Free Shipping when you spend $99 or more. Details. Shop >
Sears.ca> Outlet> Shoes> Women> Boots>  Casual
Sort by
Display per Page

Attitude /MD 'Finolano' Wedge Bootie

Attitude /MD 'Finolano' Wedge Bootie

  • The Finolano wedge is a great wedged bootie with great gold detail.

    WEBCODE: W- 5445275

Clearance-save 70%$28.94

Clarks Women's 'Whistle Ballad' Leather Ankle Boot

Clarks Women's 'Whistle Ballad' Leather Ankle... Boot

  • Need something to boot around town in? 'Whistle Ballad' is made for strolling the mall, neighbourhood walks and weekend fun. Wherever you're off to, the Ortholite footbed will cushion your every step.

Click for SavingsFrom $52.94

Wanted Women's 'Sadler' Microfibre Boot

Wanted Women's 'Sadler' Microfibre Boot

34 reviews

  • Put fashion at your feet in this street-ready suede-look boot. The 15'' shaft with triple-buckle detail ceates a long, lean leggy look. The lug outsole provides superb traction for when the weather gets cold and slippery.

Further Reduced-save 70%$22.94

Barbo Women's 'Claudia' Suede Leather Boot

Barbo Women's 'Claudia' Suede Leather Boot

  • One of the season's hottest trends gets a major refinement for everyday wear. With just a touch of moccasin styling, these gorgeous suede leather boots are perfect for casual wear any day of the week. They're lined in cozy fleece and faux shearling so they'll keep you warm while being right on trend.

Clearance-save 70%$43.94

Hush Puppies 'Kana' Leather Ankle Boot

Hush Puppies 'Kana' Leather Ankle Boot

1 review

  • Step up to great style in these cute waterproof boots! Classic styling with buckle details for a fashionable look, while still keeping your feet warm and dry. Soft, felt insoles and warm Mintex lining cushion your every step and get you through winter in comfort and style.

Clearance-save 40%$83.94

JESSICA /MD 'Kluvac' Tall Boot With Chunky Heel

JESSICA /MD 'Kluvac' Tall Boot With Chunky He...el

1 review

  • The must have Fall boot, goes great with any outfit!

    WEBCODE: W- 5444483

Clearance-save 70%$27.94

Foothrills by Clinic Pant Boots-Morgan

Foothrills by Clinic Pant Boots-Morgan

  • CATALOGUE/ONLINE EXCLUSIVE
  • tricot lining
  • 3 3/4'' shaft

Clearance-save 65%$50.94

Clarks Women's 'Saddle Ride' Leather Slouch Boot

Clarks Women's 'Saddle Ride' Leather Slouch B...oot

  • This eye catching style is embellished with a cozy faux fur cuff and side trim, and wrapped with a knotted strap. Made from premium leather, this boot features an OrthoLite® footbed and great wedge heel that cushions each step in comfort. Wear this chic boot over tights with a mini or with leggings or skinny jeans.

Click for Savings$191.94

Henri Pierre 'Ghita' aquaskin™ Women's Waterproof Boots

Henri Pierre 'Ghita' aquaskin™ Women's Waterp...roof Boots

  • Here is a boot that will put a little zip into any street look. Ruching on the forefoot and cool buckling detail combine with a sensible heel and waterproof protection to make this your go-to casual style.

Clearance-save 70%$42.94

Martino Equestrian Style Leather/Waterproof Boot For Women

Martino Equestrian Style Leather/Waterproof B...oot For Women

14 reviews

  • Have it all... elegant, trend-worthy style, rich genuine leather, made in Canada and waterproof to boot.

Clearance-save 75%$57.94

Henri Pierre 'Babeth' aquaskin™ Women's Waterproof Boots

Henri Pierre 'Babeth' aquaskin™ Women's Water...proof Boots

2 reviews

  • Kick your style into gear with this chic, grommet-detailed boot. It's the perfect accompaniment to this season's moto jackets or a trendy bomber... just tuck in your skinnies.

Clearance-save 70%$42.94

Clarks Women's 'Alpine Bonnet' Leather Boot

Clarks Women's 'Alpine Bonnet' Leather Boot

  • High style in a mix of rich, polished leather and velvety suede. This women's tall boot is finished with an inside zip for easy on/off plus a decorative outside zip, cinch strap at the ankle, and chunky stacked heel. An OrthoLite® insole cushions every step. Make a statement in this stylish leather and suede boot in dark brown.

