What does "Dressy Casual" Mean? Nov 6, 2011 0:53:20 GMT -5 Quote Select PostDeselect PostLink to PostMemberGive GiftBack to Top Post by sexiest on Nov 6, 2011 0:53:20 GMT -5 Possibly the safest way to dress appropriately is to avoid certain things. Even though some people might consider fancy jeans as dressy casual, others don’t. Therefore, avoiding jeans is a good idea.