Whether you have a capsule fall wardrobe or are still shopping for key pieces, every Prime Woman should have at least one pair of well-made boots. We’ve rounded up our favorite styles of the season, from chic chain details to Western-inspired cowboy silhouettes. Keep reading for the best fall boots to wear this season!
Fall Boots We’re Shopping This Season
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Classic Knee-High Boots (aka Riding Boots)
Fall boot trends for women in 2025 are a blend of timeless styles with fresh, modern updates, offering options for every wardrobe and occasion. One of the standout trends this season is the classic knee-high boot, which continues to dominate the fashion scene. Sleek leather or suede versions in neutral tones like black, brown, and beige are versatile enough to be worn with everything from skirts to tailored trousers. This season, knee-high boots also include added details like square toes or slouchy silhouettes, giving them a contemporary twist.
Pros: This classic boot features a block heel, soft, supple leather, and a chic look. We love that it’ll pair with our favorite dress, boho skirt, or a great pair of jeans.
Pros: Get ready with the Mable boot. This timeless version of the riding boot features sleek leather and a short stacked heel.
Pros: Check out these sleek moto-inspired riding boots with buckled straps at the ankle, a curved antiqued zipper, and an instep zipper for easy pull-on and off.
Pros: The sure-fit shaft with adjustable back corset-inspired lacing lets you customize your calf fit for full comfort. Plus, the full-length side zipper closure allows for easy on/off.
Pros: Crisscrossing straps and rich leather bring distinctive style to this equestrian-inspired boot, which is outfitted with Naturalizer’s signature Contour+ technology, allowing for endless comfort.
Chelsea Boots
Chelsea boots are still a staple, with sleek designs and elastic side panels for easy wear. This season, Chelsea boots are getting an upgrade with lug soles and bold colors, offering a chic but practical option for fall.
Pros: Stretchy side panels and a rear pull tab lend classic elements to a versatile Chelsea boot grounded by a cushioned footbed and stacked block heel.
Pros: Slip into comfort with these Chelsea boots, made of soft leather with elasticized side panels and a loop at the back.
Pros: Keep it simple yet classy by sporting these super-stylish leather boots. With a traditional lace-up closure and pull tabs for added comfort, you’ll love these boots.
Pros: Stylish looks and lightweight comfort in every step make this Chelsea boot a versatile fit for every occasion.
The Best Rain Boots
Rain boots are a practical and stylish choice for fall, offering protection against wet, unpredictable weather. As the season brings rain and muddy conditions, rain boots keep feet dry while adding a fashionable element to any outfit. Popular styles include ankle and knee-high boots, often made from waterproof rubber or PVC. Many come in vibrant colors or patterns, making them a fun accessory that stands out against neutral fall wardrobes. Paired with cozy socks, they can be both functional and comfortable, ensuring you stay dry and chic during fall’s rainy days.
Pros: These boots are made with rubber, which is waterproof and durable. The handmade vulcanized construction prevents weak spots in seams and allows for a fun look and feel.
Pros: These stylish London Fog rain boots will keep you dry no matter how much it rains! Plus, they come in a range of fun and fanciful colors and patterns for every personality.
Pros: These adorable boots are ankle-length, pull-on style, and insulated to keep your tootsies nice and dry on wet, watery days.
Pros: Get through rainy days with ease in these classic rubber rain boots. This style features a buckle accent on the side, logo detailing in front, and a treaded rubber sole for added safety.
Kitten Heel Boots
Kitten heel boots are a stylish, comfortable option for women who want a touch of height without sacrificing ease. Featuring a low heel, typically around 1.5 to 2 inches, these boots offer a chic yet understated look. They’re perfect for both casual and formal outfits, pairing well with dresses, skirts, or tailored pants. Kitten heel boots come in a variety of styles, from sleek leather to textured suede, often with pointed or almond-shaped toes for a refined silhouette. Their modest heel height makes them ideal for all-day wear, blending fashion with practicality for the fall and winter seasons.
Pros: A pointy toe and tapered heel balance a versatile boot shaped in a knee-high silhouette for timeless appeal.
Pros: Antiqued logo hardware makes a signature statement on a knee-high suede boot balanced by a slender square toe and a stacked heel.
Slouchy Boots
Slouchy boots are making a stylish return for fall 2024, offering a relaxed yet sophisticated look. Characterized by their soft, slightly loose fit around the ankle and calf, these boots bring a sense of effortless chic to any outfit. Available in a variety of materials like leather and suede, slouchy boots pair well with everything from skinny jeans to flowy dresses. Neutral beige, brown, and black tones are popular this season, though bolder hues can add a statement. Their laid-back style, combined with comfort, makes them a versatile choice for the cooler months.
Pros: The Sheriff boot features a western-inspired look with a stacked heel and an easy pull-on style. Plus, they go great with dresses, skirts, or cropped pants.
Pros: Retro-inspired and oh-so-versatile, these relaxed, tall leather boots are all you need for transition-season styling.
Pros: These platform wedge boots work great for dressy or casual occasions, and the side zipper allows for easy on/off.
Pros: These chunky block boots are made of faux suede with a jersey lining, allowing for breathable, soft wear in any season.
Pros: This slouched bootie is crafted from supple leather, making it the perfect complement to any cold-weather look.
Western-Inspired Boots
Western-inspired boots, with pointed toes, decorative stitching, and mid-calf heights, are also making a comeback. These boots offer a vintage feel but can be styled in modern ways, such as with oversized blazers or bohemian dresses.
Pros: These western-inspired leather boots are your new go-to boot all season long. They feature a short silhouette, a square pointed toe, and a contrasting sole for added dimension.
Pros: Soft leather crafts a party-ready Western boot with electrifying topstitching against an iconic silhouette.
Pros: These cowboy boots sparkle like stars, swaying with your steps, making you radiate charm on any occasion.
Pros: Soft synthetic lining wicks away moisture to offer a comfortable next-to-skin feel. The cushioning provides ultimate comfort, and a side zipper allows you to easily slip these on and off.
Whether you prefer classic or statement-making styles, fall 2025 offers a wide range of boot trends to explore.
But before you go down a rabbit hole of online shopping for fall fashion, check out our top picks for the best jeans for prime women.
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