
For those of us who love fall fashion as much as we adore the crisp weather, crunchy leaves and warm beverages, it’s nearly impossible to resist the shopping itch that also accompanies the arrival of the season. I find shoe shopping practically irresistible year-round, and that urge only intensifies in the fall.
There’s just no denying that autumnal shoes are the absolute peak of footwear styles. It’s the perfect time to indulge in lush fabrications like leather and suede — and the weather is hopefully mild enough to enjoy a range of silhouettes, from boots to flats and loafers and everything in between.
In an effort to find the perfect fall shoes, we tapped incredibly stylish women over 40 to share their must-have favorite shoes, and their answers didn’t disappoint. Keep reading and snag a pair of these chic kicks to enjoy all season long. It’s the easiest way to elevate an outfit and invest in classic footwear you’ll never regret.
A pair of comfortable, designer-doppelganger boots (40% off list price)
Senior shopping writer Lourdes Avila Uribe says, "Anytime I want to add a hint of edge to my outfit, or simply want to keep my feet warm and cozy, I wear these boots. When I laid eyes on Steve Madden’s Jones black leather boots, I knew they’d scratch the itch that The Row’s leather ankle boots have been giving me for the past year. These sleek and devastatingly cool ankle boots boast a black leather construction, oversized and elevated sole and an unexpected front closure that puts the zipper’s functionality front and center."
Check out the rest of Uribe's review here. The boots now available in a range of colors in sizes 5-14.
A pair of soft, suede shoes that are perfect for long walks
Coming in right at the top of our price range are these devastatingly comfortable, ultra-practical and classic Clarks Wallabees shoes. They're currently having a moment with It Girls around the world, and I live in them as soon as temperatures cool down. They're surprisingly easy to style, dress up or down and I can walk for miles while wearing them. I was skeptical when I first purchased them, but I am now a full-on convert. These shoes are incredibly versatile. Everyone needs a pair in their closet rotation.
HuffPost shopping managing editor Emily Ruane also owns a pair. She shared, "They're extremely lightweight and feel like wearing nothing — I can walk and stand in them for hours (which I've done on plenty of occasions). I also love that they look just a wee bit more polished than a sneaker or similarly casual shoe. They're a unicorn in the footwear world, IMHO!"
I have them in black, and you can get them in a wide range of colors in sizes 6-10.
The bestselling, ultra-comfy Dansko "Professional" clog
Ruane frequently rocks this classic style of Danskos to the HuffPost office, saying they're ideal for walking, commuting and riding her bike all over New York. She's worn them through multiple pregnancies, rain storms and more formal events where high heels were just not going to happen.
"They're the kind of shoe that I never think about when I have them on," she said. "When I am wearing them, my feel feel simultaneously completely supported and like I'm wearing nothing. I also like wearing them in inclement weather because they have the slightest platform, which can help when navigating subway puddles and the like."
Ruane says she wears these Danskos with or without socks and finds even the dressier styles to be pretty slip-proof. The darker hues and patterns are easy to dress up for formal events, while some of the more vibrant and whimsical options are great for errands, weekends or fun days with kids.
If you're looking for clogs to wear to work, podiatrist Dr. Saylee Tulpule recommends something with a closed back for additional support as you're moving. In previous reporting, Jacquelyn Coles Bielich, a registered nurse and clinical specialist at Medtronic, in Pittsburgh, Pennsylvania said this style is the only thing she'll wear on her 12-hour shifts.
This style is available in women's sizes 5-15 and in wide and narrow sizes.
A pair of simple, everyday penny loafers
These Spring Step loafers are incredibly similar to the Isabel Marant moccasin-style loafers I have been living in for several years and are unfortunately no longer available. Available in sizes 5.5-11, these timeless leather loafers are soft, with a cushioned insole that provides plenty of support and grippy rubber outsoles that will keep you steady on your feet.
A pair of cozy classics from Ugg
Certified tea blender, consultant, model and jewelry designer JoAni Johnson said, "At my age, or as I say 'level', when choosing a shoe, comfort is the prime consideration. Quality and style are next up in my decision-making. I generally pick colors and patterns that have sustainability both in quality and style. My ever-present go-to is a classic Ugg. It's a staple; always comfortable and can be styled in many ways."
The price on the classic micro style is just right, and it's a deliciously cozy and comfy indoor-outdoor shoe that will keep your feet toasty all fall and winter. You can get it in a few colors in the brand's signature suede and sheepskin fabrication in sizes 5-12.
A pair of supportive flats
"Classics, like a ballet flat, will never go out of style," said Johnson. She added, "In my former career, I always carried a spare pair in my briefcase to give my legs a rest during days of long city walking. I've now amassed a collection of flats over the years, so I have quite the colour selection!"
