Women's Heeled Boots

Women's heeled boots are a timeless addition to any wardrobe, offering a blend of classic style and everyday versatility. Whether you're heading out for a casual afternoon or dressing up for an evening gathering, these boots provide just the right amount of lift and comfort. With quality construction and durable materials, women's heeled boots from L.L.Bean are designed to keep up with your busy days while adding a touch of effortless style to every step.

Sort by:

Filter & Sort

476 Items

Women's Blundstone Heeled Chelsea Boots

A versatile black leather boot with a 2" heel, cushioned midsole, and durable thermoplastic outsole.
Women's TOMS® Everly Chelsea Boots, Suede
Price was from: $119.95 now: $99.99

An oatmeal suede leather ankle bootie with dual gore panels and a 2 3/4" stacked heel.
Women's Stonington Chelsea Boots, Leather
Price was from: $150 now: $119.99

A rugged dark oakwood leather chelsea boot with sneaker-like comfort and durable rubber outsole.
Women's TOMS® Everly Chelsea Boots, Nubuck
Price was from: $119.95 now: $99.99

A stylish black nubuck leather ankle bootie with a 2 3/4" stacked heel and cushioned OrthoLite® insole.
Women's Stonington Chelsea Boots, Suede
Price was from: $150 now: $119.99

A pair of graphite suede Chelsea boots with sneaker-like comfort, moisture-wicking lining, and durable rubber outsole.
Women's Camden Hills Chelsea Boots
Price was from: $190 now: $94.99

A stylish Chelsea boot with full-grain leather, cushioned EVA footbed, and rugged rubber outsole for all-day comfort.
Women's Camden Hills Alpine Boots

A rugged and stylish black alpine boot with full-grain leather, wool lining, and VertiGrip rubber outsole.
Women's NextVenture Boots, Chelsea
Price was from: $150 now: $111.99

A tan Chelsea boot with waterproof nubuck uppers, cushioned EVA midsole, and Vibram rubber outsole for traction.

Women's Heeled Boots

Heeled boots for women have a way of adding a little lift to every step, both literally and figuratively. Whether you're heading out for weekend errands, catching up with friends over coffee, or simply enjoying a crisp winter walk, the right pair of heeled boots can make all the difference. The best styles are thoughtfully designed to offer comfort and support, so you can move with confidence from morning to night. Look for pairs with cushioned footbeds, sturdy block heels, and outsoles that provide reliable traction—especially important during the colder months when sidewalks can be slick with snow or slush. Many women appreciate the versatility of heeled boots, as they're easy to dress up or down. Pull them on with your favorite jeans and a cozy sweater for a laid-back afternoon, or pair them with a skirt and tights for a polished look that still feels relaxed and practical. If you're shopping for someone else, heeled boots make a thoughtful gift for anyone who loves to blend timeless style with everyday function—think daughters heading back to campus, friends who enjoy winter strolls, or sisters who appreciate a little extra height without sacrificing comfort.

When considering which heeled boots to add to your collection, think about the features that matter most for your lifestyle. Durability is key, especially if you plan to wear them often or through unpredictable weather. Look for high-quality materials that can handle daily wear and resist the elements, so your boots stay looking great season after season. Easy on-and-off designs, like side zippers or pull-on tabs, are a welcome touch when you're heading out the door in a hurry. And with winter in full swing, it's worth exploring options with cozy linings or weather-ready details that help keep your feet warm and comfortable, even on the coldest days. If you're looking for boots that combine the classic appeal of a heel with winter-ready features, take a look at our selection of Women's Winter Heeled Boots—they're crafted to keep up with whatever the season brings, from snowy sidewalks to festive get-togethers.

Heeled boots are also a great way to express your personal style while staying practical. With so many silhouettes, colors, and heel heights to choose from, it's easy to find a pair that feels just right for your wardrobe and your routine. Some women reach for sleek, understated designs that transition seamlessly from workdays to weekends, while others prefer boots with a bit of rugged charm for outdoor adventures or casual outings. No matter your preference, a well-made pair of heeled boots is a reliable companion through all kinds of winter weather and beyond. They offer lasting value, timeless style, and the kind of comfort that lets you focus on making the most of every day—whether you're out exploring new places or simply enjoying a quiet moment by the fire.

It's time to upgrade your browser

Women's Heeled Boots