We may earn money or products from the companies mentioned in this post.
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Ben Sherman Stitch Out Chukka Boot
$165$99 -
Millburn Co. Roper-Toe Chelsea Boot
$169$129 -
Vintage Shoe Company Adrian Leather Chukka Boot
$260$129 -
Millburn Co. Fur Hiker Boot
$169$129 -
Millburn Co. Collared Leather Boot
$175$129 -
Gordon Rush Alpine Ankle Boot
$375$129 -
Eastland Barron Boot
$130$95 -
Millburn Co. Wingtip Broguing Ankle Boot
$169$129 -
Eastland Canton Limited Edition Chukka Boot
$200$89 -
McCarren & Sons Wingtip Leather Boot
$199$129 -
Eastland Lumber Up Limited Edition Hi Top Boot
$250$109 -
Russell Park Sahara Crepe Chukka Boot
$149$99 -
Russell Park Sahara Leather Chelsea Boot
$149$99 -
Millburn Co. Wingtip Waxed Suede Ankle Boot
$199$129 -
Warfield & Grand Leather Chukka Boot
$215$99 -
Millburn Co. Leather Chukka Boot
$175$129 -
Ben Sherman Gabe Chukka Boot
$165$89 -
McCarren & Sons Leather Chukka Boot
$209$129 -
Ben Sherman Brent Ankle Boot
$170$99 -
Original Penguin Jerry Jeff Boot
$185$99 -
Gordon Rush Wingtip Brogue Boot
$315$129 -
Original Penguin Padded Hiker Boot
$185$99 -
Eastland Lumber Up Boot
$125$89 -
McCarren & Sons Leather Lace-Up Boot
$209$129 -
Ben Sherman Leon Distressed Mid-Top Boot
$170$99 -
Eastland Barron Limited Edition High-Top Boot
$250$85 -
Eastland Seneca Chukka Boot
$110$79 -
Eastland High Fidelity Hi Top Boot
$200$99 -
Vintage Shoe Company Adrian Suede Chukka Boot
$270$129 -
Original Penguin Merle Chukka Boot
$175$99 -
Russell Park Gomma Wingtip Suede Boot
$149$99 -
Marc New York by Andrew Marc Stanton Canvas Chukka Boot
$128$65 -
Marc New York by Andrew Marc Harman Suede Chukka Boot
$148$75 -
Native Fitzroy Boot
$110$45 -
Native Fitzroy Boot
$110$45 -
Wall + Water Top Stitch Chukka Boot
$249$129 -
Giorgio Brutini Munro Monkstrap Boot
$100$69 -
Giorgio Brutini Cuban Heel Leather Boot
$90$65 -
Modern Fiction Wingtip Boot
$325$124.99 -
Ben Sherman Alejandro Lug Chukka Boot
$165$99 -
Ben Sherman Alejandro Lug Chukka Boot
$165$89 -
Russell Park Gomma Wingtip Leather Boot
$149$99 -
Russell Park Gomma Wingtip Suede Boot
$149$99 -
Russell Park Sahara Leather Boot
$149$99 -
Millburn Co. Roper-Toe Chukka Boot
$169$129 -
Millburn Co. Wingtip Ankle Boot
$175$129 -
Eastland Lumber Up Boot
$250$95 -
Eastland Barron Limited Edition Boot
$250$85 -
Eastland Seneca Chukka Boot
$110$79 -
Eastland Daily Double Chelsea Boot
$115$85 -
Russell Park Sahara Leather Boot
$149$99 -
Modern Fiction Wingtip Boot
$330$124.99 -
Gordon Rush Leather Chelsea Boot
$330$125 -
Ben Sherman Gabe Chelsea Boot
$165$99 -
Vintage Shoe Company Carlyle Suede Hi Top Boot
$315$129 -
Vintage Shoe Company Clay Leather Boot
$345$128.99 -
WOLVERINE 1883 Driscoll Moc-Toe Boot
$225$125 -
McCarren & Sons Lace-Up Leather Boot
$199$129 -
Eastland Lumber Up Shearling Lined Boot
$130$95 -
Rush by Gordon Rush Lace-Up Chukka Boot
$195$115 -
Russell Park Moc Toe Leather Boot
$149$99 -
WOLVERINE 1883 Driscoll Moc-Toe Boot
$225$125 -
Original Penguin Grappler Boot
$185$99 -
WOLVERINE 1883 Hensel Chukka Boot
$195$99 -
Timberland Wodehouse Leather Ankle Boot
$300$129 -
Marc New York by Andrew Marc Lexington Leather Chukka Boot
$148$89 -
Marc New York by Andrew Marc Essex Chukka Boot
$148$89 -
Marc New York by Andrew Marc Essex Lace-Up Chukka Boot
$148$89 -
Andrew Marc Haven Chukka Boot
$178$79 -
McCarren & Sons Leather Chelsea Boot
$209$129 -
Andrew Marc Haven Chukka Boot
$178$79 -
Marc New York by Andrew Marc Harman Suede Chukka Boot
$128$79 -
Timberland Wodehouse Leather Ankle Boot
$300$129 -
Timberland Wodehouse Leather Ankle Boot
$300$129 -
McCarren & Sons Lace-Up Leather Boot
$199$129 -
SWIMS Barry Hi Top Waterproof Boot
$235$128.99 -
Native Jimmy 2.0 Winter Boot
$120$49 -
Rush by Gordon Rush Roper-Toe Chelsea Boot
$245$115 -
Marco Vittorio Leather Chelsea Boot
$260$115 -
Andrew Marc Norwood Leather Boot
$248$129 -
Andrew Marc Dorchester Chukka Boot
$178$89 -
Marc New York by Andrew Marc Howard Suede Chukka Boot
$148$89 -
Andrew Marc Haven Chukka Boot
$178$79 -
McCarren & Sons Leather Boot
$199$129 -
Marc New York by Andrew Marc Harman Suede Chukka Boot
$148$89 -
Andrew Marc Dorchester Suede Chukka Boot
$178$89 -
Original Penguin Roper-Toe Hiker Boot
$185$34.99 -
Tretorn Strala Solid Ankle Rain Boot
$75$45 -
Rush by Gordon Rush Roper-Toe Chelsea Boot
$245$115 -
Ben Sherman Gabe Chelsea Boot
$165$99 -
Marc New York by Andrew Marc Harman Suede Chukka Boot
$128$89 -
Original Penguin Merle Leather Chukka Boot
$175$34.99 -
John Varvatos Star USA Bonham Leather Boot
$398$129 -
Ben Sherman Aberdeen Gore Chukka Boot
$160$69 -
Nisolo Chavito Chukka Boot
$148$99 -
Campobello Lace-Up Chukka Boot
$225$88.99 -
Warfield & Grand Wingtip Leather Boot
$235$105 -
Campobello Wingtip Chelsea Boot
$295$129 -
McCarren & Sons Wingtip Leather Boot
$209$129 -
McCarren & Sons Leather Wingtip Boot
$199$98.99 -
Timberland Camp 73 Chukka Boot
$140$69 -
John Varvatos Star USA Star Chukka Boot
$228$125 -
Timberland Moc Toe Leather Boot
$140$69 -
Timberland Newmarket Leather Boot
$140$79 -
Andrew Marc Eugene Chelsea Boot
$198$89