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20 Stylish and Functional Fall Boots to Carry You Through the Season

Ankle, knee-length, riding styles and more.

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Come fall, you're searching for cozy sweaters, warm tights and, most importantly, the perfect pair of boots. Cute fall boots usually aren't hard to come by, but having them also be comfortable can be a challenge. That's why we've rounded up a list of 20 pairs of fall boots that are not only stylish but also super functional. We've got suede and leather options, as well as ankle, knee-high and taller riding styles. Oh, and of course we have some booties on here! Most of the boots on this list are really affordable, but there are few that are on the more expensive side, but we promise, they are worth every penny and will last you years and years to come.

Looking for more fall fashion inspiration? Check out our list of the best fall jackets and fun fall outfit ideas.

1

GLOBALWIN Ankle Boots

Ankle Boots

Pros

    Cons

    Reviewers say these boots are best for travel since they aren't too heavy. They also come in at under $45, which is almost unheard of for fall boots! 

    2

    LifeStride Riding Boot

    On Sale
    Riding Boot

    Perfect for a weekend away or walking the city streets, these riding boots pair well with a long flowy skirt or your favorite leggings and an oversized sweater. Wide sizes are also available. 

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    3
    Wide Calf Style

    DREAM PAIRS Knee-High Riding Boots

    Knee-High Riding Boots

    Finding a good wide calf style boot is nearly impossible, but this pair has over 3,000 5-star reviews on Amazon, with many touting just how great they fit.  

    Cozy looking on the outside and comfy on the inside. The tread will work on slippery days and the treated suede won't get ruined if they get wet.

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    5

    Charles Albert Modern Western Cowboy Distressed Boot

    Best Seller
    Modern Western Cowboy Distressed Boot

    This pair tops our list with over 5,000 5-star reviews on Amazon. Available in a bunch of colors, you can wear them with a fun fall skirt or your favorite pair of skinny jeans. 

    6

    everlane Rain Boots

    Rain Boots
    Now 40% Off
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    These comfy and chic rain boots come with built-in insoles and elastic panels on the side for easy slip on.  FYI: Sizing is based on when worn with thick winter socks, so size up accordingly.  

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    November and December are technically fall, and that means, you might find yourself in a snowy situation. These boots are a best-seller on Amazon thanks to being waterproof, comfortable and stylish. 

    8

    everlane The Glove Boot ReKnit

    The Glove Boot ReKnit

    When testing to find the most comfortable shoes out there, the experts in the Good Housekeeping Institute found these to be the best booties. Reviewers on Everlane's website agree, with one person saying the pair "fits beautifully and are so comfortable."

    RELATED: 22 Most Comfortable Shoes, Sneakers, and Sandals for Women

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    9

    Dr. Scholl's Shoes Double Boot

    On Sale
    Double Boot

    The experts in the Good Housekeeping Institute named these the best wedge heels for cold weather.  They have a memory foam footbed that's contoured to match your foot's shape and they're lightweight and flexible.

    RELATEDThe Most Comfortable Heels to Wear for Work, Weddings and Beyond

    10

    Propet Black Knee-High Boots

    Black Knee-High Boots

    The neoprene placements on these knee-high boots are perfect for the extra stretch you need in the calf area.

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    11

    Columbia Snow Boot

    Snow Boot

    This winter snow boot offers function and style. Its sleek silhouette isn't bulky or heavy, and the technology in this boot offers protection from the elements even in the coldest of weather.

    12

    ZouXou Magda Boot

    Magda Boot

    Handmade in Argentina, the shoes are actually made on demand, meaning your pair was really made just for you. The low heel and memory foam-cushion are just what you need for everyday wear. 

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    13

    Chelsea Paris Tux Loafer Boot

    Tux Loafer Boot

    A true statement boot that will carry you effortessly from fall to winter. The quality is impeccable as is the design. They are also perfect for taking you from day to night. 

    14

    Sugar Foot Bailey Boot

    Bailey Boot

    A classic whiskey color is perfect for the fall season. The boot has an open-toe that allows your feet to breathe, but enough coverage to keep you warm. 

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    15

    Sperry Saltwater Chevron Quilt Nylon Boots

    On Sale
    Saltwater Chevron Quilt Nylon Boots

    Fleece lined, waterproof and totally cute: These quilted boots will keep you happy as you splash around in the elements.

    16

    Nine West Wedge Bootie

    Wedge Bootie

    A wedge heel is easy to walk in all day long. This black classic goes well with anything from your favorite pair of jeans to mini skirts with textured tights. 

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    17

    Sole Rebels XODUS All Over It

    XODUS All Over It

    Hand-crafted in Ethiopia, these boots have a leather body and are lined with wool. "This is the second pair of footwear I've bought from Solerebels. I like that I can wear them in two different ways. And they are so comfortable! It's feels like I'm wearing fluffy house slippers to work," one reviewer wrote. 

    18

    Journee Collection Red Booties

    Red Booties

    Add a little color to your shoe wardrobe with these cherry red ankle booties. The side zip allows for easy on and off.

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    19

    Columbia Newton Ridge Plus Waterproof Hiking Boot

    On Sale
    Newton Ridge Plus Waterproof Hiking Boot

    We do a lot of hiking in the fall, so if you're looking for a good boot for that, this was rated the top pick from our testers and the experts in the Good Housekeeping Institute. The inside features a cushioned midsole and the Omnigrip rubber outsole provides excellent traction. 

    RELATED: 13 Best Hiking Boots for Women, According to Footwear Pros

    20

    MARC FISHER LTD Pointy Toe Booties

    Pointy Toe Booties

    For the minimalist, these boots made of supple leather and a cushioned footbed is the answer to all your sartorial and comfort needs.  

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