As you break out your fall wardrobe, you might see it’s time to replace a pair of beloved boots or upgrade to a new style. And just like with the must-have cozy sweaters of the season, certain styles dominate fall boots this year.
Fall 2023’s biggest boot trends include slouchy over-the-knee boots, chunky combat and moto boots, sleek riding boots and updated Western boots explains influencer Sarah Chiwaya. But it doesn’t matter how stylish a pair of boots is if they aren’t going to remain comfortable throughout each wear. “I always start by looking at brands that I know make quality shoes and then look for trending styles from them,” she says. “It makes a difference when you spend a lot of time on your feet.”
And there’s one thing that all trending boot styles have in common for the season: a shorter heel height than in years past, according to stylist Desiree Miranda. “This is heavily due to women choosing comfort and practicality over anything else,” she says. “The knee-high and Western boot styles all work with lower heel heights because they naturally elongate a woman’s body.”
With so many fall-worthy options this season, we consulted with fashion experts to find the best on-trend boots for comfort and style enthusiasts alike.
Tall boots and knee-high boots
According to Miranda, one of the biggest boot trends you will see this fall is the sleek knee-high style, preferably with a pointy toe. “To obtain the perfect shoe capsule wardrobe, I first suggest opting for straight leg style,” she says, noting that this pair from Lulus nails the straight silhouette along with another big trend: snakeskin. “These are so chic … snakeskin is one of my favorite trends to play around with for fall,” she says. “You can wear a simple all-black or monochromatic look and these boots will be just the right amount of pop to give you that stylist-approved edge.”
“I am a slouchy thigh-high/over-the-knee kind of gal,” influencer Deanna Giulietti says. “The comfiest, stretchiest over-the-knee boots that I like to wear are from Vince Camuto.”
These Torrid heel boots come in extra-wide calf width and are a trusted favorite for fashion influencer Colette Hanna. “I own both the taupe and the black — the heel is comfortable without being overly high and honestly they are one of the few brands that ensure they are wide-calf through the thigh,” she says. “Buy them before they sell out, they're usually the first ones to go every season!”
“To-the-knee boots are always stylish for the fall season and add a chic look to any outfit, especially fall dresses and skirts,” influencer Dana Berez says. Available in five colors appropriate for fall, “these boots have a block heel and unique metal ornament on the side for added detail.”
“When I'm looking at tall boots, I always look for wide-calf options,” Chiwaya says. “These Western boots come in two calf widths and I love the rich color.”
Influencer and CEO Mandy Madden Kelley describes this riding boot as the perfect balance of classic and contemporary design, with the slim buckle strap adding a modern touch to the timeless feel. “The smooth leather complements any outfit, from pants to midi dresses,” she says. “I also love the Naturalizer’s signature Contour+ technology, ensuring maximum comfort and support for all-day wear.”
“Here is a classic straight-leg boot style that will go with relatively everything in your wardrobe,” Miranda says. “This is a great pair to style with mini skirts and short dresses come fall.”
“Lace-up knee-high boots and combat boots are also coming in hot for fall/winter,” says Giulietti. “I just need a boot that zips all the way up and I am good to go — spending 20 minutes lacing up a boot is my nightmare.” She says that if you’re hopping on the trend, she has this pair of zippered lace-up boots and they’re the ones to get.
“Red is another huge trend for fall, and this sleek wide-calf pair is on my radar,” Chiwaya says. These tall, stacked-heel boots have a pointed toe, foam sole insert and whipstitch detailing.
According to Miranda, the Western boot trend is here to stay for the coming season — with good reason. “Western styles are so comfortable due to the classic low heel height and block heel style,” she says. “A white Western boot is a great go-to as your statement piece when putting together uniform outfits. I love this pair for the fall over a light-wash jean and a tan sweater.”
Mid-calf boots
This leather Chelsea boot combines the timeless elegance of a pointed toe with a decidedly Western twist in the form of an angular Cuban heel, explains Kelley. “The covered gore insets add to the sleek aesthetic of the boot, while also providing comfort and a snug fit,” she says. “What I love most about these boots, aside from their architectural design, is that they are incredibly versatile — they can be dressed up or down to suit any occasion, whether it’s a day at the office or a night out on the town.”
These black full-grain leather boots are hand-stitched with a Western pattern and are a must-have for every fall wardrobe, according to Miranda. “The mid-calf style is so flattering on so many different body types and the almond toe shape is sure to be comfortable on all foot sizes,” she says. “Thursday Boots is one of my go-to brands for clients as they have such a great range of year-round boot styles. Secondly, they have some of the best genuine leather on the market for an unbeatable price.”
With a stacked wood heel as well as mixed vegan leather and suede material, these pointed-toe boots are one of Giulietti’s favorite mid-calf options. “Pointy toes are in this year,” she says. “If you are looking for a mid-calf boot that is eye-catching and sleek and simple, I love these mid-calf nude boots from Lulus.”
“For leather, I recommend André Assous because the brand has a great water-resistant leather that holds up to all the slush on the streets of NYC,” Chiwaya says. “I already have a well-loved pair of combat boots from André Assous that I'll be wearing again this year, and I'm also eyeing this new chunky block-heel pair (a great option if you want a nod to the trend without it being overly faddish).”
Giulietti loves “stretchy boots,” especially these square-toe booties with contrasting faux leather and bone ribbed knit. “For me, I have bigger calves, so I am so picky about my boots,” she says. “They need to be able to comfortably fit on my legs. I don’t want to have to cry over a zipper not making it over my calf.” The style also comes in black, camel and black crocodile.
Ankle boots
Hanna personally loves gold hardware or mixed metals on her boots. “They provide an elevated and sleek vibe to any look,” Hanna says. “These boots are so comfortable to walk in — I am able to wear them to work and out at night.”
A kitten heel is one of the biggest trends that Berez is seeing this season. “They add a look of sophistication, but they are also super practical for everyday wear … This kitten-heel boot can be paired with so many different bottoms, and can be worn from the office to evening,” she says. “The heel height provides that versatility to being casual but still dressed up enough.”
Hanna recommends these waterproof shoes, which come in both suede and leather, if you're looking for a clean bootie without laces. “They’re easy to put on and walk right out the door, have enduring quality and are effortlessly chic,” she says. “There's also a beautiful variety of tones available for this season — I love my cognac pair!”
“These ankle boots have a nice block heel, making them comfortable to wear,” says Berez. Plus, they come in four options, including snakeskin. “Snakeskin is also a big trend this fall season, and looks chic in a boot style,” she adds.
Hanna describes these as “a classic Chelsea boot for every fall/winter look in this dream cream tone” and says that she bought two pairs for herself just in case. “I love winter whites, and winter whites are back on trend,” she adds. “I love the material, they are not heavy on the feet at all.”
Kelley says the waterproof finish on these suede and leather boots is a game changer, making them a must-have for anyone who wants to spend more time outdoors this fall. “These boots combine style and practicality, with a sleek leather look that is perfect for any outfit while being built on a chunky platform with sturdy lugs for stability on wet and slippery surfaces,” she says. “Plus, the classic Chelsea boot design adds a touch of timeless elegance to any outfit.”
“A casual staple and very on-trend right now, these lace-up hiker boots give any outfit that bit of edge or ruggedness for fall,” Hanna says. “They are also wide-width and very easy to walk in due to the chunky block heel.”