Top Rockport Deals & Price Drops for December 2025

Our Maverick gives you cool, considered style that gets you where you need to go comfortably. It’s defined by a lug sole, leather upper, and all-day flexibility. Whether you’re pairing it with jeans, khakis, or dressier pants, this classic American casual

The Hennly dress sandal is an epitome of sophisticated style. It offers a block heel and square toe. This sandal will keep you looking chic all-day. This sandal is the perfect wardrobe staple! Featuring truTECH® technology for lightweight shock absorption.

Whether it’s a job interview, wedding, or back-to-office, calendars are filling up. The Style Leader 2 is a no-fuss dress shoe that’s an essential for each of these step-it-up occasions. An EVA outsole helps to reduce foot fatigue so you can walk and stand more comfortably, all day long.

Step into effortless style and all-day comfort with the Rockport Sagey Slingback Ballet Flats. Designed for the modern woman, these chic flats combine a sophisticated square toe and a convenient slip-on silhouette with a flexible, stretchy slingback strap for a perfect, secure fit. What truly sets them apart is the innovative truTECH® technology built into the footbed, providing exceptional lightweight shock absorption that cushions your every step. Whether you're navigating a busy workday, enjoying a weekend brunch, or dancing into the evening, these versatile dress shoes ensure you look polished without sacrificing comfort. The elegant sage hue adds a subtle, refined touch to any outfit, from tailored trousers to flowing dresses. Experience the Rockport difference where premium style meets proven comfort technology, making these ballet flats an essential addition to your wardrobe for any occasion that demands both elegance and ease.

Step into versatile style with the Rockport Classic Break Chukka Boot. This boot shoe masterfully bridges the gap between your professional demands and casual weekend plans, offering a sophisticated profile that works as hard as you do. Crafted from premium leather, it delivers a polished look that pairs effortlessly with denim or complements a tailored jacket and tie. Experience all-day comfort through its thoughtfully designed construction. The lightweight and flexible build moves with you, while a soft knit lining provides a gentle feel against your foot. A cushioning foam footbed offers exceptional support, making these boots ideal for long days on your feet. Discover the perfect balance of durability and modern style. Available in size 16 M, this chukka boot is built for lasting wear without sacrificing an ounce of comfort. It’s more than just footwear; it’s a reliable addition to your wardrobe that understands the need for both function and fashion. Find your new go-to boot at Rockport.com, where quality craftsmanship meets everyday versatility. Elevate your look with a design that’s ready for anything your schedule brings.

Step into effortless comfort and versatile style with the Rockport Jaya Slip-On Sandals. Designed for the man who values both relaxation and a polished look, these casual flats are your new warm-weather essential. Discover the perfect blend of laid-back ease and Rockport’s renowned craftsmanship at rockport.com. The Jaya features a convenient slip-on design that makes getting ready a breeze, perfect for quick errands, beach days, or casual weekends. Its classic criss-cross strap detailing provides a secure and adjustable fit, ensuring your foot stays comfortably in place with every step. We’ve built these sandals around all-day comfort. A generously cushioned insole offers soft support from heel to toe, making them ideal for long walks or standing. The flexible outsole moves naturally with your foot, providing reliable traction on a variety of surfaces. More than just a sandal, the Jaya is a true wardrobe staple. Its clean, versatile silhouette pairs effortlessly with shorts, chinos, or jeans, seamlessly transitioning from a backyard barbecue to a casual lunch with friends. It’s the easygoing style you’ll reach for again and again. Experience the Rockport difference where quality materials and thoughtful design meet everyday value. These sandals are constructed for durability, so you can enjoy their comfort season after season. Upgrade your casual footwear collection with a pair that doesn’t compromise. Find your perfect fit and explore the full range of men’s footwear at Rockport.com. The Jaya Slip-On Sandals deliver the comfort you deserve and the understated style you want, all from a name you trust.

