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“Is it possible to find comfortable walking sandals that still look good? I’m going to Europe this month and I can’t wait to get my steps in on the cobblestones. But I don’t want to wear the same running shoes I wore all pandemic. Are there sandals designed with foot health and comfort in mind that I won’t be immediately embarrassed by? Can I find some that take orthotics?” — Wincing wherever I walk

When I was young and arrogant and believed myself to be immortal I wrote a scalding story for a city magazine about the scourge of the Birkenstock. I dismissed them as a clunky relic of the hippie era, bragging about how my foot, accustomed to strappy stilettos, would cramp when offered a moulded footbed. The universe got the last laugh: I now have the feet of a 75-year-old, decades prematurely, and I deserve them for that next-level hubris.

That was a long time ago, before Birks became wildly fashionable through various collaborations with designer fashion houses. Now I alternate between two pairs of Birkenstock Arizonas — matte navy and metallic silver — all summer long unless I’m going to a wedding. I’m not alone: during the pandemic, the siren call of comfortable footwear lured most of us. And handily, the current generation of young immortals are wiser than I was: they have made what used to be considered “ugly” sandals cool.

Walking on a Cloud is the place to go for comfortable shoes, so that is where I went to seek out more info for you, Wincing. In the past 10 years, both its stock and clientele have become younger and hipper, says co-owner Lori Vella. She’s a second-generation comfort footwear purveyor — her father started his own shoe business in Toronto 60 years ago and Walking on a Cloud was folded into that, so the footwear knowledge goes deep. “We went in early on the Ugg trend and that brought in a new generation of customers,” Vella says. “Then we started to bring in youthful, boutique brands” like Gabor, Wonders and Redback. But comfort is at the centre of what they do.

“Fit is everything,” she says. “What works for my foot may not work for you.” Shoes, especially walking shoes and sandals, are something you need to try on or be prepared to return if they’re not quite right. “Keep trying styles until you get a feel for what works.”

When you go into the store, a high-tech gadget will help you find the perfect fit the first time. “We’ve just installed Aetrex Albert 3D foot scanners in three of our stores,” Vella says; the rest of the chain will get them soon. The scanner does more than determine foot size — it measures length, width, girth, and instep and arch height, and then produces a 3D model of your foot. All this info means staff can recommend shoes that will not only fit properly, but be best suited to your individual foot concerns. (Some problems need to be diagnosed and addressed by your doctor or a podiatrist, Vella cautions.)

“If you need an insole, the scanner will tell you what will work. You may still need a custom insole (from a podiatrist),” she says, “but we can point you to sandals that will accommodate either off-the-shelf or custom insoles.”

Here are Vella’s key sandal recommendations: look for lightweight footbeds cushioned with memory foam or air cushioning or similar. Flexibility is also important and adjustability, because your feet swell in the heat and when you walk long distances. Most of all, look for proper support.

When it comes to fabrics, Vella likes soft leather that is breathable. But there are some great EVA options — the acronym stands for ethylene-vinyl acetate, a naturally stretchy polymer that is bouncy — which makes for sandals that feel like running shoes. Vella says the Dansko Kandi sandal made of 50 per cent bio-based EVA is very popular, with a comfortable footbed, arch support and lightweight, easy-to-clean uppers.

Birkenstock also has a great EVA version of the classic Arizona sandal. Vella points out that Mephisto has “similar styles with arch and metatarsal support, made of quality materials. Mephisto's are fancier with prints, metallics and bling!”

If you’re venturing into the woods, or want to look like you are, the sporty hiking sandal has been a big trend for the past few years — Teva inspired Chanel in this regard, not the other way around — and isn’t going anywhere soon. Vella likes outdoor sandals by Merrell and says they’re a good choice for people who need wide-width shoes.

Another brand she carries is Ecco, from Denmark, which she says offers “excellent sandals for dress or hiking, with soft leathers, great support, anatomical footbeds and adjustability. And they’re flexible and lightweight.” They’re also looking to break into hipster closets, based on my review of their recent imagery. I asked the design team at Ecco how that’s going. “I’m not sure we’d talk about ‘fashion forward,’ but we’d definitely talk about ‘style forward’ and our hope is to create modern footwear which is both fresh and contemporary as well as being as timeless and investable as possible,” says Liam Maher, Ecco’s global creative director.

He points to the two-strap Cozmo sandal, one of the hottest styles right now. The construction is achieved using vacuum technology designed to “integrate the leather strap-set directly into the soft foam midsole formed simultaneously around a fully contoured last.” Not sure I fully get that, but it sounds high-tech. First and foremost, the design team’s goal is “a very particular type of comfort,” Maher says. “At its heart, it harmonizes cushioning with support.”

And in my heart, I hope that by writing a more positive piece about comfortable shoes, the universe will give my own achy feet a break.

Supportive sandals that are on trend, too

Merrell sandals, $130, merrell.com SHOP HERE

This cool sporty sandal has Merrell’s trademark contoured insole, and a bouncy EVA midsole — many of its components are made of recycled materials. The buckles are adjustable, to help you get the perfect fit.

Gabor sandals, $189, walkingonacloud.ca SHOP HERE

This navy and white Gabor platform sandal from Walking On A Cloud offers a dressed-up take on comfort but still delivers lightweight flexibility and adjustable straps. Perfect with a sundress.

Ecco sandals, $110, ca.ecco.com SHOP HERE

Ecco’s Cozmo sandal has easily adjustable leather straps fused to the anatomically shaped footbed, which is covered in soft suede. It’s sleek Scandinavian style made comfy.

Birkenstock sandals, $220, littleburgundyshoes.com SHOP HERE

Oversized buckles and colour-coordinated details add a stylish update to the tried and true Birkenstock Arizona. It still has the all-important anatomically-shaped cork footbed, EVA sole and adjustable straps.

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