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Comfortable Heeled Boots

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Women's Heeled Chelsea Booties

Women's Heeled Chelsea Booties

Blundstone Women's Heeled Chelsea Booties

Evelyn Leather Heeled Booties

Evelyn Leather Heeled Booties

TOMS Evelyn Leather Heeled Booties

Internet Exclusive

Graceful Suede Tall Boots

Graceful Suede Tall Boots

Copper Key Graceful Suede Tall Boots

Dillard´s Exclusive

Hunny Microsuede Block Heel Tall Boots

Hunny Microsuede Block Heel Tall Boots

Steve Madden Hunny Microsuede Block Heel Tall Boots

Hunny Block Heel Tall Boots

Hunny Block Heel Tall Boots

Steve Madden Hunny Block Heel Tall Boots

Elevate Suede Kitten Heel Tall Boots

Elevate Suede Kitten Heel Tall Boots

Matisse Elevate Suede Kitten Heel Tall Boots

Toni Leather Block Heel Booties

Toni Leather Block Heel Booties

Born Toni Leather Block Heel Booties

Permanently Reduced

Harriet Slouch Nubuck Mid Calf Block Heel Boots

Harriet Slouch Nubuck Mid Calf Block Heel Boots

Schutz Harriet Slouch Nubuck Mid Calf Block Heel Boots

Evelyn Metallic Suede Heeled Booties

Evelyn Metallic Suede Heeled Booties

TOMS Evelyn Metallic Suede Heeled Booties

Martha Leather Block Heel Chelsea Booties

Martha Leather Block Heel Chelsea Booties

Sofft Martha Leather Block Heel Chelsea Booties

Anneliese Leather Chelsea Block Heel Booties

Anneliese Leather Chelsea Block Heel Booties

ALDO Anneliese Leather Chelsea Block Heel Booties

Internet Exclusive

Gylina Suede Tall Block Heel Boots

Gylina Suede Tall Block Heel Boots

Vince Camuto Gylina Suede Tall Block Heel Boots

Permanently Reduced

Abrams Suede Tall Western Kitten Heel Boots

Abrams Suede Tall Western Kitten Heel Boots

Matisse Abrams Suede Tall Western Kitten Heel Boots

Basel Smooth Leather Side Zip Block Heel Booties

Lucky Brand Basel Smooth Leather Side Zip Block Heel Booties

Celeste Suede Pointed Toe Block Heel Mid Calf Boots

Celeste Suede Pointed Toe Block Heel Mid Calf Boots

Matisse Celeste Suede Pointed Toe Block Heel Mid Calf Boots

Sonya Leopard Suede Waterproof Kitten Heel Boots

Sonya Leopard Suede Waterproof Kitten Heel Boots

Sofft Sonya Leopard Suede Waterproof Kitten Heel Boots

Travers Leather Block Heel Tall Boots

Travers Leather Block Heel Tall Boots

Gianni Bini Travers Leather Block Heel Tall Boots

Dillard´s Exclusive

Dantelle Suede Block Heel Tall Boots

Dantelle Suede Block Heel Tall Boots

Steve Madden Dantelle Suede Block Heel Tall Boots

Pepper Leather Kitten Heel Tall Dress Boots

Pepper Leather Kitten Heel Tall Dress Boots

Naturalizer Pepper Leather Kitten Heel Tall Dress Boots

Holy-Grail Leather Block Heel Booties

Holy-Grail Leather Block Heel Booties

GB Holy-Grail Leather Block Heel Booties

Dillard´s Exclusive

McKay Suede Kitten Heel Booties

McKay Suede Kitten Heel Booties

Lauren Ralph Lauren McKay Suede Kitten Heel Booties

Francesca Suede Kitten Heel Ankle Booties

Francesca Suede Kitten Heel Ankle Booties

Bruno Magli Francesca Suede Kitten Heel Ankle Booties

Internet Exclusive

Helm Suede Ankle Booties

Helm Suede Ankle Booties

Naot Helm Suede Ankle Booties

Internet Exclusive

Timmy Suede Kitten Heel Tall Boots

Timmy Suede Kitten Heel Tall Boots

Franco Sarto Timmy Suede Kitten Heel Tall Boots

Permanently Reduced

Valora Leather Block Heel Tall Boots

Valora Leather Block Heel Tall Boots

Vionic Valora Leather Block Heel Tall Boots

Wili Leather Western Block Heel Booties

Wili Leather Western Block Heel Booties

Donald Pliner Wili Leather Western Block Heel Booties

McKay Suede Kitten Heel Tall Boots

McKay Suede Kitten Heel Tall Boots

Lauren Ralph Lauren McKay Suede Kitten Heel Tall Boots

Daney Leather Block Heel Ankle Booties