Step into effortless elegance with the Cindy Total Motion Pump from Rockport. Designed for the modern woman who values both style and comfort, this sophisticated dress shoe elevates any professional or formal ensemble. Its sleek slip-on silhouette and refined pointy toe create a timelessly chic look that transitions seamlessly from the boardroom to evening events. What truly sets this pump apart is the exceptional all-day comfort engineered into its design. The interior features a plush, cushioned insole that cradles your foot, providing support through long hours of wear. Rockport’s innovative truTECH technology is integrated into the construction, offering lightweight shock absorption with every step. This means you can move with confidence and ease, free from the fatigue often associated with dress heels. Available in a versatile size 7.5 Wide, this shoe ensures a perfect, accommodating fit. Experience the unique Rockport promise where premium style meets groundbreaking comfort technology. Discover more sophisticated footwear designed for your dynamic life at Rockport.com.

Step out in style and confidence with the Robinsyn Waterproof Plain Toe Oxford from Rockport. This isn't just another dress shoe; it's a masterclass in combining classic elegance with modern, all-weather performance. Designed for the man who values both looks and substance, these oxfords feature a timeless silhouette that transitions seamlessly from the boardroom to evening engagements. We understand that true comfort is essential, which is why we built innovative flexible forefoot support into the design. This technology moves with you, providing exceptional comfort that lasts all day long. Paired with reliable stabilizing features, every step feels secure and supported, reducing fatigue so you can focus on what matters. Don't let unpredictable weather dictate your style. These shoes are engineered for real life, featuring fully waterproof materials and a specialized water-shedding outsole. Whether you're navigating rainy sidewalks or damp mornings, your feet stay dry and your step remains confident. It's the peace of mind you deserve. Discover the perfect blend of sophistication, comfort, and durability. Visit Rockport.com today to explore the Robinsyn collection and find your ideal fit. Experience the Rockport difference where every detail is crafted for your lifestyle, offering premium quality that stands up to your day, no matter what it brings. Elevate your wardrobe with shoes that work as hard as you do.

Step into effortless style and all-day comfort with the Rockport Cacey Casual Oxford. This versatile lace-up shoe is expertly designed for the modern man who values both a polished look and exceptional support. Its clean, almond-toe silhouette offers a refined aesthetic that transitions seamlessly from the office to weekend outings. At Rockport, we believe your footwear should work as hard as you do. The Cacey is built with our innovative truTECH technology, providing lightweight shock absorption with every step. This means you can stay on your feet longer without the usual fatigue, making these shoes a perfect companion for your everyday adventures. We’ve paired this advanced cushioning with a soft, padded insole for an immediate feeling of comfort right out of the box. The classic lace-up design ensures a secure, personalized fit for your size 11 W foot. Discover the perfect blend of form and function. Visit Rockport.com today to explore our full collection of men's casual shoes and experience the quality craftsmanship that defines our brand. The Cacey Oxford isn't just a shoe; it's your new go-to for reliable, stylish comfort.

Step into effortless style and all-day comfort with the Lance casual loafers from Rockport. Designed for the modern man, these slip-on loafers combine a sleek, versatile silhouette with the trusted support Rockport is known for. Perfect for your daily routine, they transition seamlessly from casual outings to relaxed office settings. Experience the innovative truTECH technology built into every step. This advanced feature provides exceptional lightweight shock absorption, cushioning your feet and reducing fatigue whether you're running errands or enjoying a weekend stroll. The comfortable footbed welcomes you from the moment you put them on, offering a fit that feels broken-in from day one. We understand the importance of personalized support. That's why these men's casual shoes are thoughtfully designed to be orthotic friendly, allowing you to insert your own custom insoles for a perfect, tailored fit. The generous size 13 W width ensures ample room and comfort for those who need it. Crafted with meticulous attention to detail, the Lance loafers are more than just shoes; they're a reliable foundation for your wardrobe. Discover the perfect blend of form and function. Visit Rockport.com today to refresh your footwear collection with a pair that prioritizes your comfort without compromising on style.

