According to Country Outfitter, dresses that look good worn with cowboy boots include simple sundresses, floral print dresses and dresses made of denim, lace or eyelet. The best dress length for wear with cowboy boots is right above the knee.
Belt a simple dress with a leather belt that complements the cowboy boots to draw attention to them. Because cowboy boots make such a strong fashion statement when worn with a dress, keep the dress itself simple, and don't overaccessorize. Avoid wearing additional cowboy accessories, such as a large cowboy hat, to ensure the boots stand out. Cowboy boots also work well in the winter when worn with sweater dresses or over heavy leggings.