Every September my closet does the same thing: half of it is still summer, and the other half is asking to come out for the last two months it’s allowed to. Boots are where I do my best fall spending β and my most regrettable ones. So when I update this list, I’m not shopping the season. I’m auditing what survived.
Here are the best fall boots for women, from the ankle booties I’ve had since 2017 to the riding boots I hunted for years. Every pair on this list is one I’ve owned, worn for real miles, and still reach for. Freshly updated for Fall 2026.
One note before the list: the pairs below run true to size for me β I’m a size 7 β so if a brand typically runs small or large for you, size up or down accordingly.
The best fall boots, by category
Ankle boots: the workhorse
The first ankle booties I bought in 2017 are still the best pair of shoes I own. I can walk miles in them without a single complaint, they’ve earned compliments every single time, and I reach for them at least twice a week through fall and winter. They come in a gorgeous cognac color I added a few years back, and they’re the reason I never shop for a replacement β the original never stopped working.
Block heel and kitten heel ankle boots
The Staud Wally is my go-to block heel boot β I got it a few years ago and the comfort is the whole story. The brand keeps doing the silhouette in new colors, and there’s a knee-high version I’ve been eyeing. If you want a similar shape at a lower price point, there are plenty of look-alikes worth checking before you pay designer money.
For a kitten heel, I finally invested in a pair I’d been admiring from afar for years: on-trend but classic, gorgeous leather, and genuinely walkable. That combination is rarer than it should be. If a block heel suits you better than a kitten, there are close alternatives in the same family.
Chelsea boots: the ones that hold up
Chelsea boots do a lot of miles and still look good doing it β they’re the easiest boot to pull off with most of your fall and winter outfits. Buy a quality pair and they’ll hold up through rain and light snow too, which matters if you walk anywhere.
If you prefer a pointed toe, the Margaux Downtown Boot is a strong option: stacked heel, low shaft, and a chocolate brown that’s genuinely beautiful. I’ve worn them extensively on fall and winter trips in Europe, and they’ve logged serious miles. J.Crew’s pull-on boots are a solid alternative in the same spirit.
Lug sole boots: practical that happens to be chic
The Freda Salvador Brooke Boot gets more wear than almost anything in my closet. The suede and leather are water-resistant, they’re shockingly lightweight, and they’re the pair I travel with. I own the black leather and espresso suede versions. If you want a similar lug boot for less, Sam Edelman makes a comparable style β their chocolate suede color is beautiful, too.
Riding boots: the search was worth it
I looked for what felt like years for the perfect riding boot: unbranded, timeless, slim, comfortable. When I found the Khaite Riding Boots, I loved them β but not at full price. Then a friend tipped me off that they were briefly marked down at Saks during a sale, and I scored them for over 40% off. I took my usual size 37 and had a cobbler stretch the shafts, which were a touch narrow. A cobbler visit is a small price for the pair I now reach for most.
There are look-for-less options in the same silhouette if you want to skip the investment tier entirely.
Sock boots: the travel pair
The Inez sock bootie is so comfortable it’s become my default for Europe. I’ve worn them since 2019 β first in the beautiful neutral ginger suede, then in black calf leather. That’s two seasons’ worth of airport miles in one shoe, and they still look good.
Knee-high boots: for dresses and skirts
The Loeffler Randall Goldy Boot is a timeless style I’ve relied on for years: beautifully made, genuinely comfortable, and made for skirts and dresses. They come in a gorgeous cognac, and there’s now a wide-calf version if that’s your fit. If you’d rather have a lower heel, there are excellent options one notch down.
For dressier looks, I reach for the Larroude suede knee-highs β chic, soft, and comfortable enough to actually wear. The soft brown Inez knee-high is another pair I love for the same reason.
Dress boots
The Sarah Flint Dress Bootie is the one for dressier fall and winter occasions: extra foot padding, beautiful construction, and a lower heel version if that’s your preference. It’s the pair that turns a simple black dress into an occasion.
Rain boots
I own the classic Hunter High Gloss rain boots and the packable version, which lives in my travel bag because fall in a new city almost always means at least one rainy day. One waterproof pair in the closet is not a luxury β it’s the pair that saves a good outfit.
Western boots
Pointed toes and embroidered details make a welcome change, and I’m not a cowboy-boot person, so I lean into the style in a minimal silhouette like the Staud Western Wally. I saw western-inspired boots everywhere in Milan earlier this month, and I expect them to be one of the bigger boot trends for Fall 2026. My advice: try on the minimal version first β it’s the one that will outlive the moment.
