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Fashionable, Feet-Friendly Shoes and Boots for Fall

Step out in style in flats, boots and heels that feel as good as they look


spinner image a woman looking at a display of boots and purses while shopping in a store
miljko/Getty Images

Shoe shopping is always a good time. No anxiety about weight or bulges, just lots of mood-boosting cheer. Even a pair of fresh $35 ballet flats can make grownup women feel more powerful, confident and sexy as a supermodel. But there’s one hitch … foot amnesia. That’s when in the bliss of the moment all our bunions and blisters, sore soles and swelling ankles, corns and calluses fade away. That is, until we actually wear the new shoes and memories of Band-Aids come flooding back. Is this year’s crop of fashionable shoes and boots really feet-friendly? The answer is yes if you tread carefully. Here are the ones to look for:

1. Calf-loving tall boots

Let’s start at the top now that knee-high boots have returned to A-list status. There’s no debate about their fashion creds — tall boots look posh worn with midi dresses and over leggings or skinny jeans (yes, this is exactly why you saved the latter). So, here’s the one hitch. Those with generous calves and/or thick ankles and anyone with swelling or circulatory issues can feel squeezed by the leg-hugging fit and have difficulty getting them on and off with ease. Wide-calf boots have been around for years, but they often looked frumpy compared to their slimmer sisters. This year, style and comfort have teamed up with stretchier faux leathers and suedes, flexible gores at the sides or rear, full-length zippers and specific circumference information for consumers. This is important since a 16+-inch “wide” boot is very different from one that appears wide online but may be only 14 inches. Try these updates: a riding boot with low block heels like the LifeStride Brooks Wide Calf Boot in Black ($90, dsw.com/en/us), a sleek kitten heel style like the Naturalizer Deesha Wide Calf Tall Dress Boots in Cafe Brown Suede or Cocoa Brown Suede ($186, macys.com) or a Western-inspired style like the Frye and Co. Women’s Selah Stacked Heel Cowboy Boots in Cognac, Cream and Black ($75, jcpenney.com). Still concerned about calf fit? Try the DuoBoots Haltham Standard Knee High Boots in Black Leather ($295, duoboots.com/en-us), a basic but fashionable flat knee-high boot that comes in eight calf widths.

spinner image Frye and Co. Women’s Selah Stacked Heel Cowboy Boots in Cream; Naturalizer Deesha Wide Calf Tall Dress Boots in Cafe Brown Suede; DuoBoots Haltham Standard Knee High Boots in Black Leather; LifeStride Brooks Wide Calf Boot in Black
(Left to right) Frye and Co. Women’s Selah Stacked Heel Cowboy Boots in Cream; Naturalizer Deesha Wide Calf Tall Dress Boots in Cafe Brown Suede; DuoBoots Haltham Standard Knee High Boots in Black Leather; LifeStride Brooks Wide Calf Boot in Black
JCPenney; Macy's; DuoBoots; DSW
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2. Pillow-y loafers

You can’t go wrong with loafers. This once-preppy shoe is now a genuine fashionista. Though many loafers appear sturdy, they’re not problem-free. They often require a “break-in” period to soften the topline and heel, and drugstore inserts to help mature bony feet feel comfy. Not anymore if you choose carefully. Styles with modified lug soles like the Madewell The Bradley Lugsole Loafer in Leather in True Black ($158, madewell.com) and Dr. Scholl’s Women’s Nice Day Loafers in Black/Black Faux Leather ($70, macys.com) have the crucial cushioned footbeds and ridged soles for traction (despite what you may have heard, lug soles are still “in”). For a more refined or polished look, try soft supple loafers with delicately squared-toes and hardware details at the instep like the A New Day Women’s Laurel Loafer Flats in Black or Light Taupe ($33, target.com) or the New York & Company Women’s Harleigh Square Toe Loafers in Black or Cognac ($60, jcpenney.com).

spinner image A New Day Women’s Laurel Loafer Flats in Black; Madewell The Bradley Lugsole Loafer in Leather in True Black; New York & Company Women’s Harleigh Square Toe Loafers in Black; Dr. Scholl’s Women’s Nice Day Loafers in Black/Black Faux Leather
(Clockwise from top left) A New Day Women’s Laurel Loafer Flats in Black; Madewell The Bradley Lugsole Loafer in Leather in True Black; New York & Company Women’s Harleigh Square Toe Loafers in Black; Dr. Scholl’s Women’s Nice Day Loafers in Black/Black Faux Leather
Target; Madewell; JCPenney; Macy's

3. Supportive ballet flats

Women wear ballet flats to channel their inner Audrey Hepburn and feel feminine. Simple, streamlined ballet flats are a must-have, and despite our love for them, they often don’t love our feet back. They can be flimsy and thin-soled with no arch support or shock absorption, so toes must do more “grip” work resulting in plantar fasciitis and an increase in corns and calluses. This fall many flats feature pointed toes, which are not exactly helping bunions and can contribute to piggies curling into “hammertoe” formation. The best solution is to get serious about foot health and choose ballet flats with a supportive insole and a square or oval toe like the Old Navy Faux Leather Ballet Flats for Women in Tan, Blackjack and Gray ($25, oldnavy.gap.com), Gentle Souls by Kenneth Cole Women’s Mavis Slip On Ballet Flats in Pewter or Black ($169, bloomingdales.com) and Franco Sarto Flexa Amaya Flats in Black Leather, Beige Leather or Shocking Pink Leather ($130, macys.com).

