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Top Callaway Apparel Deals for September 2025

The biggest price drops from Callaway Apparel over the past 30 days.

Perry Ellis Men's Chris Boots in Cognac/Brown, Siz...

A stylish men's chelsea boot with a squared toe. The dual elastic shaft and pull tab make this boot easy to slide on the foot. The sock lining covers a dense foam foot bed for extra comfort. The combination outsole provides a non-slip feature under the ball of the foot for traction. Pull Tab and Double Gore for Easy On/Off Grooved Outsole for Added Traction Foam Insole for Added Comfort Faux Leather 1" Heel Imported | Perry Ellis Men's Chris Boots in Cognac/Brown, Size 9, Faux Leather, Solid, Regular
$125.00
$34.9772% OFF

Perry Ellis Men's Chris Boots in Cognac/Brown, Siz...

A stylish men's chelsea boot with a squared toe. The dual elastic shaft and pull tab make this boot easy to slide on the foot. The sock lining covers a dense foam foot bed for extra comfort. The combination outsole provides a non-slip feature under the ball of the foot for traction. Pull Tab and Double Gore for Easy On/Off Grooved Outsole for Added Traction Foam Insole for Added Comfort Faux Leather 1" Heel Imported | Perry Ellis Men's Chris Boots in Cognac/Brown, Size 8.5, Faux Leather, Solid, Regular
$125.00
$34.9772% OFF

Perry Ellis Men's Trent Boots in Black, Size 8.5, ...

The Trent Casual Boot in black from Perry Ellis is a versatile and comfortable men's footwear choice. Its sleek black design pairs effortlessly with various outfits, making it a wardrobe essential. The boot's durable construction ensures long-lasting wear, while the comfortable lining provides all-day comfort. Whether you're heading to work or out for a casual outing, the Trent Casual Boot in black is the perfect choice for stylish and practical footwear. Experience unparalleled comfort with our Ultra Foam insole, providing all-day cushioning and support Features two zippers: one functional for secure closure and one ornamental for added style Sleek Black Design That Pairs Effortlessly With Various Outfits Durable Construction For Long-Lasting Wear Comfortable Lining For All-Day Comfort All-Weather Grip-Tread Sole Faux Leather Boot Round Toe Shape True to Size Fit Regular Fit Imported | Perry Ellis Men's Trent Boots in Black, Size 8.5, Regular
$125.00
$35.0072% OFF

Perry Ellis Men's Chris Boots in Cognac/Brown, Siz...

A stylish men's chelsea boot with a squared toe. The dual elastic shaft and pull tab make this boot easy to slide on the foot. The sock lining covers a dense foam foot bed for extra comfort. The combination outsole provides a non-slip feature under the ball of the foot for traction. Pull Tab and Double Gore for Easy On/Off Grooved Outsole for Added Traction Foam Insole for Added Comfort Faux Leather 1" Heel Imported | Perry Ellis Men's Chris Boots in Cognac/Brown, Size 11, Faux Leather, Solid, Regular
$125.00
$35.0072% OFF

Perry Ellis Men's Trent Boots in Black, Size 10, R...

The Trent Casual Boot in black from Perry Ellis is a versatile and comfortable men's footwear choice. Its sleek black design pairs effortlessly with various outfits, making it a wardrobe essential. The boot's durable construction ensures long-lasting wear, while the comfortable lining provides all-day comfort. Whether you're heading to work or out for a casual outing, the Trent Casual Boot in black is the perfect choice for stylish and practical footwear. Experience unparalleled comfort with our Ultra Foam insole, providing all-day cushioning and support Features two zippers: one functional for secure closure and one ornamental for added style Sleek Black Design That Pairs Effortlessly With Various Outfits Durable Construction For Long-Lasting Wear Comfortable Lining For All-Day Comfort All-Weather Grip-Tread Sole Faux Leather Boot Round Toe Shape True to Size Fit Regular Fit Imported | Perry Ellis Men's Trent Boots in Black, Size 10, Regular
$125.00
$35.0072% OFF

Perry Ellis Men's Trent Boots in Black, Size 9.5, ...

The Trent Casual Boot in black from Perry Ellis is a versatile and comfortable men's footwear choice. Its sleek black design pairs effortlessly with various outfits, making it a wardrobe essential. The boot's durable construction ensures long-lasting wear, while the comfortable lining provides all-day comfort. Whether you're heading to work or out for a casual outing, the Trent Casual Boot in black is the perfect choice for stylish and practical footwear. Experience unparalleled comfort with our Ultra Foam insole, providing all-day cushioning and support Features two zippers: one functional for secure closure and one ornamental for added style Sleek Black Design That Pairs Effortlessly With Various Outfits Durable Construction For Long-Lasting Wear Comfortable Lining For All-Day Comfort All-Weather Grip-Tread Sole Faux Leather Boot Round Toe Shape True to Size Fit Regular Fit Imported | Perry Ellis Men's Trent Boots in Black, Size 9.5, Regular
$125.00
$35.0072% OFF

Perry Ellis Men's Chris Boots in Cognac/Brown, Siz...

A stylish men's chelsea boot with a squared toe. The dual elastic shaft and pull tab make this boot easy to slide on the foot. The sock lining covers a dense foam foot bed for extra comfort. The combination outsole provides a non-slip feature under the ball of the foot for traction. Pull Tab and Double Gore for Easy On/Off Grooved Outsole for Added Traction Foam Insole for Added Comfort Faux Leather 1" Heel Imported | Perry Ellis Men's Chris Boots in Cognac/Brown, Size 8, Faux Leather, Solid, Regular
$125.00
$35.0072% OFF

Perry Ellis Men's Kelce Dress Shoes in Black, Size...

