. Sweatpants happened.

Three years into owning this business, a global pandemic hit and suddenly everything was virtual. There were no more coffee shop meetings, no more board rooms, and sweatpants became the one good thing about it.

Betting on Fashions' Failure?

Scott Sternberg, a fashion designer, had a similar trajectory. Most of his story is outlined in this New York Times article. The story talks about how Scott started his company which focused on cozy basics and how he watched the fall of big fashion through the early months of the pandemic. Specifically, the bankruptcy of fashion mega earners like J. Crew, Neiman Marcus, Brooks Brothers and J.C. Penney.

The most interesting and best part of the article for me, however, was a very specific email Scott sent out to Entireworld’s 30,000 subscribers without ever running it past employees. It read;

“Wow. I mean, WTF. Am I sick already? Can I leave my house? What do I tell my employees? Will my mom be OK on her flight home today? Can Zod” — Sternberg’s dog — “get coronavirus? Did I buy enough T.P.? How long will this last? Who’s in charge? What’s next?”

In These Difficult Times

The email - sent among a tidal wave of “we care about you” emails from big brands, was so ... human and relatable. What’s shocking is what happened next. The company which used to sell 40-odd sweatpants per day, began selling more than 1,000 per day. When the sweats ran out, people bought other items from the shop, driving sales up 662 per cent over the same month the previous year.

Obviously Entireworld wasn’t the only beneficiary of this crash in fashion, as the sales of sweatpants were up more than 80 per cent across the board in the United States alone. However, what Scott did with this one email was a key factor to his brand getting noticed above and beyond others’.

That email, so simple, so vulnerable, was what customers needed. As we all see ads with “in these difficult times,” repeated over and over, it was the personal and the direct reference to what was making these times so damn difficult that really connected with people.

Lesson Learned

We’re all learning a lot of lessons from the pandemic, but this is one I’ve known and pushed on our clients all along. Interacting as a human being with empathy, humility, and respect - even on cold computer-based platforms - will always be a better selling tool than deals, empty promises, and fantastical claims about your product.

Share the humanity, share your stories, and consistently relate to your clients for the best outcomes. You might even feel better about your business too!

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