I am a shoe gal through and through. I invest in my shoes and always want pairs I’ll wear again and again. With the return of boot season, I’m sharing the best fall boots for women, from everyday ankle boots and classic riding boots to knee-high styles, waterproof boots and dressier pairs.

Many of these are boots I’ve personally owned and worn for years, so I’m also sharing notes on comfort, fit and how I actually style them. Whether you’re looking to invest in a new pair for fall or want ideas for styling boots you already own, these are the styles I recommend most.

Read on for my favorite fall boots for women, freshly updated for Fall 2026.

The Best Fall Boots For Women

In this post I’ll cover:

• Best ankle boots
• Best kitten heel boots
• Best Chelsea boots
• Best suede boots
• Best lug sole boots
• Best riding boots
• Best knee-high boots
• Best dress boots
• Best rain boots
• Best western boots

The below pairs I have found to all be TTS for me and I take my usual size 7.

Ankle Boots

These booties were the best pair of shoes I bought in 2017 and remain a favorite many years later. I can go for miles and miles without any issues with these little booties and I love styling them with both jeans as seen here or with dresses.

I get compliments on them whenever I wear them and truly find myself reaching for them in Fall + Winter at least twice a week. They also come in a gorgeous cognac color I added to my collection a few years back.

Block Heel Ankle Boots

The Staud Wally boots I got a few years ago and I get a lot of wear out of them thanks to them being so comfortable.

They have a variety of styles and colors of the silhouette for this year and even a knee high version I am eyeing.

Look for less here.

Kitten Heel Boots

I’d always heard good things about this brand and eyed a lot of their styles so finally invested in this on-trend, yet classic pair of oh so comfortable and walkable boots. The leather is gorgeous. 

If you prefer a block heel, try these.

A similar look for less from Marc Fisher HERE.

Chelsea Boots

Chelsea boots are great because they often allow for loads of miles but are stylish to go with most of your Fall & Winter outfits. Better yet? They hold up in rain and light snow, too if you buy a quality pair.

Pointed Toe Suede Boot

If you prefer a pointed toe, the Margaux Downtown Boot may also be perfect for you.

Margaux’s Downtown Boot features a stacked heel and a low shaft. The Chocolate Brown color is so beautiful but they have additional colors, too.

I’ve worn these so, so much in Europe to log a lot of miles on Fall and Winter trips.

Or consider the J.Crew Pull On Boots.

Lug Sole Boots

I get so much wear out of are the Freda Salvador Brooke Boot that are chic yet so practical because the suede and leather is water resistant. Practical and yet so stylish. I travel with these often because they are shockingly lightweight.

I love them so much I own the black leather and espresso suede as well. You can use code WITWHIMSY10 for 10% off your first order from Freda Salvador.

These Sam Edelman lug boots are similar and less expensive. This chocolate suede color they come in is also beautiful.

Riding Boots

I looked for what felt like years to find the perfect riding boot. I wanted something unbranded (read: no logos!), something that felt really timeless, was comfortable and was slim. When I saw these Khaite Riding Boots I loved them but not at their price point. But years ago by some stroke of luck and a tip from a friend, they were briefly marked down on Saks during one of their sales and I scored them for over 40% off. 

I took my usual size 37 in these and I did have to bring them to my cobbler to have the shafts stretched as I found them rather narrow.

A good look for less I recently spotted is this pair and this pair.

Stylish Sock Booties

These Inez booties are so comfortable that they are a go-to shoe for me when I go to Europe. I’ve been wearing them since 2019! I first bought the beautiful neural Ginger suede and then the black calf.

You can use code MEGHAN15 for 15% off your purchase of Inez shoes.

Leather Knee-High Heeled Boot

A timeless style to pair with skirts and dresses, the Loeffler Randall Goldy Boots are so stylish and so beautifully made. I’ve relied on these boots for many years and always found them really comfortable.

They are also available in a gorgeous cognac color. And finally a wide calf version, too!

If you prefer a lower heel try this pair.

Suede Knee-High Boots

And for dressier looks, I reach for these gorgeous Larroude boots. They are so comfortable and chic.

Lastly, I also love the soft brown color of this pair by Inez.

Dress Boots

The Sarah Flint Dress Bootie is the quintessential bootie for dressier occasions all Fall and Winter. Designed with extra foot padding these are comfortable and just so beautifully made. They also have a lower heel version if you’d prefer that.

I love the look of this pair from Inez, too.

Rain Boots

I have both the High Gloss classic Hunter Rain Boots and the packable boots that are perfect for travel where you’ll inevitably run into rainy Fall days.

Western Boot

Pointed toes and embroidered details make a nice change and embrace an on-trend style. I’m not one to wear cowboy boots so I lean into this style in a minimal boot like the above Staud Western Wally.

I saw Western-inspired boots like this pair everywhere in Milan earlier this month and expect them to be one of the bigger boot trends for Fall 2026.

. . .

