Leather 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 Prada Square Toe Chelsea Boots $1,320 Free US Shipping! Saint Laurent Vassili 60mm Ankle Boots $1,190 Free US Shipping! Guidi Square Toe Leather Boots $1,756 Free US Shipping! Ferragamo Buckled Chelsea Boots $903 $1,290 Free US Shipping! Balenciaga Excavator Curved Toe Boots $995 Free US Shipping! Mou Stitch Detail Ankle Boots $338 Free US Shipping! Prada Turn Up Toe Leather Ankle Boots $1,790 Free US Shipping! Santoni Contrast Panel Chelsea Boots $820 Free US Shipping! Moma Calf Leather Ankle Boots $288 $411 Free US Shipping! Tom Ford Side Zip 50mm Ankle Boots $2,462 Free US Shipping! Thom Browne Stripe Trim Ankle Boots $420 Free US Shipping! Tommy Hilfiger Rounded Chelsea Booties $152 $221 Free US Shipping!