Step into effortless style and all-day comfort with the Rockport Whit Dress Slip-On Loafers. Designed for the modern man, these classic bit loafers seamlessly blend timeless sophistication with the innovative comfort technology Rockport is known for. They are the perfect versatile shoe, ready to elevate your casual Friday look or complement your weekend wardrobe with polished ease. The secret to their exceptional wearability lies in the advanced truTECH® technology integrated into the design. This provides lightweight shock absorption with every step, transforming a classic silhouette into a shoe built for real life. Your feet will appreciate the cushioned insole that offers support from morning to night, whether you're navigating the workday or enjoying a relaxed evening out. We've refined the traditional loafer with a clean, ornamented detail that adds a touch of refined character without being overstated. The convenient slip-on design makes them incredibly easy to wear, offering a sleek profile that pairs perfectly with chinos, dark denim, or tailored trousers. This is more than just a shoe; it's a foundation for confident, comfortable style. Experience the Rockport difference where classic design meets modern innovation. Discover the full collection of men's footwear designed for uncompromising comfort and style at Rockport.com. Invest in a wardrobe staple that doesn't ask you to choose between looking good and feeling great—the Whit loafers deliver both.

Step into effortless style and all-day comfort with the Lance casual slip-on loafers from Rockport. Designed for the modern man, these shoes blend a sleek, versatile silhouette with the trusted support Rockport is known for, making them a perfect choice for your daily routine. Experience the innovative truTECH technology that provides exceptional lightweight cushioning and shock absorption with every step. Your feet will feel energized from morning to evening, whether you're running errands, heading to the office, or enjoying a weekend outing. The Lance loafers feature a comfortable, built-in footbed that cradles your foot, offering immediate comfort right out of the box. Their convenient slip-on design means you can get ready and go in seconds without sacrificing a polished look. We've crafted these shoes to be orthotic friendly, giving you the flexibility to use your own custom insoles for personalized support. Available in a size 10.5 Wide, they provide the perfect fit for those needing extra room. Built with Rockport's commitment to quality, these durable casual shoes are made to last season after season. Discover the ideal blend of function and fashion. Visit Rockport.com today to refresh your wardrobe with the Lance loafers, where premium comfort meets everyday style.

Step into superior comfort and style with the Northfield Plain Toe Boot from Rockport. This versatile men's boot is engineered for the demands of your daily life, seamlessly transitioning from a professional business casual environment to your weekend adventures. Its rugged yet refined exterior ensures you look polished and prepared for any setting. Experience the confidence of dry feet with our advanced Hydro-Shield waterproof construction, a core feature designed to protect you from the elements. Beyond staying dry, these boots are built for enduring comfort. The integrated truTECH sport technology provides exceptional cushioning and support from morning until night. We've also prioritized reducing fatigue during long hours on your feet. The lightweight EVA outsole works to minimize impact on your feet and legs, making these boots a smart choice for all-day wear. Discover the perfect blend of durability, weather-ready performance, and innovative comfort that Rockport is known for. Find your ideal fit and explore our full collection of premium footwear at Rockport.com. The Northfield Waterproof Boot represents our commitment to quality craftsmanship and modern functionality, offering a reliable foundation for every step you take.

Step into effortless style and all-day comfort with the Rockport Lyall Slip-on Boat Shoe. Designed for the modern man who values both sophistication and ease, this shoe eliminates the need for laces with its convenient slip-on design, making it your perfect go-to for busy days. The classic almond-shaped toe offers a polished, versatile look that transitions seamlessly from casual weekends to relaxed office settings. Experience exceptional comfort thanks to Rockport's innovative truTECH technology, which provides lightweight cushioning and superior shock absorption with every step. Your feet will thank you after hours of wear. The built-in cushioned insole adds an extra layer of support, ensuring you stay comfortable from morning to night. We've also designed this shoe to be orthotic friendly, allowing you to easily insert your custom insoles for personalized arch support. Crafted with meticulous attention to detail, the Lyall boat shoe represents Rockport's commitment to quality footwear that doesn't compromise. It’s more than just a casual shoe; it’s a foundation for your daily adventures. Discover the perfect blend of timeless boat shoe aesthetics and modern comfort technology. Find your perfect fit and explore our full collection of men's casual shoes at Rockport.com.

