Style

I Traded In My Stilettos for Sneakers, Now What?

I’m fortunate enough to live in a city that is very walkable and public transit-friendly. I love being able to stroll from work to galleries and restaurants, but I can’t seem to find shoes that are both comfortable and chic and can take me from my tech job to meetings with friends and exploring new neighborhoods. Can you help? — Alison, Boston


I can’t tell you how many conversations I had with peers during the last fashion week complaining that we had all lost the ability to tromp around all day in high heels. After about an hour or so, our calves would start to seize up, the balls of our feet begin to ache, and we would revert to the sneaker-shod form of the past indoor year.

Which did not feel like a step forward (so to speak).

There are a variety of solutions: Queen Elizabeth II, for example, wears pretty much only square-toe pumps with two-inch heels that have been broken in by her senior dresser, Angela Kelly, and she can spend hours on a receiving line. Vice President Kamala Harris is almost always in Manolo Blahnik 70 mm heels (about 2.5 inches, a.k.a. mid-height). I think the answer lies in the soul of the matter. Or rather, the sole.

Specifically, chunky, well-insulated rubber soles: the kind that provide support, padding and height and that come attached to gleaming leather uppers, be they loafers or brogues. They can take the form of extra-thick, platform-like soles, lug soles or big, blocky heels, but the effect is to insulate your feet from the concrete sidewalk while also providing some give. And to do so in the form of footwear once favored by Princess Diana in her post-royal phase, footwear with historical associations of substance and seriousness (and, OK, school).

It’s the kind of footwear that has the power of high heels without the pain. It conveys grounded-ness, literally, as well as imaginatively. It’s footwear that works with both pants and skirts of varying lengths and nods to the 1990s redux moment we appear to be experiencing without getting mired in nostalgia.

As Gabriella Karefa-Johnson, the global contributing fashion editor at large of Vogue, who has styled covers with Kamala Harris and Amanda Gorman (among others), said, explaining how she gets dressed in the morning: “Typically I start from the ground up, and if I have something on my feet that feels fit for an occasion, I can feel comfortable anywhere — even if I’m in jeans and a vintage T-shirt.”

While Ms. Karefa-Johnson favors midi-boots for going out (a current favorite: the Maison Margiela Tabi), she said that for daywear, she always comes back to “a chunky-heeled loafer.”

And as far as chunky loafers go, there are a lot of options. Just be sure you choose rubber soles as opposed to wooden ones, which can make walking feel like weight lifting for the leg.

If you want to get technical about it, Paul Andrew, the designer of a namesake shoe line and the former creative director of Ferragamo, noted that “rubber inherently allows flexibility, whereas wood does not bend and support the foot during propulsion. Look for a style with a molded or padded footbed.”

Some good places to start: Franco Sarto, which offers a number of versions; Madden Girl Kassidy heeled loafers; and Caslon Millany loafers. (I am partial to the silver metallic uppers.)

For slightly more expensive pieces, check out Bernardo 1946; Loeffler Randall, which also offers very walkable ankle boot versions; and the Coach loafer heel.

Then, said Mr. Andrew, who summed up the effect as “look at me, but don’t mess with me,” let your feet do the talking.

Your Style Questions, Answered

Every week on Open Thread, Vanessa will answer a reader’s fashion-related question, which you can send to her anytime via email or Twitter. Questions are edited and condensed.

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