Daney Leather Block Heel Ankle Booties

Steve Madden Daney Leather Block Heel Ankle Booties

Tyrell Suede Block Heel Tall Dress Boots

Tyrell Suede Block Heel Tall Dress Boots

Gianni Bini Tyrell Suede Block Heel Tall Dress Boots

Dillard´s Exclusive

Women's Block Heeled Water-Resistant Leather Booties

Women's Block Heeled Water-Resistant Leather Booties

Blundstone Women's Block Heeled Water-Resistant Leather Booties

Luella Suede Block Heel Booties

Luella Suede Block Heel Booties

Franco Sarto Luella Suede Block Heel Booties

Internet Exclusive

Brent Weatherproof Leather Block Heel Tall Boots

Brent Weatherproof Leather Block Heel Tall Boots

Naturalizer Brent Weatherproof Leather Block Heel Tall Boots

Women's Miana Leather Heeled Waterproof Chelsea Boots

Women's Miana Leather Heeled Waterproof Chelsea Boots

Hunter Women's Miana Leather Heeled Waterproof Chelsea Boots

Riggs Leather Block Heel Tall Boots

Riggs Leather Block Heel Tall Boots

Steve Madden Riggs Leather Block Heel Tall Boots

Daney Suede Block Heel Ankle Booties

Daney Suede Block Heel Ankle Booties

Steve Madden Daney Suede Block Heel Ankle Booties

Sharnell Heel Suede Adjustable Waterproof Western Inspired Boots

Sharnell Heel Suede Adjustable Waterproof Western Inspired Boots

Sofft Sharnell Heel Suede Adjustable Waterproof Western Inspired Boots

Permanently Reduced

Women's Miana Suede Heeled Waterproof Chelsea Boots

Women's Miana Suede Heeled Waterproof Chelsea Boots

Hunter Women's Miana Suede Heeled Waterproof Chelsea Boots

Celeste Leather Pointed Toe Block Heel Mid Calf Boots

Celeste Leather Pointed Toe Block Heel Mid Calf Boots

Matisse Celeste Leather Pointed Toe Block Heel Mid Calf Boots

Internet Exclusive

Sashan Suede Tall Boots

Sashan Suede Tall Boots

Guess Sashan Suede Tall Boots

Idris Suede Tall Boots

Idris Suede Tall Boots

Naturalizer Idris Suede Tall Boots

Kelli Suede Tall Boots

Kelli Suede Tall Boots

Lauren Ralph Lauren Kelli Suede Tall Boots

Valora Suede Block Heel Tall Boots

Valora Suede Block Heel Tall Boots

Vionic Valora Suede Block Heel Tall Boots

Cassidie Waterproof Suede Low Heel Booties

Cassidie Waterproof Suede Low Heel Booties

Blondo Cassidie Waterproof Suede Low Heel Booties

Permanently Reduced

Thea Suede Tall Boots

Thea Suede Tall Boots

Born Thea Suede Tall Boots

Permanently Reduced

Timmy Leather Kitten Heel Tall Boots

Timmy Leather Kitten Heel Tall Boots

Franco Sarto Timmy Leather Kitten Heel Tall Boots

$ 169.99 - $ 250.00

Internet Exclusive

Francesca Leather Kitten Heel Ankle Booties

Francesca Leather Kitten Heel Ankle Booties

Bruno Magli Francesca Leather Kitten Heel Ankle Booties

Internet Exclusive

Taylin Suede Kitten Heel Tall Dress Boots

Taylin Suede Kitten Heel Tall Dress Boots

Sam Edelman Taylin Suede Kitten Heel Tall Dress Boots

Permanently Reduced

Sharnell Heel Leather Adjustable Waterproof Western Inspired Boots

Sharnell Heel Leather Adjustable Waterproof Western Inspired Boots

Sofft Sharnell Heel Leather Adjustable Waterproof Western Inspired Boots

Permanently Reduced

Tyrell Leather Block Heel Tall Dress Boots

Tyrell Leather Block Heel Tall Dress Boots

Gianni Bini Tyrell Leather Block Heel Tall Dress Boots

Dillard´s Exclusive

Hailey Suede Buckle Hardware Block Heel Booties

Hailey Suede Buckle Hardware Block Heel Booties

TOMS Hailey Suede Buckle Hardware Block Heel Booties

Permanently Reduced

Internet Exclusive

Only size 9 available

Anny Leather Block Heel Platform Tall Boots

Anny Leather Block Heel Platform Tall Boots

Kork-Ease Anny Leather Block Heel Platform Tall Boots

Idris Leather Tall Boots

Idris Leather Tall Boots

Naturalizer Idris Leather Tall Boots

Aime Leather Platform Block Heel Booties

Aime Leather Platform Block Heel Booties

