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
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 Boothas 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)
Buy the Rockport Cobb Hill Women’s Bethany Boot here.
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)
Buy the Dansko Women’s Maria Boot here.
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)
Buy the FRYE Women’s Addie Double Zip Boot here.
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
Buy the Aerosoles Women’s Bird Cage Boot here.
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
Buy the Lucky Brand Women’s Basel Boot here.
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)
Buy the Cole Haan Women’s Hayes Tall Riding Boot here.
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
Buy the Naturalizer Women’s Tanita Wide-Calf Riding Boot here.
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.
From tall boots and ankle booties to winter worthy snow boots, find lots more ECCO women’s boots right here.