Being able to ride your bicycle while maintaining a fashion style isn't all that important, but nonetheless still very impressive. Especially if the attire isn't bicycle friendly, comfortable or convenient. There's nothing wrong with riding in jeans, spandex, or a pair of shorts, but style credit must be given for people that ride in dresses, skirts, or suits.
One of my favorite blogs is Cycle Chic, which photo documents fashion mixed with bicycles in Copenhagen. Pueblo may not be quite there, but this is a start.