Kork-Ease Aime Leather Platform Block Heel Booties

Wheron Suede Tall Boots

Wheron Suede Tall Boots

Gentle Souls Wheron Suede Tall Boots

Tara Block Heel Suede Western Inspired Booties

Tara Block Heel Suede Western Inspired Booties

Sofft Tara Block Heel Suede Western Inspired Booties

Permanently Reduced

Hudsin Suede Tall Boots

Hudsin Suede Tall Boots

Dolce Vita Hudsin Suede Tall Boots

Women's Kasey Virginia Leather Heeled Tall Boots

Women's Kasey Virginia Leather Heeled Tall Boots

Dr. Martens Women's Kasey Virginia Leather Heeled Tall Boots

Only size 5, 11 available

Deion Suede Square Toe Block Heel Tall Boots

Deion Suede Square Toe Block Heel Tall Boots

Gianni Bini Deion Suede Square Toe Block Heel Tall Boots

Dillard´s Exclusive

Sergey Suede Stiletto Booties

Sergey Suede Stiletto Booties

Gianni Bini Sergey Suede Stiletto Booties

Dillard´s Exclusive

Esther Sueded Fabric Kitten Heel Mid Calf Boots

Esther Sueded Fabric Kitten Heel Mid Calf Boots

Matisse Esther Sueded Fabric Kitten Heel Mid Calf Boots

Summit Suede Buckle Hardware Platform Block Heel Booties

Summit Suede Buckle Hardware Platform Block Heel Booties

Steve Madden Summit Suede Buckle Hardware Platform Block Heel Booties

Ariana Suede Kitten Heel Tall Boots

Ariana Suede Kitten Heel Tall Boots

Dolce Vita Ariana Suede Kitten Heel Tall Boots

Permanently Reduced

Talina Suede Slouch Boots

Talina Suede Slouch Boots

Dolce Vita Talina Suede Slouch Boots

Internet Exclusive

Only size 7.5 available

Weslye Suede Snip Toe Kitten Block Heel Boots

Weslye Suede Snip Toe Kitten Block Heel Boots

Gianni Bini Weslye Suede Snip Toe Kitten Block Heel Boots

Dillard´s Exclusive

Loralie Cashmere Suede Whipstitch Kitten Heel Ankle Boots

Loralie Cashmere Suede Whipstitch Kitten Heel Ankle Boots

Ron White Loralie Cashmere Suede Whipstitch Kitten Heel Ankle Boots

Prizelle Suede Tall Boots

Prizelle Suede Tall Boots

Alex Marie Prizelle Suede Tall Boots

Dillard´s Exclusive

Stasia Leather Kitten Heel Dress Booties

Stasia Leather Kitten Heel Dress Booties

Steve Madden Stasia Leather Kitten Heel Dress Booties

Judgement Leather Block Heel Combat Booties

Judgement Leather Block Heel Combat Booties

Bed Stu Judgement Leather Block Heel Combat Booties

Internet Exclusive

Tyrell Tumbled Leather Block Heel Tall Dress Boots

Tyrell Tumbled Leather Block Heel Tall Dress Boots

Gianni Bini Tyrell Tumbled Leather Block Heel Tall Dress Boots

Dillard´s Exclusive

Tayla Suede Tall Boots

Tayla Suede Tall Boots

Dune London Tayla Suede Tall Boots

Internet Exclusive

Florish Stretch Square Toe Block Heel Tall Boots

Florish Stretch Square Toe Block Heel Tall Boots

Donald Pliner Florish Stretch Square Toe Block Heel Tall Boots

Irvin Stretch Ruched Velvet Block Heel Booties

Irvin Stretch Ruched Velvet Block Heel Booties

Gianni Bini Irvin Stretch Ruched Velvet Block Heel Booties

Dillard´s Exclusive

Isabeau Suede Knee High Boots

Isabeau Suede Knee High Boots

Naturalizer Isabeau Suede Knee High Boots

Permanently Reduced

Jaycen Suede Tall Boots

Jaycen Suede Tall Boots

Franco Sarto Jaycen Suede Tall Boots

Permanently Reduced

Internet Exclusive

Gibi Suede Tall Boots

Gibi Suede Tall Boots

Vince Camuto Gibi Suede Tall Boots

Permanently Reduced

Yule Suede Bow Block Heel Booties

Yule Suede Bow Block Heel Booties

Copper Key Yule Suede Bow Block Heel Booties

Dillard´s Exclusive

Seravina Waterproof Suede Kitten Heel Booties

Seravina Waterproof Suede Kitten Heel Booties

Blondo Seravina Waterproof Suede Kitten Heel Booties

Permanently Reduced

Internet Exclusive

Hailey Water Resistant Leather Block Heel Booties

Hailey Water Resistant Leather Block Heel Booties

TOMS Hailey Water Resistant Leather Block Heel Booties

Adele Suede Tall Boots

