As soon as the weather turns chilly, I can’t help but get that stir of excitement to slip into my favorite cozy sweaters, jeans and boots. While the warm days of spring and summer are among my favorites, I think most of us find some comfort in those cool autumn mornings that give way to snowy winter days, pumpkin lattes and crackling fires. One of the best ways to embrace the changing seasons is by switching up your clothes and shoes. Tossing aside the sandals and flip flops for fashionable and functional women’s boots is a perfect way to start.
The styles this season are varied and interesting. They’re comfortable and classy, dressy and dressed down. Boots, once relegated to outdoor work, now play a starring role in both professional and casual attire. They’ve become an integral element in nearly every fashion season, but most especially fall and winter. They’re tall, small, and slouchy. From ankle boots and over the knee styles, to dress boots and snow boots, we’ve searched out the best finds for you to consider adding to your collection. Another plus this season is the addition of wide-calf or wide-shaft boots that are more accommodating for women with athletic or larger than average calf sizes. But you’d better hurry, because right now, boots for women are selling fast, and you don’t want to get left with last year’s worn out pair.
While you’re clearing out your closet to accommodate your new boots, don’t forget, now is the perfect time to clean out your dresser too. Update your foundations, from bras to shapewear. Consider buying a warm winter coat now, before it gets really cold. Toss anything you haven’t worn for the past two years, or better yet, donate your unwanted garments to your local women’s shelter or thrift store. Your gently used clothes and shoes can go a long way to making a deserving woman’s day brighter.
Whether you’re looking to amp up your game day outfit, snazz up your business suit, or just keep your tootsies toasty when the snow flies, be sure to check out these Top 20 Best Women’s Boots for Fall & Winter 2018.
Best Women’s Ankle Boots
1. Rockport Cobb Hill Women’s Bethany Boot
1. Rockport Cobb Hill Women’s Bethany Boot
I’ll have to admit, when these cuties landed on my doorstep last week, it was love at first sight. Rockport offered me the opportunity to give these cute fall boots a test run, and I’ve quickly become the envy of my sisters and girlfriends. These women’s boots feature a leather upper and leather lining, and let me just say, that leather is soft as a baby’s behind. From the get go, these fall boots felt like putting on slippers. A really cool design feature, in addition to the snap down loops on the shaft, is the fact that you can slip them on, lace them up for the perfect fit and then never have to do it again. Why? These women’s boots come with a sweet back zipper, so once you cinch them you’re done. The rubber sole is especially grippy, perfect for frosty fall mornings or a skiff of snow. With nine different colors to choose from, you might see me ordering them in grey, red and wine. And I’m not the only one who thinks these ladies boots are terrific, consumers rate them a whopping 4.6 out of five stars. If you’re looking for a more traditional ankle boot to kick around in on a rainy fall day, the Rockport Cobb Hill Women’s Caroline Waterproof Boot is a perfect choice. For a more formal boot that looks great with dressy slacks or jeans, the Rockport Women’s Cobb Hill Kristen Boot has a comfy stacked heel that’s just under three inches, and a side zip for easy on and off.
Price: $89.99 – $169.95 (Up to 44 percent off MSRP)
2. Dansko Women’s Maria Boot
What’s not to love about these adorable grey milled nubuck leather ankle boots from Dansko? They embody this season’s more chunky style, and because they’re Dansko boots, you can count on comfort. This low-cut leather boot features a contoured wooden sole, along with a roomy toe, so you can wear them all day and your feet will still be happy. The side zip entry means they’re easy to toss on with a cute pair of jeans or a mini skirt, and the two inch heel is great for casual comfort. The grippy synthetic sole keeps you safe from slip hazards, and with six color choices (five in milled nubuck and one in full grain leather), you can coordinate with all your favorite fall sweaters and jackets. The Dansko Women’s Michelle Boot delivers a more boho chic style, with a braided leather strap at the ankle, while the Dansko Women’s Dabney Boot features one of this year’s most popular style trends, whip stitching around the top.
