I embraced the orthopedic life early, at the relatively tender, at least for this kind of thing, age of 32. After a painful neuroma (a.k.a. a pinched nerve), caused by wearing shoes a half-size too small for the better part of a decade, prematurely consigned me to a life of supportive footwear, I jettisoned my beloved shoe collection and never looked back.
Rather than wade through a sea of footwear clearly designed for the over-60 set in search of some halfway-sexy options, however, I decided to run entirely in the other direction, selecting what may be the most geriatric-looking shoe in recorded human history: the Siesta by SAS Shoes. I figured if I was going to be forced into a category of shoes I had no interest in, I might as well lean into their clownish aspect by choosing the most aggressively orthopedic-looking shoes possible. (I have also long harbored a fondness for grandma-adjacent clothing such as nightgowns and novelty cardigans, so admittedly, these were not too far out of my wheelhouse.)
The Siesta is, of course, the puffy, wrinkle-toed wedge most frequently found in nursing homes and thrift stores, freshly donated by relatives of the recently deceased. Less preppy than a Clarks Wallabee and more laid-back than a nursing shoe, Siestas bear an uncanny resemblance to a naked mole rat. Available in colors that range from beige to dark beige, as well as black and white, they’re the perfect shoes for a brisk indoor walk around your local mall or for playing a game of bridge. In all my years of thrifting, I would always briefly think What if? every time I came across a pair, but it wasn’t an impulse I took seriously until I was forced to cross the orthopedic delta.
Founded in 1976, SAS Shoes specializes in footwear for people with foot issues like plantar fasciitis, arthritis, and diabetes — basically, any medical condition my friend Melissa refers to as “ouchie footsie.” According to the company’s website, “approximately 80 different skilled pairs of hands are carefully constructing and inspecting each shoe to make sure the SAS shoes you choose are the best-made pair of footwear in your closet.” Their comfort is due to both their pleasantly bouncy shock-absorbent soles and their intensely cushioned insoles. Each style comes in five widths — slim, narrow, medium, wide, and double wide — to ensure the breadth of one’s foot is fully accounted for.
I purchased my first pair last April in the classic putty shade (it’s technically called “bone”) and have worn them constantly ever since, channeling everything from a severe-yet-chic art collector when I wear them with a structured black dress to a casual Brooklyn errand mom when I pair them with jeans, a breezy button-down, and a baseball cap. They’re the first thing I pack for any trip, and I know I can comfortably wear them on days when the pedometer hits 20,000 steps. To me, they’re essentially interchangeable with sneakers. Anything an Adidas Samba can do, a Siesta can do better.
After a year with my beloved Siestas, I wanted to expand my repertoire. I was interested in the Bravo, a passable dupe of Chanel’s chunky dad sandals, or these modest mary janes, but I ultimately decided to test-drive the most practical (for me) options: the Simplify loafer and the Duo sandals. From far away, the loafers look virtually indistinguishable from their crisp preppy cousins, combining the thick sole of Belgian Shoes with the moccasin-style toe of Sebago or G.H. Bass. They feature invisible stitching and a gently pointed almond toe; the only visual suggestion that they’re manufactured for broken feet is in the sole, which is made of a soft, rubbery material instead of a less-forgiving leather. Wearing them feels a bit like having tiny ottomans strapped to my feet. I can almost guarantee I will never buy another brand of loafers ever again. They come in a range of colors, and I’ve already singled out the gentle metallic “pearl bone” and vibrant cherry-red colorways as my next purchases from the brand.
If you want to look like the kind of person who ties a cashmere sweater over their shoulders while wearing a starched white button-down shirt with a blowout and pearls, then please note I am gesturing discreetly in the direction of this shoe.
The Duo sandals feature dainty cutouts on the strap and exude a playful jeunesse exemplified by the character Miss Honey from the ’90s film version of Matilda. They remind me a bit of Salt Water Sandals in the sense that they are both ageless and timeless. Their classic look could plausibly be worn by kindergarteners and kindergarten teachers alike. When I showed them off to a friend, she exclaimed, “I love them,” in a not entirely convincing way. However, I’ve been clomping in them nonstop since they arrived, enjoying the pleasant sensation of padding around on two giant foot-size marshmallows.
Some Other Orthopedic-ish Shoes the Strategist Loves
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