Free Shipping when you spend $49 or more. Details. Shop >
Sears.ca> Outlet> Shoes> Men>  $50 - $99
Sort by
Display per Page

Boulevard Club Men's Lunch Time Clean Toe Cap Dress Shoe

Boulevard Club Men's Lunch Time Clean Toe Cap... Dress Shoe

  • The men's lunch time clean toe cap dress shoe is the perfect style for the office. With its leather upper and classic style, these shoes will be an instant favourite.

Further Reduced-save 30%$76.94

Logan Hill™ 'Jackson' Open Toe Slide

Logan Hill™ 'Jackson' Open Toe Slide

  • The 'Jackson' Open Toe Slide is ready for the upcoming season. This shoe is ready to be slipped on quickly and paired with any outfit. Whether its for a day outdoors or a day of errands, this slip on style is ready when you are

Further Reduced-save 40%$51.94

Logan Hill™  'Gabriel' Sport Sandal

Logan Hill™ 'Gabriel' Sport Sandal

  • This new Sport Sandal from LOGAN HILL is perfect for the upcoming season. Its open style will allow your feet to take in the warmer air while being easy to slip on and off.

Further Reduced-save 40%$51.94

Clarks Men's 'Rattlin Port' Shoe

Clarks Men's 'Rattlin Port' Shoe

  • Add a laid-back vibe to your day with this contemporary-styled leather slip-on. Features a breathable mesh insole and EVA outsole for cool comfort and flexible, lightweight cushioning.

Clearance-save 40%$50.94

Clarks Men's 'Senner Falls' Slip-On

Clarks Men's 'Senner Falls' Slip-On

  • Designed for comfort and style, the low-cut shoe delivers a great everyday look. Comfortably styled with a breathable leather upper and twin gores for a snug, secure fit. Perfect for work or play.

Further Reduced-save 45%$71.94

Saucony Men's 'Ignition 4' Running Shoe

Saucony Men's 'Ignition 4' Running Shoe

  • Perfect for runners, this performance shoe features an IMEVA insole and XT600 outsole for superb cushioning while you walk or run. Breathable mesh design makes every step cool and comfortable. The padded insole is removable so you can add orthotics when needed.

Clearance-save 20%$79.94

Clarks 'Boid Knoll' Casual Slip-On Shoe For Men

Clarks 'Boid Knoll' Casual Slip-On Shoe For M...en

  • Cool, casual and always a great choice for work and weekend wear too, these deck-style shoes are perfect with chinos, denim, shorts and trousers. They're super comfortable and have a classic look that's always in style.

Clearance-save 40%$61.94

Logan Hill™ 'John' Closed Toe Fisherman Sandal

Logan Hill™ 'John' Closed Toe Fisherman Sanda...l

  • The 'John' Closed Toe Fisherman Sandal is ready for the upcoming season. This shoe is ready to be slipped on quickly and paired with any outfit. Whether its for a day outdoors or a day of errands, this slip on style is ready when you are.

Further Reduced-save 40%$51.94

Hi-Tec™ Men's 'Sierra Lite Original' Suede Hiking Shoe

Hi-Tec™ Men's 'Sierra Lite Original' Suede Hi...king Shoe

  • Enjoy an afternoon on the trails with this comfortable suede hiker with a soft padded collar. The mesh-detailed, suede upper and moisture-wicking lining help keep feet cool and dry. EVA midsole and outsole provide a great double-dose of cushiony comfort. Heavily treaded outsole provides a sure grip on all type of terrains.

Clearance-save 40%$51.94

Propét Men's 'Sullivan' Leather Sandal

Propét Men's 'Sullivan' Leather Sandal

  • Step up your style and comfort level this summer in this smart-looking leather sandal. Features Rejuve Motion Technology and an EVA midsole for support and cushioning throughout the day. Handy toggle lace system helps provide a snug, secure fit.

Clearance-save 40%$50.94

Reebok 'NPC II Classic' Men's Leather Athletic Shoe

Reebok 'NPC II Classic' Men's Leather Athleti...c Shoe

1 review

  • The 'NPC II Classic' is designed to give you a comfortable and worry-free workout. With its soft leather upper, EVA midsole and high-abrasion rubber outsole, it will give you the performance you demand. And it accommodates orthotics to add to your comfort.

Further Reduced-save 30%$51.94

Clarks Men's 'Colson Over' Shoe

Clarks Men's 'Colson Over' Shoe

  • Upgrade your shoe collection with this dressy leather lace-up style. Designed with a breathable leather upper and molded EVA insole for true walking comfort. A classic look that will continue to hold its fashionable appeal for years to come.

Clearance-save 40%$83.94

Clarks Men's 'Girona' Lace-Up

Clarks Men's 'Girona' Lace-Up

3 reviews

  • A classic shoe laces that combines elegance and cushioned comfort. EVA outsole and Ortholite insole will give you hours of comfort, all day, every occasion.

Further Reduced-save 45%$71.94

Arnold Palmer™ Men's Leather Self-Adhesive Strap Shoe

Arnold Palmer™ Men's Leather Self-Adhesive St...rap Shoe

  • Designed with all-day comfort in mind, this versatile style is constructed of leather with a self-adhesive strap for breathability and a snug secure fit. For added walking support and comfort, it has a Texon® midsole and a lightweight outsole. Perfect for long hours on your feet whether at work or play.

Further Reduced-save 45%From $56.94