Price: $102.99 – $179.95 (Up to 40 percent off MSRP)
3. FRYE Women’s Addie Double Zip Boot
FRYE makes the kind of boots you can wear for a lifetime, so the first time my daughter came home from grad school sporting a pair, I was a little envious. She assured me she’d bought her awesome boots at a thrift store, which made me realize how long lasting they really were. She’s still wearing them 10 years later, and has since purchased a new pair, now that she’s gainfully employed. These gorgeous whiskey colored ankle boots are in full grain, oil tanned Italian leather, but they come in ten colors – both full grain and nubuck leather styles. They feature a leather sole, a comfortable mid-heel, and a rounded toe for easy all day wear. These cool moto-style women’s boots have zippers on both sides to easily slide your foot in and out. I’m guessing you might want to, sooner than later. The FRYE Women’s Naomi Pickstitch Shootie Ankle Bootie is a slightly lower cut boot with spanky wrap-around leather cording and a zipper at the heel. For a tough look on the job or on your Harley, the FRYE Women’s Veronica Belted Short Engineer Boot sports four separate buckle tabs and an inside side zip.
Price: $72.45 – $358.00 (Up to 79 percent off MSRP depending on color and size)
4. Aerosoles Women’s Bird Cage Boot
Tailored-to-perfection, this peep-toe bootie is ready to kick your fall fashion ensemble into action. This style is all about the little details. It features padded trim around the ankle, an angled side zipper and visible stitch lines. Add in a 3½ inch stacked heel, which includes a ½ inch platform, and a lug sole, and you’ve got yourself this season’s full-fashion look. When it comes to comfort, Aerosoles deliver the goods with heel rest technology and a memory foam footbed so you can wear these from dawn to dusk and your feet will feel and look like a million bucks. If you prefer to keep your toes warm and cozy, the Aerosoles Women’s Commentary Boot gives you a chic, mod look with a back zipper and the same comfy heel and footbed. The only missing link between you looking great and the best looking women’s boots is the side chain embellished A2 By Aerosoles Women’s First Role Boot.
Price: $71.83 – $74.98
5. Lucky Brand Women’s Basel Boot
Whether you slip these cute ankle boots on with a great pair of jeans, or you top them with a sleek skirt and sweater, this Lucky Brand boots will make a statement. Low and comfy, they offer a double entry, with double size zips on the inside and out. The unique mesh leather upper gives these low boots an updated look and feel, even though Lucky Brand prides itself on vintage designs. With nearly forty colors and patterns to choose from these women’s boots are a great addition to your shoe wardrobe. Pick one or a number of them to show off your own signature style. For a sassy side buckle look with a simple inner zipper, the Lucky Brand Women’s Bartonn Ankle Bootie looks particularly great with leggings or skinny jeans. Looking for more western styling? The Lucky Brand Women’s Lk-belia Ankle Bootie looks right at home, whether you’re at the rodeo or the football game, with an easy open ankle zip to make slipping in and out of them a breeze.
Price: $37.04 – $245
Best Tall Boots & Riding Boots for Women
6. Clarks Women’s Maymie Stellar Riding Boot
6. Clarks Women’s Maymie Stellar Riding Boot
Luscious cognac leather gives these tall boots an extra special kick. Featuring antiqued studs and wrap around straps, the details of these Maymie Stellar boots form Clarks clue you into why they’re a part of their Artisan Collection. A whip stitched detail at the calf adds to the visual interest of these super classy looking boots. But they’re made to perform, not just look good. They have a super grippy synthetic sole with a robust tread that can get you through the slick stuff. Their cushy heel is approximately two inches, with a half inch platform in front, so they’ll look dressy enough for professional work wear and they’ll be comfy enough for casual weekend wear too. Suede and leather combine for a great look in the Clarks Women’s Mojita Crush Boot. The slightly lower stacked heel gives them a chunkier look that’s great with all of fall’s trendiest styles. The Clarks Women’s Jolissa Lapis Knee-High Boot maintains the riding boot styling with a tumbled leather upper featuring light burnishing at the toe and an ultra-modern buckled ankle strap.
Price: $129.99 – $199.99
7. Sorel Addington Tall Boot
What happens with one of the top snow boot companies steps into the fashion foray to make an all-weather boot? The results are apparent in these awesome Addington tall boots. They’re the perfect mix between sexy and rugged. The full-grain leather upper is waterproof to get you through the worst mother nature has to offer. These women’s boots feature a canvas lining, and the comfortable footbed is made of molded EVA, with a heel cup and arch support, as well as a synthetic topcover. The molded rubber outsole and fashionable leather wrapped heel deliver plenty of traction along with style. If you’re looking for another fashion option in an all-weather boot, Sorel Women’s Cate the Great Wedge Boots feature a mix of leather and suede, along with a lace up closure and grippy rubber soles. The Sorel Women’s Lolla Tall Boot is another waterproof leather boot, with a semi-military style wrap around ankle straps with contrast webbing. Because you’ll likely be wearing thicker socks in fall and winter, and these boots are know to run a tiny bit small, you might want to size up a half size for a perfect fir.
