Yes, you can wear gladiator sandals with jeans. It seems like a bizarre combination, right? The thing is, gladiator sandals are one of the most popular shoes for women in contemporary times. They can be worn with jeans, shorts and skirts and are pretty appropriate to wear at home or to work. Of course they may not be the best shoes to wear all the time because they are quite casual. That way you can wear them with jeans or shorts and feel confident wherever you go.