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Preston Chelsea Boots - Full-Grain Calfskin Leather Black, Beckett Simonon, $269

Bitflex Chelsea Boot - Dark Chestnut, Astorflex, $366

General Purpose Chelsea Boot - Anejo Full-Grain Leather, Thursday, $199

Soho High Heel Chelsea Boot - Black Leather, Thursday, $195

Journeyman Chelsea Boot - C.F. Stead Stone Rambler Leather, Thursday Boot Company, $325

Duke Chelsea Boot - Dark Olive Suede, Thursday Boot Company, $199

General Purpose Chelsea Boot - Vintage Tobacco Leather, Thursday Boot Company, $199

Duke Chelsea Boot - Thursday Chrome Leather Brown, Thursday Boot Company, $199

Legend Chelsea Boot - Safari Suede, Thursday Boot Company, $160

Duchess Chelsea Boot - Dark Brown Suede, Thursday Boots, $160

Reign Chelsea Boot - Full-Grain Leather/Black, Thursday Boots, $168

Knockout High Heel Chelsea Boot - Chocolate Hand-Finished Full-Grain Leather, Thursday Boots, $168