8. Cole Haan Women’s Hayes Tall Riding Boot
Sleek looking and dress, these Cole Haan riding boots feature a nice tall shaft that should hit most women just below the knee. They are extra special because of the beautifully shiny leather that features some sassy buckle detailing at the ankle. Because these are stiffer leather, they won’t bunch up around your ankles and the easy pull, inside zipper means they’re simple to slip in and out of. Sure they’re more on the spendy side, but with good care and waterproofing, you’ll have a great pair of boots that will last for years to come. With a leather sole, you can count on long wear as well. Their timeless styling will continue to look good no matter the fashion trends, and their flatter heel means they’ve got comfort going for them too. If you’re looking for a more casual boot to wear with slacks and jeans, the equestrian-inspired Cole Haan Women’s Kenmare Tall Riding Boots feature pebbled-leather upper with engineer straps at the top line and ankle. If you’ve got more ample calves, the Cole Haan Women’s Dorian Tall Stretch Boot features a leather front with a stretchy fabric back panel, along with the requisite cute straps and buckle detailing.
Price: $160 – $359.97 (Up to 60 percent off MSRP)
9. Best Wide Calf Boots: Naturalizer Women’s Tanita Wide-Calf Riding Boot
If you’re ample in the calves, finding tall boots that fit without feeling uncomfortable can be a real challenge, but these fresh and unpretentious cuties will add tons of style to your wardrobe. The women’s Naturalizer Tanita boot is fabricated from suede leather, with a lightweight but durable construction. This boot has a side zipper for a completely secure fit. It also offers a leather expansion panel in the back to make it extra roomy. It has a fabric and plush faux fur lined interior for enhanced cozy cush and breathability, without adding bulk. Fitted with the N5 comfort system, it offers excellent shock absorption and cushioning support. In addition, it has a synthetic outsole that helps to give you secure heel-to-toe balance for increased flexibility and movement. This cute tall boot gives you form-fitting comfort and long wear. It comes in seven great colors, and I love the navy suede with brown straps, especially with jeans. An elastic gore panel and wide shaft also make the Naturalizer Women’s Jamison Wide-Shaft Riding Boot a great choice that provides a more comfortable fit for athletic and wider calved women. Pebbled leather with front and back buckle details make the Naturalizer Women’s Macnair Wideshaft Riding Boot perfect for a day on your Harley, or horse.
Price: $99.99 – $225
10. ECCO Women’s Sullivan Buckle Riding Boot
Make your fashion debut at work or at play this fall and winter in the smooth and sassy ECCO® Sullivan Buckle Boot. The super shiny leather upper features four adjustable buckles along the side for added appeal. An inside zipper closure makes for easy on and off. These cute tall boots have a breathable textile lining, and a lightly cushioned footbed for comfortable all-day wear. The hidden inner wedge provides a bit of extra heel height, which is always a bonus if you’re not “model tall” and adds to the cushioning comfort. Their durable synthetic outsole has a wavy tread pattern on the front of your foot to give you extra stability on slippery days. The ECCO Women’s Shape 25 Tall Riding Boot features top and ankle buckles and premium calf leather upper that’s soft to the touch.
Price: $99.99 – $287
Best Dress Boots
11. Franco Sarto Women’s L-Ivanea Slouch Boot
11. Franco Sarto Women’s L-Ivanea Slouch Boot
Slouch boots are still the rage, because they’re sexy and dressy at the same time. These flexible slough boots from Franco Sarto give you the best of all worlds with their comfortable platform outsole and their uber-sassy style. These boots can slide up over your knee, or be pushed down for a different look. They’re embellished with a decorative tie around the ankle, and their moderate 3.25 inch heel makes them comforable and classy. The boot shaft measures approximately 20.75 inches from the arch of your foot, giving you lots of flexibility to create your own look. They’ll look great with leggings and a long jacket or under a skirt or dress. If you love nubuck leather, the Franco Sarto Women’s L-Eckhart Boot takes a riding boot design and ups the ante with a three inch stacked heel and long tassle in the back. For a similar look to the L-Ivanea Slouch boot, but for those who might have a larger calf circumference, the Franco Sarto Women’s Ellyn Wide Calf Taupe Boot is a great looking option to flesh out your boot collection.