Adele Suede Tall Boots

kate spade new york Adele Suede Tall Boots

Internet Exclusive

Dazha Leather Kitten Heel Dress Booties

Dazha Leather Kitten Heel Dress Booties

Donald Pliner Dazha Leather Kitten Heel Dress Booties

Permanently Reduced

Internet Exclusive

Patrese Leather Pointed Toe Kitten Heel Dress Booties

Patrese Leather Pointed Toe Kitten Heel Dress Booties

Naturalizer Patrese Leather Pointed Toe Kitten Heel Dress Booties

Travers Suede Block Heel Over The Knee Boots

Travers Suede Block Heel Over The Knee Boots

Gianni Bini Travers Suede Block Heel Over The Knee Boots

Dillard´s Exclusive

Virona H2O Leather Tall Block Heel Boots

Virona H2O Leather Tall Block Heel Boots

Dolce Vita Virona H2O Leather Tall Block Heel Boots

Demi Leather Stack Heel Booties

Demi Leather Stack Heel Booties

Lauren Ralph Lauren Demi Leather Stack Heel Booties

Women's Dixon Leather Block Heel Western Booties

Women's Dixon Leather Block Heel Western Booties

Ariat Women's Dixon Leather Block Heel Western Booties

Women's Leona Farrier Leather Platform Heel Combat Boots

Women's Leona Farrier Leather Platform Heel Combat Boots

Dr. Martens Women's Leona Farrier Leather Platform Heel Combat Boots

Permanently Reduced

Only size 6, 7 available

Virona H2O Suede Tall Block Heel Boots

Virona H2O Suede Tall Block Heel Boots

Dolce Vita Virona H2O Suede Tall Block Heel Boots

Cecily Waterproof Leather Tall Boots

Cecily Waterproof Leather Tall Boots

Sofft Cecily Waterproof Leather Tall Boots

Darnold Leather Block Heel Booties

Darnold Leather Block Heel Booties

Gianni Bini Darnold Leather Block Heel Booties

Dillard´s Exclusive

Isabella Leather Western Booties

Isabella Leather Western Booties

Justin Boots Isabella Leather Western Booties

Internet Exclusive

Irvin Stretch Faux Leather Block Heel Booties

Irvin Stretch Faux Leather Block Heel Booties

Gianni Bini Irvin Stretch Faux Leather Block Heel Booties

Dillard´s Exclusive

Virgee Suede Slouch Shaft Kitten Heel Mid Calf Boots

Virgee Suede Slouch Shaft Kitten Heel Mid Calf Boots

ASH Virgee Suede Slouch Shaft Kitten Heel Mid Calf Boots

Irvin Stretch Block Heel Booties

Irvin Stretch Block Heel Booties

Gianni Bini Irvin Stretch Block Heel Booties

Dillard´s Exclusive

Taylin Leather Kitten Heel Tall Dress Boots

Taylin Leather Kitten Heel Tall Dress Boots

Sam Edelman Taylin Leather Kitten Heel Tall Dress Boots

Permanently Reduced

Charleston Stretch Kitten Heel Dress Booties

Charleston Stretch Kitten Heel Dress Booties

Jack Rogers Charleston Stretch Kitten Heel Dress Booties

Lytton Leather Mid Kitten Heel Boots

Lytton Leather Mid Kitten Heel Boots

Steve Madden Lytton Leather Mid Kitten Heel Boots

Permanently Reduced

186 Items
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About Comfortable Heeled Boots

Discover the perfect blend of style and comfort with our collection of comfortable heeled boots. Designed for all-day wear, these boots feature cushioned insoles and supportive designs that elevate your look without sacrificing comfort. Whether you're dressing up for a night out or adding flair to your everyday outfit, these versatile boots are a must-have.

Crafted from high-quality materials, our comfortable heeled boots offer durability and a chic aesthetic. With various styles, including block heels and sleek silhouettes, you can easily find the ideal pair to complement any wardrobe. Step confidently into any occasion with boots that provide both elegance and ease.

Celebrate the spirit of the season with Dillard's. From timeless treasures to thoughtful gifts, discover pieces for your wife, husband, kids, parents, and all your loved ones this Christmas Holiday 2025.

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