The Kelce Dress Shoe from Perry Ellis is a classic and versatile footwear choice for any formal occasion. Crafted with high-quality materials, this shoe features a timeless design, a secure lace-up closure, and a polished finish that adds a touch of sophistication. Whether you're attending a wedding, a business meeting, or another special event, the Kelce Dress Shoe is the perfect way to elevate your attire. Regular Fit Faux Leather Ultra Foam Insole Round Toe Shape Lace up Closure Wax Round Laces Imported | Perry Ellis Men's Kelce Dress Shoes in Black, Size 8, Faux Leather, Regular
$100.00
$29.9770% OFF

Perry Ellis Men's Kelce Dress Shoes in Black, Size...

The Kelce Dress Shoe from Perry Ellis is a classic and versatile footwear choice for any formal occasion. Crafted with high-quality materials, this shoe features a timeless design, a secure lace-up closure, and a polished finish that adds a touch of sophistication. Whether you're attending a wedding, a business meeting, or another special event, the Kelce Dress Shoe is the perfect way to elevate your attire. Regular Fit Faux Leather Ultra Foam Insole Round Toe Shape Lace up Closure Wax Round Laces Imported | Perry Ellis Men's Kelce Dress Shoes in Black, Size 9.5, Faux Leather, Regular
$100.00
$29.9770% OFF

Perry Ellis Men's Stride Sneakers in Bright White,...

Step into classic cool with these men's retro-inspired sneakers. Featuring a timeless runner silhouette with distinctive textured paneling, these sneakers offer a versatile athletic edge for your everyday look. Faux Suede Contrast Detail Embossed Logo Detail Athletic Silhouette Rubber Sole | Perry Ellis Men's Stride Sneakers in Bright White, Size 9.5, Regular
$100.00
$29.9870% OFF

Perry Ellis Men's Stride Sneakers in Black, Size 1...

Step into classic cool with these men's retro-inspired sneakers. Featuring a timeless runner silhouette with distinctive textured paneling, these sneakers offer a versatile athletic edge for your everyday look. Faux Suede Contrast Detail Embossed Logo Detail Athletic Silhouette Rubber Sole | Perry Ellis Men's Stride Sneakers in Black, Size 11, Regular
$100.00
$29.9870% OFF

Perry Ellis Men's Slick Cap Toe Slip-On in Black, ...

Memory Foam Insole Rubber Outsole Faux Leather Square Toe Regular Fit Slip On Imported | Perry Ellis Men's Slick Cap Toe Slip-On in Black, Size 10, Faux Leather, Regular
$115.00
$35.0070% OFF

Perry Ellis Men's Slick Cap Toe Slip-On in Black, ...

Memory Foam Insole Rubber Outsole Faux Leather Square Toe Regular Fit Slip On Imported | Perry Ellis Men's Slick Cap Toe Slip-On in Black, Size 12, Faux Leather, Regular
$115.00
$35.0070% OFF

Perry Ellis Men's Slick Cap Toe Slip-On in Black, ...

Memory Foam Insole Rubber Outsole Faux Leather Square Toe Regular Fit Slip On Imported | Perry Ellis Men's Slick Cap Toe Slip-On in Black, Size 9.5, Faux Leather, Regular
$115.00
$35.0070% OFF

Perry Ellis Men's Slick Cap Toe Slip-On in Black, ...

Memory Foam Insole Rubber Outsole Faux Leather Square Toe Regular Fit Slip On Imported | Perry Ellis Men's Slick Cap Toe Slip-On in Black, Size 8, Faux Leather, Regular
$115.00
$35.0070% OFF

Perry Ellis Men's Slick Cap Toe Slip-On in Black, ...

Memory Foam Insole Rubber Outsole Faux Leather Square Toe Regular Fit Slip On Imported | Perry Ellis Men's Slick Cap Toe Slip-On in Black, Size 7.5, Faux Leather, Regular
$115.00
$35.0070% OFF

Perry Ellis Men's Slick Cap Toe Slip-On in Black, ...

Memory Foam Insole Rubber Outsole Faux Leather Square Toe Regular Fit Slip On Imported | Perry Ellis Men's Slick Cap Toe Slip-On in Black, Size 10.5, Faux Leather, Regular
$115.00
$35.0070% OFF

Perry Ellis Men's Slick Cap Toe Slip-On in Black, ...

Memory Foam Insole Rubber Outsole Faux Leather Square Toe Regular Fit Slip On Imported | Perry Ellis Men's Slick Cap Toe Slip-On in Black, Size 8.5, Faux Leather, Regular
$115.00
$35.0070% OFF

Perry Ellis Men's Slick Cap Toe Slip-On in Black, ...

Memory Foam Insole Rubber Outsole Faux Leather Square Toe Regular Fit Slip On Imported | Perry Ellis Men's Slick Cap Toe Slip-On in Black, Size 11.5, Faux Leather, Regular
$115.00
$35.0070% OFF

Perry Ellis Men's Slick Cap Toe Slip-On in Black, ...

Memory Foam Insole Rubber Outsole Faux Leather Square Toe Regular Fit Slip On Imported | Perry Ellis Men's Slick Cap Toe Slip-On in Black, Size 13, Faux Leather, Regular
$115.00
$35.0070% OFF

Perry Ellis Men's Faux Leather Oxford Pattent Shoe...

These Perry Ellis men's patent leather shoes are the perfect choice for a range of occasions from business meetings to formal events. The classic Oxford design makes it easy to style these men's dress shoes up or down as needed. Plus, the patent finish adds a sleek touch that keeps your look on point. Regular Fit Patent Leather-Like Material For A Sleek And Formal Look Oxford Design For A Timeless Look Laced Imported | Perry Ellis Men's Faux Leather Oxford Pattent Shoes in Black, Size 10, Regular
$128.00
$39.9769% OFF

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