Shoes Casual & Relaxed
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Redwood Edge Moc Toe Chukka Boot
Due to vendor restrictions, we can only ship Timberland products to the 50 states with the U.S. and APO or FPO addresses.Think of these Timberland Redwood Edge chukka boots as the perfect handshake between rugged capability and office-ready style. They feature premium leather that...- $45.00
$149.99- $45.00
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Redwood Edge Moc Toe Oxford
Due to vendor restrictions, we can only ship Timberland products to the 50 states with the U.S. and APO or FPO addresses.Meet the Timberland Redwood Edge Moc Toe Oxford -- the shoe that treats your feet like royalty while keeping things strictly business on...- $39.00
$129.99- $39.00
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Redwood Falls Moc Toe Waterproof Boot
Due to vendor restrictions, we can only ship Timberland products to the 50 states with the U.S. and APO or FPO addresses.These genuine leather slip-on loafers are classic with a twistthink Eclectic Grandpa meets Polished Prep. Designed for business casual days or spontaneous coffee...- $48.00
$159.99- $48.00
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Reece Casual Slip-On Shoes
Effortless comfort meets modern design in this casual slip-on. Featuring Step Activated technology, it allows for hands-free on and off, making it ideal for those on the go. The water-resistant leather upper ensures durability, while the truTECH cushioning system provides lightweight shock absorption for...- $40.50
$134.99- $40.50
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Remi Leather Cap Toe Oxfords
Your 9-to-5 just got an upgrade. These leather lace-up Oxfords bring minimalist vibes with maximum impact. Perfect for the boardroom or a dinner date, these classic medallion cap-top shoes are sleek, polished, and ready to work as hard as you do. Pair them with...- $40.50
$134.99- $40.50
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Remi Leather Plain Toe Lace-Up Oxfords
Your 9-to-5 just met its new best friend. These leather plain toe Oxford shoes are the ultimate wingman for the boardroom and beyond. With fully cushioned insoles that whisper "comfort" and a minimalist lace-up design that screams "effortless style," they're perfect for work or...- $40.50
$134.99- $40.50
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Remi Moc Toe Slip On Shoes
These moc toe slip-on shoes from Florsheim have a clean, elegant design that perfectly complements any dress or casual style. Crafted with genuine leather uppers, they also feature fully cushioned footbeds for all-day comfort.- $40.50
$134.99- $40.50
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Remi Penny Loafer
Refresh your daily look with the sophisticated style of these classic penny loafers. This pair features full leather uppers with a rich burnished finish and soft suede for a refined appearance that looks great with your favorite trousers. The fully cushioned footbed and flexible...- $40.50
$134.99- $40.50
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Reuben Moc Toe Loafers
These loafers offer a refined yet relaxed look with versatile styling. A sleek leather upper and a moc toe design give a nod to timeless sophistication. The cushioned footbed and soft synthetic lining ensure comfort throughout the day, while the slip-on style adds convenience...- $60.00
$199.99- $60.00
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Richardson Moc Toe Bit Slip-On Shoes
Refined yet relaxed, the Stacy Adams Richardson blends timeless loafer styling with contemporary comfort. A bit detail adds polish, while soft microfiber linings and a fully cushioned footbed deliver all-day wearability. Finished with a flexible, lightweight sole, it's an easy choice for workdays or...- $27.00
$89.99- $27.00
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Richmont Moc Toe Bit Loafers
Here's a shoe that knows how to make an entrance without saying a word. Richmont's moc toe and polished bit detail bring that extra something to your outfit, while the easy slip-on style keeps things effortless. Inside, it's all about comfort. Microfiber linings wrap...- $27.00
$89.99- $27.00
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Rico Formal Velvet Lace-Up Sneakers
Step up your style game with these Belvedere Velvet Lace-Up Sneakers. Equal parts sophisticated and effortless, they pair formal velvet vibes with a laid-back silhouette. Perfect for date nights or jazzing up your everyday look, these sneakers are all about that quiet luxury. With...- $30.00
$99.99- $30.00
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Ridgely Moc Toe Loafers
Why settle for ordinary when you can have serious style and all-day comfort? The Ridgely is crafted from smooth leather for a polished look, but it's what's inside that makes it a game-changer. Leather lining keeps things breathable, while the RedZone removable footbed with...- $27.00
$89.99- $27.00
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Ripley Embellished Smoking Loafers
When sharp meets suave, the Ripley Embellished Smoking Loafers step in. Designed for black-tie nights and luxe vibes, these loafers flaunt a sleek high-vamp silhouette and chic metal detailing. Slip-on style? Check. Cushioned insole? Oh, yes. They're not just shoes, theyre your all-access pass...- $24.00
$79.99- $24.00
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Ripley Wingtip Lace-Up Oxford
Find the perfect balance of heritage character and refined style with a classic shoe that bridges the gap between casual weekends and smart dress codes. This premium Johnston & Murphy oxford features a rich suede upper detailed with timeless wingtip patterning, creating a textured...- $54.00
$179.99- $54.00
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Rodger Casual Loafers
This Rockport loafer blends timeless style with modern comfort, designed for those who are always on the go. Seamlessly transitioning from busy workdays to relaxed weekends, this easy slip‑on features a grippy pieced rubber outsole and advanced cushioning that feels so comfortable you might...- $37.50
$124.99- $37.50
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Rolan Leather Boys Cap Toe Dress Shoes
When your little gentleman steps into these lace-up Oxford dress shoes, he'll feel like a big deal (and look like one too). Perfect for formal occasions or just leveling up his everyday style, these classics combine breathable leather with a cushioned toe for all-day...- $18.00
$59.99- $18.00
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Rolinde Slip-On Casual Slides
These Rolinde slide sandals from Calvin Klein add a sophisticated touch to your warm-weather rotation. Designed for effortless wear, these sandals feature a round open toe and an easy slip-on construction with double strap detailing on the upper. The faux leather straps are complemented...- $21.00
$69.99- $21.00
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Roose Sandals
Undeniably versatile, these open-toe casual sandals are designed for effortless everyday wear. The minimalist silhouette features wide, comfortable straps for a secure fit, while the lightweight construction ensures all-day ease. Crafted with a durable synthetic upper, lining, and sole, they offer a perfect balance...- $17.70
$58.99- $17.70
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Roseto Luxe Leather Plain Toe Oxfords
Step into sophistication with these Luxe Roseto Leather Plain Toe Derby Oxfords. Crafted from polished black leather, theyre a perfect fusion of timeless style and everyday functionality. Featuring a sleek almond toe, lace-up closure, and comfortable rubber sole, they'll be your go-to for everything...- $42.00
$139.99- $42.00
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