How to Choose the Best Fall Boots

When it comes to buying boots for fall, I always think about cost per wear. I would much rather invest in one beautifully made pair that I’ll reach for year after year than buy several trendier pairs that don’t hold up or aren’t comfortable enough to actually wear. I live in New York and walk everywhere, so comfort is just as important to me as style.

Consider How Much Walking You’ll Do

Comfort is always one of my biggest considerations when buying boots. If you’ll be walking a lot, look for a supportive sole, a manageable heel and enough room in the toe box. I also pay attention to the weight of a boot. Some lug sole and riding boots can feel surprisingly heavy after a few hours of wear.

Think About Your Fall Weather

Leather is generally my preference for an everyday fall boot because it is durable and can handle unpredictable weather, particularly when properly cared for. I love suede, too, but tend to be more mindful about the forecast when wearing it. If you live somewhere that gets a lot of rain or early snow, I think having at least one waterproof or weather-resistant pair in your wardrobe is well worth it.

Choose a Shaft Height You’ll Actually Wear

Think about the pants, jeans, skirts and dresses you wear most often before choosing a boot. Ankle boots are incredibly versatile with denim and trousers, while I love knee-high boots with skirts and dresses. A slim riding boot is another timeless option that works beautifully with both dresses and more casual looks.

Consider Your Existing Wardrobe

Before buying a new pair, I always ask myself how many outfits I can envision wearing them with. Black and rich brown leather are among the most versatile options in my wardrobe, while suede can add beautiful texture to an otherwise simple fall outfit. The best boots aren’t necessarily the most exciting pair in the store — they’re the ones you’ll find yourself reaching for again and again.

Invest Where It Makes Sense

Boots are one of the categories where I personally think it can be worth spending more for quality. I put my shoes through their paces living in New York and traveling, and many of the boots featured in this post have been in my wardrobe for years. I take good care of them, have them repaired by a cobbler when needed and would much rather own fewer pairs that I genuinely love wearing.

Fall Boots FAQs

What boots are in style for Fall 2026?

For Fall 2026, I’m seeing plenty of timeless boot silhouettes that make getting dressed easy: sleek knee-high boots, riding boots, pointed-toe ankle boots, kitten heels, rich suede and western-inspired styles. Chocolate brown continues to be particularly beautiful for fall and is an easy alternative to classic black.

I don’t recommend buying boots based solely on trends, though. I tend to look for classic silhouettes with subtle modern details so they’ll still feel relevant several seasons from now.

Are ankle boots still in style in 2026?

Yes. Ankle boots remain a fall wardrobe staple, although the specific silhouettes continue to evolve. I prefer streamlined styles with an elongated or pointed toe, a kitten or block heel or a classic Chelsea boot silhouette. They work particularly well with jeans and trousers and are easy to dress up or down.

And personally, I don’t like a gap between where my pants end and my boots begin — or socks showing in between!

What Socks to Wear with What Shoes

Are riding boots still in style?

Riding boots are a classic style that I have worn for years. I particularly love a streamlined riding boot without prominent logos or hardware because it feels timeless and is easy to style. I find them quite situational. I’ll wear mine in the English Countryside for example.

You can wear them with dresses and skirts or over slim pants and leggings for a more casual look.

What boots look best with straight-leg jeans?

Ankle boots are my go-to with straight-leg jeans. 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 beautifully depending on how dressed up you want the outfit to feel.

What boots should you wear with dresses in the fall?

I love knee-high boots with fall dresses. A slim riding boot makes a dress feel more casual while a heeled leather or suede boot can immediately dress it up. Ankle boots can work well, too, particularly with midi and maxi dresses.

What color boots are the most versatile?

Black is hard to beat for versatility, particularly if much of your wardrobe is neutral. I also get a lot of wear out of rich brown and cognac boots. Brown suede is especially beautiful in the fall and pairs well with denim, cream, camel, navy, burgundy and other seasonal shades.

Are suede boots practical for fall?

They can be, but I am more careful about when I wear suede than leather. I avoid wearing my favorite suede boots when significant rain is in the forecast and protect them before their first wear. No matter what, before I ever wear a pair of suede shoes, I always spray them with this protectant spray.

For truly wet fall days, I reach for leather, waterproof boots or rain boots instead.

What are the best boots for walking?

For days when you’ll be doing a lot of walking, prioritize comfort over heel height. I look for 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 some of the styles I reach for most when I know I’ll be putting in serious mileage.

This pair really fits the bill for me for days when I know I’ll be walking a lot.

Most of these pairs of boots I’ve had for years. I take excellent care of my shoes but I also walk in them a lot living in New York. It’s why I invest in pairs and in brands that I know put quality first. So while the above may seem pricey, they have served me well and for much longer than when I buy less expensive boots.

Shop the Best Fall Boots for Women

 

You May Also Like:

• Things in My Closet I am Wearing this Fall.
• What Shoes to Pack for Europe.
• Sezane’s Best New Fall Arrivals.

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