Shoes Casual & Relaxed Boots
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Nando Leather Plain Toe Chelsea Boots
Strut like you mean it in these classic leather Chelsea boots. With their pull-on ease (thanks, elastic gore!) and timeless pull-tab charm, they're ready for everything from business casual to weekend adventures. Breathable and crafted for all-day comfort, these boots are the wingman your...- $103.50
$344.99- $103.50
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Odell II Leather Wingtip Lace-up Boots
Who says rugged can't look refined? These leather lace-up brogue boots are your secret weapon for conquering the boardroom or the brewery. With a wide toe for all-day comfort and breathable materials, they're perfect for business casual or boho vibes. Add in cushioned soles,...- $36.00
$119.99- $36.00
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Old Bowen Trek Leather Side Zip Lace-up Boots
These leather combat boots are the ultimate mix of rugged vibes and casual swagger. With lace-up details and a side zipper for easy on-and-off, they're perfect for everything from boho coffee runs to stomping through fall leaves. Lugged soles mean you're ready for any...- $100.50
$334.99- $100.50
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Otis II Leather Plain Toe Chelsea Boots
These leather Chelsea boots walk the line between business-casual cool and minimalist charm. With a wide toe for all-day comfort and breathable vibes, they're perfect for conquering your to-do list or dominating fall outings. The elastic gore and pull-on style make slipping them on...- $36.00
$119.99- $36.00
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Otis II Suede Plain Toe Chelsea Boots
Slide into these suede Chelsea boots and let your style do the smooth-talking. With perforated detailing for a little extra flair and elastic gore for that effortless pull-on ease, they're the perfect mash-up of boho vibes and business casual cool. Whether you're strolling through...- $36.00
$119.99- $36.00
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Otto Leather Lace-up Plain Toe Chukka Boots
Classic meets casual cool with these wide-toe chukka boots. Perfect for when you're aiming for that "I mean business, but I'm also chill" vibe. Whether you're lacing up for a polished office look or taking them out for a crisp fall stroll, these boots...- $33.00
$109.99- $33.00
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Paul Chukka Boots
A refined take on a casual classic, these boots embody timeless style with Frye's signature craftsmanship. Made from supple leather, its minimalist, ankle-high silhouette and two-eyelet lacing offer a clean and versatile look. This comfortable lace-up boot is an effortless choice for adding sophisticated...- $57.00
$189.99- $57.00
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Paul Chukka Lite Boots
Meet the Paul Chukka. It's the kind of boot that quietly whispers, "Yeah, I've got great taste," without ever trying too hard. Clean design meets refined craftsmanship here, with premium materials, smooth leather lining, and a cushioned insole that makes every step feel like...- $60.00
$199.99- $60.00
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Paul Inside Zip Boots
Zip up. Head out. Look sharp. The Paul boot is your everyday wingman. It's rugged, refined, and ready for anything. Made from soft leather with a vintage metal zipper that's all about easy entry (no tug-of-war here), it's built for comfort and cool. The...- $69.00
$229.99- $69.00
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Paul Mid Lace Boots
Classic never looked so cool. This ankle boot is all about timeless style with a modern twist. Crafted from natural milled leather and built tough with Goodyear welt construction, it's ready for wherever the day takes you. The round toe and traction-ready rubber outsole...- $69.00
$229.99- $69.00
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Pebbled Leather Chukka Boots
These Joseph Abboud leather chukkas bring understated style to everyday dressing. Crafted with a subtle pebbled texture, they offer visual depth while maintaining a refined, polished look. The classic lace-up design and cushioned sole provide comfort and versatility making them an easy match with...- $36.00
$119.99- $36.00
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Protege Leather Lace-Up Cap Toe Boot
Meet your go-to boots for that perfect blend of rugged charm and boho vibes. These leather lace-ups don't just look good - they breathe easy, keeping your feet comfy from coffee runs to casual nights out. Built for the stylish wanderer who loves a...- $105.00
$349.99- $105.00
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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 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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Seneca Leather Moc Toe Lace-Up Chukka Boots
These boots don't just walk the walk - they stroll, saunter, and strut. Crafted in smooth leather with stitching that winks at your style game, they're the minimalist's dream with just the right amount of flair. Lace them up for business casual finesse or...- $36.00
$119.99- $36.00
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Stone Plain Toe Boots
Cold weather, meet your new style sidekick. The Stone Boot is made for making an entrance, whether you're strolling city streets or heading out on a crisp winter adventure. Wrapped in a genuine suede upper, this boot delivers rich texture, while the softly trimmed...- $38.70
$128.99- $38.70
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Thomas Cap Toe Boots
Built for comfort. Ready for anything. These Dockers boots are your feet's new best friend. With the Supreme Comfort EVA footbed, every step feels like a soft, supportive hug. Add in a moisture-wicking sock cover, and you've got dry, happy feet from sunup to...- $28.50
$94.99- $28.50
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Townsend Plain Toe Chelsea Boots
Sharp and streamlined, these Stacy Adams boots offer timeless appeal with a modern edge. Elastic side panels and a pull-on design make them easy to wear, while a cushioned insole and lightweight outsole keep you comfortable on your feet. Crafted with a smooth leather...- $45.00
$149.99- $45.00
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Traveler Plain Toe Chukka Boots
Polished yet practical, these Florsheim chukka boots deliver everyday versatility with a refined edge. Crafted from rich leather and set on a durable rubber sole, it pairs classic chukka styling with modern comfort features. A cushioned footbed and soft Suedetec lining provide support from...- $40.50
$134.99- $40.50
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Truman Plain Toe Chelsea Boots
Rugged charm meets all-day comfort. These boots from Dockers are built for wherever the day takes you; from city streets to weekend trails. With a Supreme Comfort EVA footbed and massaging textures, your feet stay supported and relaxed, while the moisture-wicking sock cover keeps...- $28.50
$94.99- $28.50
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