The Fall Boots Worth Your Money and Your Closet Space
From $1,000 designer splurges to styles under $100.
I'm a big fan of boots. While some women choose a designer handbag or a heritage watch as their first major fashion investment; I went with a pair of Khaite knee-high boots in sleek black leather with a slim strap and buckle around the calf. Over the past week, I’ve been researching fall 2025 boot trends as a detective would follow a lead, analyzing roughly 200 runway shows to distinguish between Burberry’s equestrian styles and Gabriela Hearst’s mid-calf cowboy boots. This week, I’m focusing on every fall boot I personally want to buy, from under-$200 pairs from Free People to the splurges I'm considering from Toteme for my Fashion Week looks.
First on my shopping list: Western-style codes were a major theme in fall 2025’s shoe trends, appearing as Cowboy Carter-worthy ankle boots and steel-tipped suede boots that are stylish enough for in-office work outfits. Also to note was the resurgence of 2010s-era sock boots, which I’m preemptively crowning as the most unexpected, underdog shoe trend of fall ‘25. After the return of bandage dresses, now we see body-con footwear, starting with boots that fit like a glove and resemble leather stockings.
Ahead, discover a more comprehensive breakdown on the top trending boots worth inviting into your fall 2025 rotation, hand-picked by a bona fide, capital-B Boot Person who has logged her 10,000 hours of expertise.
Fall 2025's Best Boots at a Glance
- The Best Riding Boot: Tory Burch Turnlock Riding Boots, $600
- The Best Moto Boot: Frye 'Harness 12R' Leather Boot, $498
- The Best Western Boot: Sam Edelman West Boot, $195
- The Best Sock Boot: Tony Bianco Margot Boot, $250
- The Best Snakeskin Boot: Schutz Dellia 65mm Snake-Embossed Leather Boots, $129
- The Best Slouchy Boot: Free People Sway Low Slouch Boot, $188
When it comes to the best moto boots, this Free People pair has all the right elements, from the silver hardware harness to pre-worn-in leather.
I can already picture styling these sleek $250 sock boots (look at that curved heel!) with wide-legged trousers and a cinched black blazer.
I'm embracing the outdoorsy English countryside style this fall, starting with a barn jacket and ending with Tory Burch's luxurious riding boots.
The classic elastic-side Chelsea boot makes a comeback every fall. I like how this Polo Ralph Lauren adds a Western touch to the signature autumn shoe.
Schutz's knee-high boot features rich off-white snakeskin for a bold statement. I'd pair this reptile-inspired knee-high with a fall dress made from dark wool blend.
This caramel-colored suede boot by Free People with a practical two-inch block heel is a shoe I know I can wear all around Manhattan, from Marie Claire's midtown office to a dinner downtown.
When I'm truly feeling a yeehaw spirit, these Sam Edelman cow print boots fulfill my cowgirl dreams.
There is something incredibly attractive about a sharply pointed-toe boot—especially when it's crafted in a rich, deep chocolate brown.
Pairing a dark floral boho blouse with indigo jeans (a top fall denim trend, by the way), these Banana Republic brown suede knee-high boots create a classic fall look.
There's a strong reason why fashion enthusiasts swear by Frye's harness boots. The moto-inspired and equestrian style easily pairs with various outfits, such as a lace-trimmed slip skirt or a more preppy look with tailored Bermuda shorts.
I've made my love for Coach's best bags unmistakably clear, but I haven't yet shared how much I adore the New York-based leather goods brand's footwear. Enter: Coach's dark cherry red cowboy boot.
Made of soft, flexible suede, you can scrunch these Free People knee-high boots as much as you like.
Just under $1,000, these Toteme sock boots are the most expensive pair on my wishlist. But given the brand's reputation for simple style and top-notch craftsmanship, I feel confident that this is an investment I will wear for a long time.
Conversely, at just under $100, we have the most affordable boot on my to-buy list: Sam Edelman's on-trend harness bootie in black leather. They're a great alternative for when I prefer not to fuss with styling a knee-high boot but still want to try the moto boho trend.
Magnificently scrunchy boots strutted all over the Fall 2025 runways, and with its wrinkled wedge-heeled knee-high design, Michael Kors's affordable in-house line makes its debut.
Some days, you're not sure if your outfit needs a leather boot or a loafer. Well, you don't have to pick with this hybrid style from Hereu.
