Top 10 Women’s Boots for Fall & Winter

Fall is upon us and winter is coming. Aside from falling leaves and major holidays in quick succession, it’s time to break out the boots! Boots have come a long way from the days where they were reserved for specialized activities such as manual labor or horseback riding, evolving into practical and fashionable options perfect for crisp autumn weather and icy cold winters.  

From knee-highs to ankle booties, there are plenty of trendy styles to choose from. Take a look below for our top 10 picks for women’s boots to carry you through fall and winter in style.  

10. Women’s Cobb Hill Lucinda Lace-Up Boot 

If you’re searching for something that will keep your feet warm as well as turn heads with every step, look no further than our Women’s Cobb Hill Lucinda Lace-Up Boot. Available in classic black and a stunning olive-like green, this irresistible wedge bootie features a deluxe leather upper and provides the best in durability, breathability, and comfort.  

A modest 2.5-inch leawood wedge heel, steel shank, and TR outsole provide the necessary stability and traction to stay upright and balanced when trudging through inclement weather.  

It also features a microfiber lining for added insulation while maintaining a breathable feel, beautifully accented by glossy metal loops and two-toned nubuck panels to create a striking look you’ll want to flaunt until springtime.  

9. Women’s Total Motion Alaiya Ankle Boot 

If you’re aiming for a sleeker look, opt for our Women’s Total Motion Alaiya Ankle Boot, available in black and taupe styles as well as two widths for the best fit possible.  

Our Total Motion technology creates the perfect balance between style and comfort, and the Alaiya Ankle Boot is no exception. The slim, two-inch heel is complemented with foam-backed lining to provide maximum cushioning, while a premium textile lining enhances breathability.  

Perfect for the office and a night out on the town with friends, this ankle bootie exudes poise and confidence with every step.  

8. Women’s Cobb Hill Gratasha 2 Panel Boot  

Simple yet sassy, our Women’s Cobb Hill Gratasha 2 Panel Boot is the perfect boot for hitting the pumpkin patch or the tree farm. Pink, black, and taupe options allow you to make a bold fashion statement or keep things modest, depending on your mood.  

This chic ankle bootie is available in multiple widths for a comfortable fit and features a size zipper for easy on and off. A plush fabric lining offers superior comfort and intricately designed geometric perforations add a bohemian twist.  

7. Women’s Cobb Hill Oliana Bootie  

Turn your style up a notch with our Cobb Hill Oliana Bootie, available in a striking stone brown pull-up leather hue. Low, thick heels allow you to strut your stuff with ease while a classic almond toe provides a softened, tapered look.  

Socks are optional thanks to a flannel lining, so you can quickly step in and take off these boots on busy mornings, and enhanced traction control prevents slippage on rainy autumn days. Easily paired with jeans and leggings, the Cobb Hill Oliana Bootie radiates rustic, timeless style versatile enough for any season.  

6. Women’s Total Motion Oaklee Plain Boot 

If you’re a woman on the go, the Women’s Total Motion Oaklee Plain Boot just might be the shoe for you. This ankle bootie boasts a sensible block heel and comes in floral tapestry and black and brown leather styles.  

The Oaklee Plain Boot is specially crafted with truTECH® and truTECH+® technologies for the best in shock absorption and a durable midsole plate for enhanced support and stability, so you can power you through a long day of fall or winter festivities.  

Adaptable enough for both work and play, this women’s boot is the smart choice for any woman looking to take year-end style to the next level.  

5. Women’s Copley Waterproof Tall Boot 

Our Women’s Copley Waterproof Tall Boot is prepared to take you through the most unpleasant weather while maintaining cool, composed style. Thanks to advanced Hydro-Shield® construction, your feet stay dry and you stay happy as you carry on through a busy, rainy day.  

A microsuede footbed cover improves breathability, while a first-class footbed ensures flexibility and shock absorption for unhindered movement. These boots are also available in a wide calf option.  

4. Women’s Cobb Hill Kailyn Ankle Boot  

Available in grey and black styles, the Women’s Cobb Hill Kailyn Ankle Boot delivers European-influenced style and supreme comfort in one attractive package. Featuring an interior cushion pod, vintage-style buttons, and intricate, laser-cut accents, these ankle boots put your best foot forward, every single time.  

A two-inch block heel and expert construction offer increased stability for balance and confidence with every step. This impressive ankle boot complements a wide range of outfits and exudes worldly, cosmopolitan vibes as soon as you step out the door.  

3. Women’s Total Motion Ariahnna Ankle Boot 

For a slim and sexy look, check out our Women’s Total Motion Ariahnna Ankle Boot offered in taupe, black, and brown shades. Experience chic style while ditching discomfort thanks to our advanced truTECH® and truTECH+® comfort and shock absorption system.  

This 3-inch heeled stunner with a pointed toe and premium suede lining exudes timeless style that can be flaunted not only in fall and winter, but in spring and summer as well. These boots pair well with leggings, short dresses, and cuffed jeans.  

2. Women’s Carly Bootie 

As shown by the boots on this list, the ankle bootie has taken over, and our Women’s Carly Bootie proves that it’s here to stay. This low-heel boot offers high-volume style with edgy side zippers and a perforated panel for a bold, distinctive look.  

Offered in both black and tan shades, this no-nonsense yet fashion-forward shoe boasts a clean leather upper to deliver the absolute best in durability, breathability, and comfort. Perfect for strolls through leaf-scattered parks and chilly late-night adventures, this multipurpose boot can be easily rocked with cutoff jeans or skirts and dresses any time of year.  

1. Women’s Kimly Stretch Bootie  

Looking to add a pop of eye appeal to your fall or winter look? Our Kimly Stretch Bootie in wine or dark taupe microsuede takes any outfit to the next level. If you’re going for a subtler look, this kitten heel classic is also available in black microsuede and black stretch.  

A flexible midsole and premium cushion will have you striding down the sidewalk as if it’s your own personal runway. Advanced Ortholite® footbed technology provides heightened breathability, while a strong rubber outsole offers long-lasting durability so you can continue to rock this chic style season after season.  

Whether you’re a knee-high, mid-calf, or ankle bootie kind of woman, Rockport has what you need to dress to impress all year long. Browse our assortment of women’s boots today and take the first step toward a new season of style.  

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