By Deena Shankar

IF YOU are a woman who works, chances are you have struggled with footwear.

Maybe you’ve commuted in one pair and then changed into another when you got to your desk. Maybe, over the years, you’ve built a collection of not just shoes, but also tiny socks of different shapes and sizes — socks that barely cover your toes, that aren’t supposed to peek out of your shoes but inevitably do, that are like tiny little stockings, or with a glue bit on the back heel to hold them in place. Maybe you’ve stared at the feet of the women you see on the subway or in your office and wondered, “Did she actually walk here in those shoes?” Maybe you, like me, have actually stopped several of these women to ask them that question, and if the answer is, “Yes, these are comfortable enough to walk in and they look good with my professional attire,” followed up with another inquiry: “Who makes them? Would you spell that, please?”

Climbing the male-dominated corporate ladder is hard enough on its own. It’s even worse in bad shoes.

Women looking for the right pair have no shortage of options. The US women’s footwear market was $33.9 billion for the 12 months ending in April 2019, according to the NPD Group/Consumer Tracking Service. The most growth is coming from the sport leisure category — but even fashion, which had been declining, is now leveling out, thanks to those brands incorporating comfort.

So what brand is doing it best?

There is no single answer: For every woman who swears by her Rothy’s, there is another who bemoans the $125 wasted on yet another pair of toe scrunching, back-of-the-ankle-tearing shoes. While some women are willing to go through the pain of breaking in a pair of Everlane Day Gloves, others don’t have the patience. Bloomberg spoke, e-mailed, and DMed on Twitter with dozens of women, including fashion experts, lawyers, journalists, and an array of other professionals.

There were few consensus items, but plenty of passion. Here are some in three broad categories that get rave reviews.

There is a reason that Chanel flats have been so ubiquitous for so long. If you are ready and able to spend $700 on a single pair of shoes, no one style comes more roundly recommended than the lambskin. The supple leather makes them comfortable right away, without the dreaded rubbing that can happen with the fashion house’s other styles and leathers.

For those not looking to spend quite that much money, Atillio Giusti Leombruni (or AGL) also makes a ballerina flat, though some breaking in is to be expected.

If the rounded toe shape isn’t your style, try the pointier-toed Barneys New York Suede & Mesh flats, recommended by Marina Larroude, vice-president and fashion director at Barneys New York. “The mesh of the ballerina is very soft in the feet, super comfortable, and light, especially during the summer time,” she says.

The snakeskin CC Corso Como skimmer is one of Nordstrom’s most popular stylish and comfortable flats, says Kate Bellman, director of Nordstrom’s fashion office, though it’s available in many materials and colors.

No shoe quite says “ready for business” as a loafer does. The Gucci classic menswear style is recommended by Erica Russo, vice-president and fashion director of accessories and beauty at Bloomingdale’s. “I love this style because the leather will give over time, making this a great fit,” she explains. Every Gucci loafer-wearing woman that Bloomberg spoke with praises its immediate comfort as well.

For something a little more fashion-forward, try the Noelle loafers from The Row. “The soft suede makes them really easy wearing, right out of the box,” says Rati Levesque, chief operating officer of luxury consignment site RealReal.

Many women also said they were major fans of the Cole Haan brand, which offers several loafers.

Clogs are not always flats, but they are comfortable enough to have migrated from nurse wear to streetwear and stayed put for some years. They are not suited for long walks, says Adam Farber, owner of comfort-focused, independent shoe store Mark Adrian Shoes in Gloucester, Mass., but they are a good choice for anyone who logs many hours on their feet. Mr. Farber likes Dansko best, but brands such as Swedish Hasbeens, No.6 Store, Nina Z, and Rachel Comey offer a range of colors, styles, and heel heights.

When it comes to shoes, many women don’t realize that, as with the rest of their bodies, sizes can shift.

“Feet change over time; they get larger, wider, and longer,” Mr. Farber says. “It’s really important not to be married to a number.” That means that even a shoe that fits one year might not work the next.

“People are constantly fitting themselves incorrectly, and the fit is almost as important as the structure of the shoe itself,” he continues, recommending that shoppers get fitted by an expert and try everything on in-person as much as possible.

Nordstrom’s Ms. Bellman agrees: “It’s important to know the shape of your arch and work with a certified shoe fitter to identify the best support for your foot.” (The service is complimentary at the retailer.) “Foot pain often comes from improper arch support, but there are many shoes available that provide architectural arch support technology that alleviates discomfort. Lastly, a flexible sole will encourage proper movement and gait.”

The right fit means that there should be a thumbnail’s worth of space between your toe and the front of the shoe, felt by someone else, says Mr. Farber. A little bit of heel slippage at the beginning is to be expected. A snug fit is not the goal.

For those logging the most miles, a slip-on flat is not the right choice. “You want a ‘seatbelt,’ something that’s going to keep the shoe on your foot so you’re not scrunching your toes up to keep the shoe on,” he says. That can cause heel pain known as “plantar fasciitis.”

In addition, he cautions, even the best shoes aren’t necessarily perfect for you right out of the box. Mr. Farber says a good shoe can take as much as a week to break in. Start with an hour on day 1, two or three hours on day 2, and so on.

Remember, most retailers won’t accept the return of a shoe worn outside. So choose your store with its return policy in mind and wear a shoe indoors before you take the leap into the great outdoors.