Clearance-save 70%$81.94

Nevada /MD 'Sigman' Short Bootie

Nevada /MD 'Sigman' Short Bootie

  • Short, fun bootie. Great for casual days.

    WEBCODE: W- 5447171

Clearance$20.94

Alia Women's Strap/Gore Detailed Bootie

Alia Women's Strap/Gore Detailed Bootie

3 reviews

  • With jeans, trousers and dress pants, these cute ankle boots are anything but short on style. They're fabulously detailed and comfortable to boot, so you can wear them for your commute to work and keep them on when you get there. They're even a great casual choice on the weekend too.

Clearance-save 70%$16.94

Henri Pierre Women's 'Kaissa' Waterproof Suede Leather Boots

Henri Pierre Women's 'Kaissa' Waterproof Sued...e Leather Boots

1 review

  • The natural comfort of leather and the stylish look of suede make this waterproof boot the perfect choice for the office or those casual evenings out on the town. Soft cushioning will cradle your every step and the 14'' high shaft on this design will give you even more to love this winter!

Clearance-save 65%$62.94

JESSICA /MD Women's 'Codi' Riding Boot

JESSICA /MD Women's 'Codi' Riding Boot

  • You win the style stakes with this equestrian-inspired tall boot. Authentic details like side pull tabs and an easy-walking heel mean you'll take every outfit in stride.

Click for Savings$59.94

Henri Pierre Women's 'Pakita' Waterproof Leather Riding Boot

Henri Pierre Women's 'Pakita' Waterproof Leat...her Riding Boot

12 reviews

  • Tall, sleek and chic, riding-style boots are a must-have for this season and beyond. Waterproof and detailed with trendy buckle and strap, these boots are easily dressed up or down and can dramatically change the look of an entire outfit.

Clearance-save 75%$59.94

St.Emile™ Women's 13'' Inside-Zip Leather Fashion Boot

St.Emile™ Women's 13'' Inside-Zip Leather Fas...hion Boot

2 reviews

  • Fashion on the go. Elasticized side gores and inside zip closure help make this full-grain leather boot easy to slide on and off.

Clearance-save 55%$76.94

Clarks Women's 'Christine Chill' Leather Bootie

Clarks Women's 'Christine Chill' Leather Boot...ie

  • A braided leather inset adds a stylish touch to this comfortable women's ankle boot. Made from soft leather, it features a cushioned footbed and lightweight outsole for walking ease. Wear it with rolled-up jeans, tights or cropped pants that show off its attractive braided detail.

    WEBCODE: W- 5410341

Click for Savings$46.94

JESSICA /MD Women's 'Veprek' Suede Fashion Boot

JESSICA /MD Women's 'Veprek' Suede Fashion Bo...ot

1 review

  • Look long, lean and luscious in these genuine suede boots. A simple and clean design, these boots send your look sky high whether paired with great leggings or a long flowing skirt.

Clearance-save 65%$46.94

Nevada /MD 'Kosike' Moto Boot With Double Buckle

Nevada /MD 'Kosike' Moto Boot With Double Buc...kle

  • The Kosike is a great boot with edge. Get 'the look' for Fall!

    WEBCODE: W- 5447160

Clearance-save 70%$23.94

Henri Pierre 'Carmel' Waterproof Suede Leather Winter Boot For Women

Henri Pierre 'Carmel' Waterproof Suede Leathe...r Winter Boot For Women

7 reviews

  • Now you can enjoy the style of suede with the worry-free benefits of water-proofing in this winter boot from Henri Pierre. Waterproof to the zipper the 'Carmel' boot also has fleece lining to keep you warm as well as dry.

Clearance-save 75%$49.94

Martino Women's Waterproof Suede Fringe Ankle Boot

Martino Women's Waterproof Suede Fringe Ankle... Boot

1 review

  • Warm and dry on the inside, tres chic on the outside. These luxurious suede-leather boots feature flirty fringe at the ankles for added flair.

Clearance-save 65%From $45.94

NYC Couture Women's Over-The-Knee Boot

NYC Couture Women's Over-The-Knee Boot

  • Tall, sleek and chic, riding-style boots are a must-have for the season and beyond. Detailed with trendy straps and buckles these boots are easily dressed up or down and can dramatically change the look of an entire outfit.

Clearance-save 75%$23.94