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21+ Chelsea Boots With Jeans Pics . Options abound for wearing jeans with your chelsea boots! Chelsea boots come in a variety of colors and materials. Brown Boots Outfit for Men-30 Ways to wear Brown Boots from www.outfittrends.com Although you can probably pull off many shoes loose around your ankle, chelsea 4. You can pair them with distressed jeans for a casual look, or dark wash jeans for a more formal occasion. The chelsea boot's original design traces back to the 1850's. Easy to throw on after work for drinks or dinner, a pair of these boots in a dark brown or black will instantly elevate a pair of indigo jeans and a casual shirt. So you should try to approximate the same vibe with. Easy to throw on after work for drinks or dinner, a pair of these boots in a dark brown or black will instantly elevate a pair of indigo jeans and a casual shirt. I'd prefer some knee r...