Step into effortless style and all-day comfort with the Rockport Lance casual slip-on loafers. These versatile men's shoes are designed for the modern man who values both function and fashion. The convenient slip-on silhouette makes getting ready a breeze, perfect for busy mornings or relaxed weekends. Experience the renowned comfort Rockport is known for thanks to the integrated TruTECH technology. This innovative feature provides exceptional lightweight shock absorption with every step, reducing fatigue during extended wear. The supportive footbed cradles your feet, offering a level of ease that makes these loafers ideal for your daily routine, from running errands to casual office days. Crafted with a focus on fit, this style in a Wide width ensures a roomier, more accommodating feel. The Lance loafers are also orthotic friendly, allowing you to use your custom insoles for personalized support without compromising the sleek design. Discover the perfect blend of laid-back sophistication and engineered comfort. Refresh your footwear lineup with a pair built for real life. Explore more exceptional styles designed for movement and style at Rockport.com.

Step into all-day comfort and versatile style with the Rockport Total Motion Tilman Lace-up Casual Sneakers. Designed for the modern man who values both performance and a polished look, these sneakers provide the perfect foundation for an active lifestyle. The innovative truTECH technology delivers exceptional lightweight shock absorption, cushioning your feet from the impact of daily movement. Engineered with our signature Total Motion technology, this shoe offers enhanced support and flexibility with every step you take. The construction adapts to your natural motion, providing stability whether you're navigating a busy day or enjoying casual outings. An orthotic-friendly design allows for easy integration of your custom insoles, ensuring personalized comfort tailored to your needs. Crafted for the discerning customer at Rockport.com, the Tilman sneaker in Size 13 W combines durable materials with a contemporary lace-up silhouette. Experience the ideal blend of casual sneaker aesthetics and athletic shoe functionality. Discover why Rockport is trusted for footwear that doesn't compromise. Visit our website to explore our full collection and find your perfect fit for unmatched comfort and support.

Step into effortless style and all-day comfort with the Rockport Lyall Slip-On Boat Shoe. Designed for the modern man who values both a polished look and practical wearability, this casual shoe eliminates the need for laces with its convenient slip-on design. The almond-shaped toe provides a sleek, contemporary silhouette that pairs perfectly with chinos, jeans, or shorts. Your comfort is our priority. Each step is supported by a cushioned insole that molds to your foot, while our innovative truTECH technology delivers lightweight shock absorption to reduce fatigue. Whether you're navigating a busy day at the office or enjoying a relaxed weekend outing, these shoes provide the foundation you need. We've crafted the Lyall shoe to be orthotic-friendly, offering the flexibility to accommodate your custom insoles for personalized support. Available in a versatile Size 10 Wide, it ensures a perfect fit for those who need extra room. Discover the perfect blend of smart casual style and renowned Rockport comfort. Visit Rockport.com today to explore our full collection of men's footwear and experience why we are a leader in shoes built for real life. Elevate your everyday wardrobe with a pair that works as hard as you do.

