Chelsea Boots for Men Add to WardrobeRemove from Wardrobe FavoriteUnfavorite Shop It Outfits Sort by featured Sort by price: high to lowSort by price: low to high Flexi Gasly Chelsea Boot $104 Church's Chelsea Ankle Boots $560 $1,120 Church's Welwyn Chelsea Boots $672 $1,120 Dr. Martens Vegan 2976 Chelsea Boots $210 $234 Fratelli Rossetti Ankle Length Leather Boots $453 $647 Fratelli Rossetti Ankle Length Suede Boots $332 $415 Jil Sander Leather Ankle Boots $1,050 Juun.J Ridged Sole Leather Boots $624 $832 Tommy Hilfiger Ankle Chelsea Boots $182 $192 Common Projects Leather Chelsea Boots $670 Bottega Veneta Puddle Knee High Boots $750 Rick Owens Lug Sole Ankle Boots $1,350