spinner image Franco Sarto Flexa Amaya Flats in Black Leather; Old Navy Faux Leather Ballet Flats for Women in Tan; Gentle Souls by Kenneth Cole Women’s Mavis Slip On Ballet Flats in Pewter
(Clockwise from top left) Franco Sarto Flexa Amaya Flats in Black Leather; Old Navy Faux Leather Ballet Flats for Women in Tan; Gentle Souls by Kenneth Cole Women’s Mavis Slip On Ballet Flats in Pewter
Macy's; Old Navy; Bloomingdale's
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4. Comfortable ankle boots

Whether you call them Chelsea boots, ankle boots or booties, these shorties are indispensable for cold weather. The big draw is how easily they slip bulge-free under our pants and jeans with none of the tall boot concerns. However, many ankle boots feel rigid, and lack the padding, elastic gores and rear pull-tab for easy on and off. It takes some homework, but try the superpolished Everlane The City Boot in Dark Brown Suede ($275, everlane.com) with square toe and side zip, the edgy Dream Pairs Women’s Chelsea Ankle Booties in Black/Pu ($35, amazon.com) with lug sole for extra traction or the trendy Lisa Vicky Steady Western Bootie for Women in Black, Tan Camel or Stone ($100, nordstrom.com) for a subtle twist. And here’s another reason to choose only ankle boots with a heel tab — it prevents your socks from bunching up as you slip them on.

spinner image Everlane The City Boot in Dark Brown Suede; Dream Pairs Women’s Chelsea Ankle Booties in Black/Pu; Lisa Vicky Steady Western Bootie for Women in Tan Camel
(Left to right) Everlane The City Boot in Dark Brown Suede; Dream Pairs Women’s Chelsea Ankle Booties in Black/Pu; Lisa Vicky Steady Western Bootie for Women in Tan Camel
Everlane; Amazon; Nordstrom
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5. Walkable pumps and slingbacks

Just when many women had given up high heels forever, block-heel pumps and slingbacks have snuck back in style. While some block heels are still way too high, putting stiletto-like pressure on the balls of your feet, others are too pointy, wreaking extra havoc on toes. But with a little careful editing, you can find fashionable pumps and slingbacks with heels no more than 2 inches in height and gently rounded toes that are feet-friendly. Go ahead and try the Ann Taylor Tweed Cap Toe Block Heel Slingback Pumps in Black Multi ($148, anntaylor.com), the Vaneli Aliz Slingback Pump for Women in Pudding Leather ($165, nordstrom.com), the J.Crew Layla Slingback Mary Jane Heels in Spazzolato Leather in Black ($198, jcrew.com) and the Tory Burch Women’s Bow Ballet High Heel Pumps in Shell Pink/Black or Perfect Black ($298, bloomingdales.com).

spinner image Ann Taylor Tweed Cap Toe Block Heel Slingback Pumps in Black Multi; J.Crew Layla Slingback Mary Jane Heels in Spazzolato Leather in Black; Tory Burch Women’s Bow Ballet High Heel Pumps in Shell Pink/Black; Vaneli Aliz Slingback Pump for Women in Pudding Leather
(Clockwise from top left) Ann Taylor Tweed Cap Toe Block Heel Slingback Pumps in Black Multi; J.Crew Layla Slingback Mary Jane Heels in Spazzolato Leather in Black; Tory Burch Women’s Bow Ballet High Heel Pumps in Shell Pink/Black; Vaneli Aliz Slingback Pump for Women in Pudding Leather
Ann Taylor; J.Crew; Bloomingdale's; Nordstrom

6. Healthy rain boots

Your rugged snow boots and rubber Wellies are fine for shoveling the driveway, but how about when you go to work or out for the evening in a downpour? Rainy day boots that mimic the leather ones and look stylish enough for your good black pants or a midi sweater dress are a major trend. But even those that protect feet adequately from puddles are not without problems. As a stylist and personal shopper, I hear plenty of complaints from clients about sore heels and rubbed-raw anklebones, blisters, sweaty moist feet, a poor fit and lack of support. There are some pretty terrific problem-solving options like the Cougar Firenze Women’s Boot in Black All Over ($75, amazon.com) with absorbent knit lining, cushioned foam footbed and padded outsole, the Bogs Women’s Sweetpea Boots in Black ($85, zappos.com), cut lower at the ankle with a sweat-wicking liner and the Merry People Bobbi Rain Boot in Alpine Green & Black ($130, merrypeople.com) with built-in arch support, front and rear pull tabs, and neoprene lining for comfort. And it comes in 15 colors. Those tired of wide, clunky, taller rain boots can try the Ilse Jacobsen Rubber Boot for Women in Black ($230, nordstrom.com), lavish-looking knee-highs designed for wide calves with an adjustable lace-up front that accommodates calves from 15½ to 21½ inches. Make a splash!

spinner image Ilse Jacobsen Rubber Boot for Women in Black; Cougar Firenze Women’s Boot in Black All Over; Merry People Bobbi Rain Boot in Alpine Green & Black; Bogs Women’s Sweetpea Boots in Black
(Clockwise from left) Ilse Jacobsen Rubber Boot for Women in Black; Cougar Firenze Women’s Boot in Black All Over; Merry People Bobbi Rain Boot in Alpine Green & Black; Bogs Women’s Sweetpea Boots in Black
Nordstrom; Amazon; Merry People; Zappos

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