Step into effortless style and all-day comfort with the Rockport Lyall Slip-on Boat Shoes. Designed for the modern man who values both sophistication and ease, these casual shoes offer a versatile look perfect for a variety of occasions, from weekend outings to relaxed office settings. The slip-on silhouette provides ultimate convenience, eliminating the need for laces while maintaining a secure and polished fit. Experience exceptional comfort with the built-in cushioned insole that supports your feet from morning until night. The classic almond-shaped toe adds a touch of refined style to your casual wardrobe. Rockport’s innovative truTECH® technology is at the heart of these shoes, delivering lightweight shock absorption with every step you take. This means you can stay on your feet longer without the usual fatigue, making them ideal for active days. Furthermore, this design is orthotic friendly, allowing you to use your custom insoles for personalized arch support and comfort. Discover the perfect blend of form and function. Visit Rockport.com today to explore our full collection of men’s casual shoes and find your perfect fit. Enjoy the confidence that comes with wearing footwear designed for real life, offering the durability, comfort, and style you expect from a trusted brand. Elevate your casual shoe game with the Lyall slip-ons.

Step into effortless style and all-day comfort with the Lyall Slip-on Boat Shoes from Rockport. Designed for the modern man who values both sophistication and ease, these casual shoes provide a perfect blend of classic design and innovative technology. The convenient slip-on silhouette means you can get ready and go without any fuss, making them an ideal choice for busy days. Experience superior cushioning with every step thanks to the built-in, supportive insole. The elegant almond-shaped toe offers a refined look that pairs seamlessly with chinos, jeans, or casual shorts. At the heart of these shoes is Rockport's exclusive truTECH technology, engineered to provide exceptional lightweight shock absorption. This means your feet stay comfortable and supported, reducing fatigue whether you're running errands or enjoying a weekend outing. We've crafted the Lyall boat shoe to be orthotic friendly, offering the flexibility to use your own custom insoles for personalized comfort. Available in Size 13 M, this shoe delivers a precise fit for wider appeal. Discover the perfect combination of timeless boat shoe style and groundbreaking comfort technology. Visit Rockport.com today to explore our full collection of men's casual shoes and step into a new standard of relaxed, confident footwear.

Step into effortless style and all-day comfort with the Lyall Slip-on Boat Shoe from Rockport. Designed for the modern man who values both sophistication and ease, this casual shoe offers a versatile look perfect for a variety of occasions. The convenient slip-on silhouette means you can get ready and go without any fuss, combining smart design with practical living. We’ve engineered these boat shoes with your comfort as the priority. The cushioned insole provides exceptional support from morning until night, whether you're running errands or enjoying a casual outing. The signature truTECH® technology delivers lightweight shock absorption with every step, reducing fatigue so you can stay on your feet longer in complete comfort. The classic almond-shaped toe offers a refined, polished appearance that pairs seamlessly with chinos, jeans, or shorts. Beyond its sharp look, this shoe is also orthotic friendly, allowing you to use your own custom insoles for personalized, premium support. It’s the thoughtful detail that makes Rockport footwear stand apart. Discover the perfect blend of timeless boat shoe style and innovative comfort technology. Visit Rockport.com today to explore our full collection of men's casual shoes and experience the quality craftsmanship and comfort that defines our brand. The Lyall slip-on is more than just a shoe; it's your go-to for reliable, comfortable style every day.

Step into effortless style and all-day comfort with the Lyall Slip-on Boat Shoes from Rockport. Designed for the modern man who values both sophistication and ease, these casual shoes offer a versatile look perfect for a variety of occasions. The convenient slip-on silhouette means you can get ready and go without any fuss, blending smart design with practical functionality. Experience superior comfort from the moment you put them on, thanks to the plush, cushioned insole that supports your every step. The classic almond-shaped toe provides a refined look while giving your feet ample room. At the heart of these shoes is Rockport's innovative truTECH technology, engineered to deliver exceptional lightweight shock absorption. This means you get reduced foot fatigue and enhanced energy return, whether you're navigating a busy day or enjoying a relaxed weekend. We've crafted the Lyall to be orthotic friendly, offering the flexibility to use your own custom insoles for personalized support. Discover the perfect balance of timeless boat shoe style and advanced comfort technology. Explore more premium footwear designed for your lifestyle at Rockport.com.