Ask the Strategist: A Comfy Shoe Bonanza

In our advice column, “Ask the Strategist,” we answer your most burning shopping questions by surveying friends, calling up experts, and drawing on our own personal experience. Today, we’re answering reader questions about ultracomfortable women’s dress shoes, walking shoes for a trip to Japan, and the glasses Monk wears in American Fiction. If you want a chance to get expert advice from our team, send us an email at strategist@nymag.com with the subject “Ask the Strategist.” We’re here to help — and you may see your question answered in a future newsletter.

“I am going to Japan for vacation and I need a pair of sneakers or sneaker-minded shoes that: I can comfortably walk a lot in, look good with both jeans and skirts/dresses, have a bit of chicness about them, and are mainly one neutral color. I’m not looking to spend more than $100 to $150 if I can help it.”

My first recommendation is a pair of New Balance 993s because of their comfortable sole (your feet will thank you after walking all over Japan) and how they pair well with a ton of different outfits. Plus, they’re available in wide sizing. (You can’t go wrong with any shoes in the 990 stable — they come in fun, subtle colors too.) For something chicer, I’d point you to a pair of Onitsuka Tiger 66s. They have a thinner sole, so they definitely won’t have the same support as the New Balance, but their slim profile and simple colorways seem to fit the bill. —Jeremy Rellosa, writer

“I’m going to Japan in the fall and I need a very specific kind of shoe: something a little dressier than a Skechers for big cities that are easy to slip on and off, comfortable for walking, and less than $200. Do such shoes exist?”

I’m into the orthopedic Arcopedicos that writer Misty White Siddell found in Milan — so ugly-cute, they’re to flats what pugs are to dogs. These knitted Camper ballerinas are a cousin. There’s the wool version of the Merrells designer Sandy Liang wore on her wedding day. And while we’re on Merrells, Strategist senior editor Hilary Reid recently caught these suede ones (that come in wide widths) with a back stripe on the feet of a woman shopping at a bridal salon. (P.S. I’m hoping you two somehow run into each other on the streets of Japan in your Strategist-recommended shoes.) —Ambar Pardilla, writer

“What is the best lightweight walking shoe with great cushioning for women over 70?” 

When it comes to cushioned walking shoes, it’s hard to beat Hokas. I’d recommend the Hoka Bondi 8. It has a ton of foam cushioning underfoot, which means it should be easy on your joints, especially your knees. The Hoka Clifton 9 is also a great walking shoe that I frequently recommend, and it’s an ounce lighter than the Bondi 8, but it has slightly less cushioning. My mom, who is in her 60s and just recovered from knee-replacement surgery, swears by her Oofos slide-on shoes, which have generous cushioning and are especially easy on her knees. —Jeremy Rellosa, writer

“I am a 59-year-old woman who is having a terrible time finding appropriate shoes that will provide support but will also be classic/stylish for my new job working in a high-end luxury-goods store. In other words, I am on my feet up to eight hours a day! I would love to find a black leather shoe that is not a flat or a ballet shoe. Please help.”

An orthotic loafer with some subtle lift, such as these from ABEO footwear, should fit the bill nicely. It has a classic, understated silhouette and features an orthotic footbed, arch and heel support, and a fairly spacious toe box, so hopefully it should be comfortable enough to stand in for hours. —Kitty Gao, writer

“I’m looking for stylish, ultracomfortable women’s dress shoes (not flats or heels) to wear with suits in court when I’m going to be on my feet all day. Preferably they’d have a wide toe box. I’ve been looking for years without any definite success. Please help.” 

Danish shoe brand Duckfeet is known for its wide toe box that allows your feet to splay naturally. To pair with a suit, I’d suggest a loafer or an oxford, such as its Fyn, Falster, or Jylland styles — you can stick with staid black or show a little personality with its wide range of color options. I can also personally vouch for the brand, as I own a pair of its boots and have found them to be comfortably accommodating of my wide, bunion-afflicted feet. —Kitty Gao, writer

Plus: “Hi! I watched American Fiction yesterday and loved the glasses Monk wears. Could you tell me the designer and model?”

Those are pretty ideal tortoiseshell eyeglasses, aren’t they? To find out the exact frames, I called up Rudy Mance, the costume designer for American Fiction. As there often is with finding the perfect pair of glasses, there was a hunt involved. Jeffrey Wright tried about ten pairs of glasses from the prop department before Wright and Mance took things into their own hands. “The night before we started filming, Jeffrey and I split up and went to different malls in Boston and sent each other pictures of the glasses we found,” says Mance. The winning pair was Persol’s PO3143V frames in “Havana,” a model that satisfied the “classic and somewhat bookish” look they wanted for Wright’s role as Monk. —Hilary Reid, senior editor