Personally, I cannot live without my Vivaia Margot flats. From the moment I stepped into a pair of Vivaia flats, I’ve been delighted by how fun, kicky and devastatingly comfy these shoes are. Available in a shocking number of colors and patterns, these truly lightweight flats have a square toe, a V-cut upper silhouette and soft, flexible and subtly ribbed fabric made from recycled plastic bottles. I generally lean towards leather flats and was wary that the fabric would make the shoes look and feel cheap or basic, but it couldn’t be further from the truth.
The square toe feels edgy without being too aggressive, and the v-shape adds a some unexpected of visual interest. Best of all, the springy insole and sturdy rubber outer sole make them great for long walks or days spent standing. You can check out the rest of my review of these fabulous shoes here.
A pair of comfy, packable loafers from Vionic
My mother, Maria, has been raving about these "soft and comfortable" Vionic loafers. She loves that they can be worn with or without socks, and thinks they're the perfect everyday shoe. She also noted that thanks to the unique collapsible construction, they're bendable and easy to pack, making them ideal for travel. They're available in a range of colors (she has the sand suede hue pictured here) in sizes 5-13.
A pair of designer-lookalike Mary Jane shoes
If you prefer a Mary Jane-style flat, then you can't skip over this timeless beauty from Sam Edelman. They're strikingly similar to The Row's high-end doppelgangers, at a much more reasonable price point. They are the ultimate ladylike shoes, and I've had my eye on these for many seasons. It's finally time to pull the trigger. They're available in a range of colors and patterns, including this wildly tempting animal print, in sizes 5-12.
A pair of sneaker-Oxford hybrids
According to HuffPost editorial director Kristen Aiken, these shoes are as versatile as they are comfortable. "I already own at least five pairs of Cole Haan Zerogrand oxfords — most of them in suede — but this 'Stitchlite' material feels like you're wearing nothing but a sock (plus some support)," she said. They're available in a few different colors, but the colorway pictured here feels like the least sneaker-like option.
"Zerogrands are already super lightweight and built with the support of a sneaker, but the Stitchlite material is so comfy that despite considering myself an expert at acquiring blisters, they've never given me one. They're great if you work in an office because they look professional, but feel like you're getting away with something," Aiken added.
A pair of playful sneakerinas
You'll have to forgive me for going $9 overbudget, but I can't leave these delightful sneakerinas off the list. The silhouette of the season is made even better with an ultra-comfy construction and customizable ribbons. They’re shockingly wearable, with a unique look that isn’t alienating to those of us who want to participate in a fun footwear trend without looking flashy or eccentric.
These shoes are available in two styles, the Cristina (a square-toe silhouette) and the Yanka, which has a rounded toe and exposes more of the foot. Both feature Vivaia’s triple-sole construction (that one reviewer described as “comfortable BEYOND belief”) and come with two types of shoelaces so you can customize your look. The outer soles are designed to be sturdy and provide plenty of grip and stability. One reviewer even noted that they were so comfy, she “highly recommended for recovering from surgery.”
A pair of chunky platform penny loafers
Sacha Strebe, executive director at Eyeswoon, is known across the internet for her impeccable taste in clothes. If she's recommending something, I'm definitely adding it to my cart. "I love a penny loafer for fall, and I can’t wait to step into the new season in this deep burgundy shade. The platform style gives some height to elevate any casual outfit. I like to style these with some vintage Levi's, ankle socks and a sheer top," she told HuffPost.
You can get these in sizes 5-11, but don't wait too long, because at this price, these beauties are going to get snapped up quickly.
A pair of sophisticated Mary Janes
Erica Kim, also known as @ahistoryofarchitecture on Instagram, has an incredibly fabulous sense of style. She told HuffPost, "As someone who walks and bikes a lot in the city, I need comfortable closed-toe shoes that can go the extra mile. I used to wear cotton Mary Janes from Chinatown; they were basically slippers and so cute, but they weren’t that comfortable. Small Lot in Vancouver makes a hand-dyed organic cotton version with a natural rubber sole and antique brass buckle. They are surprisingly supportive and work well with lightweight wool socks as the temperature falls. I wear mine with skirts and dresses, and sometimes I channel beatnik Audrey Hepburn with a turtleneck and narrow-leg pants." You can get them in a few different colors in sizes 5-11, though they're flying off the shelves.
If you can't find your size, you might want to give these similar Tuckernucks a look. Or if, like me, you're intrigued by the European cool-girl look of Vibi Venezia shoes, it might be time to succumb to the allure.
A pair of ankle boots with a cowboy flair
"I love a cowboy heel boot," declared Strebe. "This feels reminiscent of the famous Bottega Venetta Lean boot but a fraction of the cost. I would wear these to toughen up a slip dress or a lace skirt with a white tee. Also looks great with jeans!"
Available in sizes 5-11, these sophisticated boots look much more expensive than they actually are.













