I’m not able to take much time off this summer. The same cannot be said about my wingtips.
Even in the hottest months of the year, there have inevitably been occasions where I have had to meet in person with a client, attend a business function or even appear on stage as part of an industry event. When this happens you can usually get away with a golf shirt instead of a long-sleeve dress shirt and sportsjacket, and khakis or chinos can be swapped for what we once called “slacks” but some kind of dress shoes were still expected.
Much like COVID-19 has forced guys to question the value of even wearing pants to work, work-appropriate footwear is now largely ill-defined. Even wearing loafers, which were often my go-to in July and August, feels ridiculously unnecessary, almost an affectation.
The alternatives, however, are just as unappealing.
I want to wear sneakers when I’m out for a walk in the evenings or on weekends.
Flip-flops, slides and sandals will get the job done, but they make me wish I were close to water (or a tiki bar).
Leaving slippers on all day is the act of a man who had not fully committed to waking up.
This what was drew me to the idea of espadrilles, a style of shoe I’d long avoided.

Though they have a long and colourful history that was best chronicled in Esquire, espadrilles always struck me as too . . . European to be worn in North America without attracting snickers. Too relaxed for business, too much of a costume for after hours, unless you’re Aristotle Onassis boarding a yacht or something.
Summer 2020 changes all this, just as it’s changed to much else.
Today, wearing espadrilles feels like a step up from a sandal or a flip flop because your foot is entirely covered. It’s as relaxed as a slipper and unlike a sneaker, has a more elegant shape.
Espadrilles are also a closer cousin to dress shoes in that — even with materials as simple as canvas, cotton and esparto rope — they express a level of style, sophistication and intentionality. They work as a work-from-home (WFH) choice, even if no one sees them, but transition seamlessly into going out for a drink on a patio or a picnic somewhere sunny.

After scouring online, I chose to buy my first espadrilles from DIEGOS, a Quebec-based firm which manufactures its products in Spain by hand using organic materials.
“Authentic espadrille-making is an art that has almost disappeared due to globalization,” the company explains in a blog post. “Diego’s family originates from one of the last villages in Spain where our espadrilles are crafted following the centennial tradition.”
If you really want to get nerdy on the subject, Diegos has even filmed a documentary alongside a detailed photo-essay on the manufacturing process.
I just wanted the shoes, and the Diegos online store was simple and easy to use. The price was certainly right at less than $30. Shipping was also pretty fast — I think I got them in less than a week.
I opted for navy blue instead of black because, in summer, the espadrilles don’t simply take the place of dress shoes but a suit I might normally be wearing. I also chose a pair in grey wide stripes that gave me the flexibility I’d want in mixing a solid dress shirt or suit with something that had a pattern. (They also have gorgeous leather ones, but were sold out in my preferred colours and sizes).
What’s great about espadrilles, I’ve discovered, is that they breathe well and don’t require the hassle of no-show socks you need with loafers. I wouldn’t walk in them for miles, but that’s the point: everything about them says “Stay. Sit. Take your time.”
I’m still not sure how my wardrobe choices will have to evolve as we continue living through this pandemic. But embracing espadrilles has felt like a step in the right direction.