Discover our Men’s Heritage Leather Boots Collection – up to 80% off timeless designs that combine rugged craftsmanship with effortless style.

Each pair is produced in limited quantities, making it your reliable companion for any occasion. If you find a style you love, act fast — once it’s gone, it’s gone for good.

10% EXTRA ON 2 ITEMS
15% EXTRA ON 3 ITEMS
20% EXTRA ON 4 ITEMS
25% EXTRA ON 5+ ITEMS

No code needed – the discount is automatically applied at checkout.

35 products

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Dawson™ | Classic Oxford BootsDawson™ | Classic Oxford Boots
Dawson™ | Classic Oxford Boots Sale price$79.95 USD Regular price$160.00 USD
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Winston - Oxford Classic shoesWinston - Oxford Classic shoes
Winston - Oxford Classic shoes Sale price$74.95 USD Regular price$150.00 USD
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Marcel™ | Classic Oxford ShoesMarcel™ | Classic Oxford Shoes
Marcel™ | Classic Oxford Shoes Sale price$74.95 USD Regular price$150.00 USD
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James Men's Genuine Leather Shoes with High-Quality FinishJames Men's Genuine Leather Shoes with High-Quality Finish
James Men's Genuine Leather Shoes with High-Quality Finish Sale price$74.95 USD Regular price$150.00 USD
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Jason™ | Vintage Style shoesJason™ | Vintage Style shoes
Jason™ | Vintage Style shoes Sale price$74.95 USD Regular price$150.00 USD
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Hunter™ | Men's Vintage BootsHunter™ | Men's Vintage Boots
Hunter™ | Men's Vintage Boots Sale price$74.95 USD Regular price$150.00 USD
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Bradford™ | Hiking shoesBradford™ | Hiking shoes
Bradford™ | Hiking shoes Sale price$69.95 USD Regular price$140.00 USD
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Darell™ | Double Monk Strap BootsDarell™ | Double Monk Strap Boots
Darell™ | Double Monk Strap Boots Sale price$94.95 USD Regular price$190.00 USD
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Peyton | Chique Ankle BootsPeyton | Chique Ankle Boots
Peyton | Chique Ankle Boots Sale price$94.95 USD Regular price$190.00 USD
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Devin - Waterproof Non Slip Vintage BootsDevin - Waterproof Non Slip Vintage Boots
Devin - Waterproof Non Slip Vintage Boots Sale price$94.95 USD Regular price$190.00 USD
Color
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Onyx™ | Bossy-style Men's BootsOnyx™ | Bossy-style Men's Boots
Onyx™ | Bossy-style Men's Boots Sale price$94.95 USD Regular price$190.00 USD
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Bertolini Oxford ShoesBertolini Oxford Shoes
Bertolini Oxford Shoes Sale price$94.95 USD Regular price$190.00 USD
Color
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Mike™ | Elegant Office ShoesMike™ | Elegant Office Shoes
Mike™ | Elegant Office Shoes Sale price$39.95 USD Regular price$80.00 USD
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Spencer™ – Orthopedic Slippers for MenSpencer™ – Orthopedic Slippers for Men
Spencer™ – Orthopedic Slippers for Men Sale price$39.95 USD Regular price$80.00 USD
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Samuel Thatcher Dress BootsSamuel Thatcher Dress Boots
Samuel Thatcher Dress Boots Sale price$99.95 USD Regular price$200.00 USD
Color
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Marshall™ Men's Orthopedic ShoesMarshall™ Men's Orthopedic Shoes
Marshall™ Men's Orthopedic Shoes Sale price$94.95 USD Regular price$190.00 USD
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Chris™ | Orthopedic Leather Men's SandalsChris™ | Orthopedic Leather Men's Sandals
Chris™ | Orthopedic Leather Men's Sandals Sale price$79.95 USD Regular price$160.00 USD
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Dallas | Timeless Chukka BootsDallas | Timeless Chukka Boots
Dallas | Timeless Chukka Boots Sale price$79.95 USD Regular price$160.00 USD
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Alexander Prescott Dress ShoesAlexander Prescott Dress Shoes
Alexander Prescott Dress Shoes Sale price$79.95 USD Regular price$160.00 USD
Color
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Marshall™ Men's Orthopedic ShoesMarshall™ Men's Orthopedic Shoes
Marshall™ Men's Orthopedic Shoes Sale price$69.95 USD Regular price$350.00 USD
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Massimo™ | Stylish Slip-On ShoesMassimo™ | Stylish Slip-On Shoes
Massimo™ | Stylish Slip-On Shoes Sale price$69.95 USD Regular price$350.00 USD
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Torricelli SneakersTorricelli Sneakers
Torricelli Sneakers Sale price$69.95 USD Regular price$350.00 USD
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Aaron™ | Vintage Men's BootsAaron™ | Vintage Men's Boots
Aaron™ | Vintage Men's Boots Sale price$69.95 USD Regular price$350.00 USD
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Giovanni™ | Boss-style Classic ShoesGiovanni™ | Boss-style Classic Shoes
Giovanni™ | Boss-style Classic Shoes Sale price$74.95 USD Regular price$150.00 USD
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Oxford Royal BrogueOxford Royal Brogue
Oxford Royal Brogue Sale price$74.95 USD Regular price$150.00 USD
Color
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Wayne™ | Timeless Chelsea BootsWayne™ | Timeless Chelsea Boots
Wayne™ | Timeless Chelsea Boots Sale price$74.95 USD Regular price$150.00 USD
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Vincent | Chelsea bootsVincent | Chelsea boots
Vincent | Chelsea boots Sale price$74.95 USD Regular price$150.00 USD
Color
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Oliver Ashford Oxford BootsOliver Ashford Oxford Boots
Oliver Ashford Oxford Boots Sale price$74.95 USD Regular price$150.00 USD
Color
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Vincenzo - Timeless sneakersVincenzo - Timeless sneakers
Vincenzo - Timeless sneakers Sale price$74.95 USD Regular price$150.00 USD
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Owens | Chelsea bootsOwens | Chelsea boots
Owens | Chelsea boots Sale price$74.95 USD Regular price$150.00 USD
Color
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Ashford Dress ShoesAshford Dress Shoes
Ashford Dress Shoes Sale price$74.95 USD Regular price$150.00 USD
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Terence™ - Handcrafted Orthopedic ShoesTerence™ - Handcrafted Orthopedic Shoes
Terence™ - Handcrafted Orthopedic Shoes Sale price$74.95 USD Regular price$150.00 USD
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Oxford Ridge Leather SneakersOxford Ridge Leather Sneakers
Oxford Ridge Leather Sneakers Sale price$74.95 USD Regular price$150.00 USD
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Quinn – All-day shoesQuinn – All-day shoes
Quinn – All-day shoes Sale price$74.95 USD Regular price$150.00 USD
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Gerald Wentworth Chelsea BootsGerald Wentworth Chelsea Boots
Gerald Wentworth Chelsea Boots Sale price$74.95 USD Regular price$150.00 USD
Color

FREE SHIPPING

Enjoy free shipping across the U.S. on us, today only! Find something you love, and we will cover the shipping. Every order ships free, straight to your door.

LOVED FOR THE COMFORT

Timeless comfort, made to move with you Feel relaxed, confident, and beautifully at ease in every piece.

30-DAY MONEY BACK GUARANTEE

At Olivia & Heather Boutique, we believe in your satisfaction. Enjoy our 30-day return policy for peace of mind!