Price: $49.99 – $115.53
12. Lauren by Ralph Lauren Women’s Sabeen-Bo-Drs Boot
When you’re ready to put on a perfectly polished look, this gorgeous pair of dress boots is an easy way convey your confidence and style. These decidedly luxurious boots reflect both a spirit of heritage and tradition, while evoking sophisticated luxury and style. The gorgeous deep port wine color pairs beautifully with brown, blue, black or grey and gives you a literal leg up on nailing down your own personal style. The leather and suede uppers feature crisscross straps at the ankle and calf. These beauties feature a full-length interior side zip closure, making them easy to slip into or out of. With a moderate 2.5 inch stacked heel, you can bank on comfort and good looks wearing these women’s boots. For an even more formal look, the Lauren by Ralph Lauren Women’s Philena Dress boot features a slightly taller, three inch narrow heel that looks great with skirts and dresses as well as slacks. The Lauren by Ralph Lauren Women’s Geena Riding Boot can swing either dressy or casual, with an almond-shape toe featuring crisscross straps and tassel trims at ankle.
13. Nine West Women’s Sweetkins Dress Boots
These black pebbled leather dress boots strike so many different fashion chords. Their chunkier styling means they can easily go from the boardroom to the bar, with a quick change into casual clothes. The buckle strap above the ankle is an eye-catching embellishment, while the back zipper closure adds to their allure. With a lightly padded footbed, and chunky stacked heel, I’d be pairing these with some wide leg trousers and a sweater or jacket. If you’re looking for an uber-affordable, but good looking dress boot, the Nine West Women’s Kacie Synthetic Boot is under fifty bucks and with a vamp strap and buckle.
Price: $89.99 – $90.99
14. Anne Klein Women’s Yanessi Dress Bootie
This tri-color ankle bootie is as cute as they come, giving you flexibility to wear lots of colors and show off your sassy style. These dressy boots feature a leather toe, flexible fabric sides and a snake skin patterned back, with a slim three inch heel that will lengthen the look of your legs, whether you’re wearing a skirt on slacks. That moderate heel means you’ll be comfortable all day long, while the flexible fabric sides keep your feet from feeling pinched. If you prefer patent leather, the Calvin Klein Women’s Jalana Dress Bootie gives you that same stretchy fabric over the top of your foot and has a sassy side zip entry adorned with the Calvin Klein logo on the zipper pull. The Calvin Klein Women’s Jozie Ankle Bootie is another dressy standout, with brass rivets adorning a higher top upper, but with the same comfy three inch heel. The addition of a buckle strap, and size zip for easy entry make these ankle boots a stylish choice.
Price: $35.99 – $89.00
15. Sam Edelman Women’s Sable Boot
An over-the-knee style in a traditional silhouette, these Sam Edelman Sable dress boots would be an excellent addition to your fall and winter wardrobe. The smooth upper hugs your leg, giving you a sleek profile, while the side-zipper and open back shaft help give you a fitted look. The almond shaped toe looks great when worn under pants or trousers, or, why not show off this boot underneath short skirts and fall dresses? The strappy styling and buckle details give these women’s boots tons of personality, so you can dress them up or down as you wish. Their sweet suede leather would be a perfect complement to cozy sweaters or a boiled wool jacket. For a serious dress-up day at work or an evening out, the Sam Edelman Women’s Asher Ankle Bootie is another suede sweetheart with a sassy peep-toe, that features elasticized crisscross lacing in ghillie-style loops, and a higher heel at 3.75 inches. The Sam Edelman Women’s Arizona Bootie features a fringed top, with an easy entry zide zip and a unique sling back.
Price: $72.31 – $279.95 (Up to 42 percent off MSRP)
Best Women’s Snow Boots
16. Columbia Women’s Ice Maiden II Snow Boot
16. Columbia Women’s Ice Maiden II Snow Boot
Sure-footed, lightweight, and ready for winter’s worst, the women’s Ice Maiden boot lets you storm the snow in style. These snow boots for women will keep your feet nice and toasty, thanks to 200G insulation. These snow boots are waterproof, while giving you a feminine look. Their grippy rubber sole ensures you can face winter weather with confidence, and they have great foot cushioning, to keep your feet firmly in place, without sliding around inside. The wide front ties let you cinch them tight to keep out the cold, snow and rain. Another highly rated option is the Columbia Women’s Minx Mid II Omni-Heat Winter Boot. It’s waterproof, woven synthetic upper features jacket-like baffling. Faux-fur at at the collar and tongue make a fashion statement, while 200G insulation, a heat-trapping reflective lining, and advanced traction outsole mean you can face the fiercest winter storm. If you happen to live in a cold, but drier climate where you rarely get deep snow, the Columbia Women’s Sierra Summette Shorty Winter Boot is a super cute and cozy option.
