In 1927, a shoe company in St. Louis launched a women's line called Naturalizer and bet everything on fit. Decades later the brand still describes itself as the one that became known as the shoe with the beautiful fit, and its CEO has claimed Naturalizer was the first to build a shoe on a woman's last. It is a company claim, but I like the instinct: start from the woman's foot, then add the style. It is how I think about comfortable shoes for women in October, when sandals are gone and the day starts at a desk and ends somewhere with stairs. I went deeper on a related idea in Burberry Jacket for Women: Start With the Trench, Then Go Beyond It. I went deeper on a related idea in Burberry Shoes for Women: Boots, Flats, Loafers and Slides.

 

Comfort also has a second origin story. In Frankfurt in 1902, Konrad Birkenstock invented a three-dimensional insole to go with his anatomically shaped last, and called the pair health footwear. His own company's archive admits the idea was ahead of its time: the footbed was not recognized as a remedy until 1914. The idea behind every cushioned shoe since is the same, and loafers are where I would start.

 

In my fashion dreams she is crossing a lobby at 8:55 in the olive suede Stassi tassel loafer from Cole Haan, a quarter inch of heel and a low flat sole, with cropped wool trousers and a gray knit. The black ECCO Modtray penny loafer is the weekday workhorse: a chunky lugged sole and a 1 1/2 inch heel give you some height without the strain. The SAS slip-on moc is softer and flatter, at 1 inch, and the Birdies Starling 20 is the smoking-slipper take at 3/4 inch. If you want a little more polish, the Coach Leah has logo hardware on a lug sole.

 

Practical tip: bend the shoe before you buy it. A loafer should flex at the ball of the foot, not in the middle of the arch, and your heel should stay put when you walk across the room.

Podiatrists are blunt about flats: thin soles and no support are where the fatigue starts. One podiatrist's advice is to choose flats with firm heel counters and padded insoles, and I treat that as the checklist for every pair here.

 

The Rothy's Daily Flat is a black knit with a round toe, flexible and machine washable, which makes it the one I would keep under the desk. The Birdies Hummingbird in noir is nappa leather with a small bow, and the ECCO Margot has the same bow idea on a round toe with a quarter inch of heel. For a softer palette, the Cole Haan Go-to Tova in sesame suede with a cream grosgrain bow reads like spring in the middle of fall. The SAS Radiant Comfort in hazel has an elastic topline and a white sole, so it stays on without gripping. The Naturalizer Kelly Ballet brings the 1927 brand back into the conversation with a pointed-round toe, and the Tory Burch Reva Travel adds a gold Double T medallion to an elastic topline.

 

Pair them with straight denim that stops at the ankle, or with a midi skirt and opaque tights. In the fitting room, press your thumb into the footbed: you want it to push back a little, not collapse. Then stand on one foot for ten seconds and see whether the heel slips.

 

What I would skip: a flat that only looks padded. If the sole bends in half like paper, it is a slipper with a bow.

The number to know is two. A podiatrist's guidance is to choose heels under 2 inches with a wide toe box and a cushioned insole, and a block heel gives you a wider base and more stability than a stiletto ever will.

 

Shop by the numbers. The Cole Haan Go-To Block Heel pump in black leather, at 1 3/4 inches with a rounded cap toe, is the easy office answer. The Nella in black suede is a slingback at 1 1/2 inches. The Vagabond Ilona in brown has a pointed toe and an angular low block at 1 6/7 inches, and the Sofft Sandra in tobacco has the same height with a softer, more forgiving shape. The Rothy's Mary Jane Heel in black knit is right at 2 inches. The Franco Sarto Racer in navy and the Marc Joseph Midtown in black patent sit just above 2 inches, so I would keep those for shorter days. The LifeStride Mary Jane with double straps is the one to wear when you want the strap to hold you in place.

 

Try this at home: walk down a staircase in them, then up. If your toes jam forward on the way down, the toe box is too tight or the heel is too tall for you.

 

What I would skip: pointed toes in a half size too small. The heel gets blamed, but the toe box is usually the real problem.

Boots are where comfort and weather meet, and the Chelsea is the easiest shape to live in. The elastic gores let your foot move, and a lug or wedge sole gives your step some spring.

 

The Born Cove in gray full grain leather has a 1 1/4 inch heel and the Born Verona in black is on a chunky lug sole. The ECCO Dress Classic 35 in mink is the quiet one, a tan Chelsea with a stacked low block heel. The Cole Haan Zerogrand Rexanna in dark chocolate sits on a cream wedge sole and is waterproof, which matters in a wet commute. The Sam Edelman Laguna has tonal elastic panels, and the Clarks Orinoco 3 is a side-zip waterproof boot for days when I would not want to fiddle with pull tabs. The Naturalizer Juni in black water repellant leather has a lug block heel at 2 1/2 inches, and the Cole Haan Haddie has a back zip and a low block heel.

 

Wear them with tights and a knit skirt, or with straight jeans that skim the shaft. Check the ankle: your heel should not lift when you walk, and the shaft should not dig in when you flex.

 

What I would skip: a boot that needs breaking in. A good shoe should fit properly from new, according to the NHS leaflet I read, and a boot is not the place to test your patience.

The Boston clog arrived at Birkenstock in 1976 and was an immediate hit with medical professionals and chefs who needed work shoes with toe protection. A catwalk moment followed in 1987, when Issey Miyake showed it. I think that is the right way to read clogs: working shoes that fashion caught up with.

 

Dansko's Professional Clog in chocolate is the working classic, with an oiled leather upper and a stitched edge, plus an anatomically contoured midsole, a roomy reinforced toe box and an anti-fatigue rocker bottom. The Sonja in black oiled leather has a contoured footbed and a 2 inch heel. The Rothy's Casual Clog in dove is a woven knit with a soft footbed, the lightest thing in the group. The Coach Archival Buckle in black suede has a gold logo buckle, and the Kate Spade Cosima in light fawn is a lug platform mule with a slingback strap. The FitFlop Shuv has a cushioned sole and a cream toe cap, the ECCO Soft 60 slide clog is the simplest, and the Fleks Noleta is a black wool felt clog with a molded footbed, my pick for a cold apartment.

 

A word on the APMA Seal of Acceptance. It is a recognition, not an endorsement, and it is granted after a review panel decides a shoe allows normal foot function and promotes foot health. It runs up to three years, so look for the date.

 

What I would skip: a backless mule with no footbed to speak of, if you plan to walk across town.

I would shop in this order. Measure at the end of the day, when feet are at their largest, then start with the loafer, because it works for the most days, and add one flat that has a firm heel counter and a real footbed.

 

Next, pick a block heel under 2 inches for the nights you want height, and a Chelsea or a clog for weather. Rotate them: no pair does best when worn five days in a row.

 

Konrad Birkenstock spent years on one idea, that a shoe should start with the foot. It is a good rule for a closet, too, and it still beats any trend.