How I choose my fall boots
Start with cost per wear, not the price tag
I’d rather invest in one beautifully made pair I reach for year after year than three trendier pairs that don’t hold up. I live in New York and walk everywhere, so comfort is just as important as style. A boot that costs more but gets worn again and again has already paid for itself.
Consider how much walking you’ll do
If you walk a lot, look for a supportive sole, a manageable heel and room in the toe box β and pay attention to weight. Some lug sole and riding boots feel surprisingly heavy after a few hours. That heaviness is what kills a boot before the heel does.
Think about your actual weather
Leather is my everyday preference because it’s durable and handles unpredictable weather, particularly with care. I love suede too, but I check the forecast before wearing it. If your city gets early rain or snow, at least one waterproof or weather-resistant pair is well worth it.
Choose a shaft height you’ll actually wear
Look at the jeans, trousers, skirts and dresses you already own. Ankle boots are incredibly versatile with denim and trousers; knee-highs shine with skirts and dresses; a slim riding boot works beautifully with both. If a height only works with clothes you don’t own, it’s not a boot β it’s a wish.
Check it against your existing wardrobe
Before I buy, I ask how many outfits I can envision with the pair. Black and rich brown leather are the most versatile options in my closet, while suede adds texture to an otherwise simple fall outfit. The best boots aren’t the most exciting pair in the store β they’re the ones you’ll find yourself reaching for again and again.
Invest where it makes sense
Boots are one of the few categories where I think it’s worth spending more for quality. Many of the boots in this post have been in my wardrobe for years. I take care of them, have them repaired by a cobbler when needed, and would rather own fewer pairs I genuinely love.
Fall boots, answered
What boots are in style for Fall 2026?
Timeless silhouettes that make getting dressed easy: sleek knee-highs, riding boots, pointed-toe ankle boots, kitten heels, rich suede, and western-inspired styles. Chocolate brown is particularly beautiful this year and an easy alternative to black. I don’t buy boots on trends alone β classic silhouettes with subtle modern details are the ones that still feel relevant in a few seasons.
Are ankle boots still in style?
Yes. Ankle boots remain a fall staple, though the specific silhouettes keep evolving. I prefer streamlined styles with an elongated or pointed toe, a kitten or block heel, or a classic Chelsea shape. They work with jeans and trousers and are easy to dress up or down. One personal note: I don’t like a gap between where my pants end and the boot begins β or socks showing in between.
Are riding boots still in style?
They’re a classic I’ve worn for years. I love a streamlined riding boot without prominent logos or hardware β it feels timeless and is easy to style. I’ll wear them with dresses and skirts, or over slim pants for something more casual. They’re quite situational for me; my pair gets its most wear in the English countryside.
What boots look best with straight-leg jeans?
Ankle boots. Look for a shaft that sits neatly beneath the hem of the denim rather than creating bulk around the ankle. Pointed-toe, kitten heel and Chelsea boots can all work, depending on how dressed up you want the outfit to feel.
What boots should you wear with dresses in the fall?
Knee-highs are my first reach. A slim riding boot makes a dress feel more casual; a heeled leather or suede boot dresses it up immediately. Ankle boots work too, particularly with midi and maxi dresses.
What color boots are the most versatile?
Black, particularly if much of your wardrobe is neutral. I also get a lot of wear out of rich brown and cognac. Brown suede is especially beautiful in the fall and pairs well with denim, cream, camel, navy and burgundy.
Are suede boots practical for fall?
They can be, but I’m more careful with suede than leather. I avoid my favorite suede pairs when significant rain is in the forecast, and I spray them with a protectant before their first wear. For truly wet days, I reach for leather, waterproof or rain boots instead.
What are the best boots for walking?
Prioritize comfort over heel height: cushioning, a supportive sole, a comfortable toe box, and a boot that isn’t overly heavy. Chelsea boots, lightweight lug sole boots and lower-heeled ankle boots are the styles I reach for on serious-mileage days.
The Edit
If you buy one pair this season: a quality Chelsea boot in black or chocolate brown. It covers the most outfits, survives the most weather, and will still be working for you in a few years. That’s the whole philosophy in one shoe.
A note from Margot
I spent ten years editing magazine racks. Now I edit your closet β and I promise you already own half of what fall needs. The boots that last are never the loudest ones in the store.