Price: $46.47 – $95.00 (Up to 48 percent off MSRP)
17. Sorel Women’s Joan Of Arctic Boot
I bought my first pair of Sorel boots 20 years ago, and just finally replaced them last year. These women’s snow boots will let you conquer the cold weather season in warm, totally waterproof comfort. They feature a toasty faux fur snow collar and lace up front with rugged D-ring laces. One of my fave things about these awesome snow boots is the removable felt liner. Sure, you’re asking right now “if they’re waterproof, why would I need a removable liner?” aren’t you. Think about it, your feet sweat, especially when they are warm and it’s cold outside. It’s great to have a liner that you can take out to air out and dry, plus it can be a bit easier slip into before getting into your outer boot. It’s the one feature I think makes these boots a cold weather standout. The rugged rubber sole grips on both snow and ice to keep you on your feet when winter weather strikes. If you’re more serious about outdoor work in the winter, consider the Sorel Women’s Caribou Boot. While you might not feel quite as much of a fashionista in these boots, I own them and love them for the toughest days of shoveling snow and snow shoeing too. Soft nubuck pairs with a rugged waterproof rubber shell on these timeless, utilitarian boots, and the removable felt ThermoPlus lining is trimmed with plush sherpa which isn’t quite as cute as faux fur, but sure feels great when it’s cold out.
Price: $89.00 – $249.95 (Depending on size and color selected)
18. Kamik Women’s Snowvalley Boot
Whether you’re trekking through the mountains or the snow-packed city streets, the mid-calf Snowvalley warm women’s snow boot has you covered. These winter boots have a classic styled, quilted nylon upper with suede overlays to keep you looking stylish, paired with 3Mtm Thinsulate insulation to keep the warmth in, without weighing you down. Featuring seam-sealed waterproof construction, you can count on your tootsies being warm and protected with every step. The gusseted tongue means these are easy to loosen or tighten depending on your socks, so you can go from wool to the thickest fleece with no worries. Get them in any one of fifteen color combinations to suit your personal style. The Kamik Women’s Pinot Snow Boot features a trendy wedge sole, and a Dri Defense 100% waterproof membrane lining that keeps feet warm and dry with a less bulky boot. The Kamik Women’s Harper Snow Boot gives you the flexibility to wear a high or low boot with its convenient foldover collar that reveals a faux fur interior that’s as soft as your favorite teddy bear.
Price: $45.00 – $120.00
19. Khombu Women’s Cooper Snow Boot
The cute and sassy Cooper snow boot is carefully crafted with waterproof suede, and it’s just the ticket for not too serious winter fun. If you’re just kicking around town, or braving the weather to walk between appointments, the Cooper offers you a quick inside zip closure for easy on and off. But what makes it so stylish is the faux fur topper and the clever loop and button detail with double tasseled ends. These ankle boots feature thermolite insulation, and the k grip outsole promises you all day comfort, along with great traction. If you’re looking for a mid-calf boot with a classy touch of patent leather, the Khombu Women’s Ally Snow Boot is a stylish and affordable choice that’s warm, waterproof and slip resistant. The Khombu Spice Women’s Winter Boot features a comfy rounded toe box, along with a cozy faux fur collar and an oh-so-clever double buckle strap side detail, along with an easy entry zipper.
Price: $29.99 – $75.00
20. Best Buy: Skechers Women’s Grand Jams Unlimited Boot
These smoking hot SKECHERS® snow boots meet you right in the middle of fashion and function. These cute cold weather boots feature a suede upper with plush faux-fur trim. The half-zip closure and lace-up front means once you cinch them to the perfect fit you won’t have to do it every time you slip them on. The fold-over cuff can be worn up or down, meaning they’ll look adorable with warm leggings or a skirt. For extra comfort, they have a lightly cushioned man-made footbed. For the best winter durability, be sure to pre-treat the suede with waterproofer before you wear them in the rain or snow. A sweater knit foldover top and cute buckle detail make the Skechers Women’s J’adore Ankle Boot a great cool weather choice for casual football games or just a walk around the neighborhood. For an easy pull on women’s snow boot, the Skechers Women’s Keepsakes-Brrrr Boot features a rich suede upper with ruched shaft and three wooden button detail.
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