Colored pants make a statement. Dress up your jeans to make a statement. A lightweight maxi dress with a layered necklace would do the trick. With chambray, you can. What do you wear to a dinner date at your house? This date night can be dressed up or down. Wear your finest dress and heels, or go casual with jeans and a sweater. Get ready, this 20th wedding anniversary dinner is as romantic as they come! Katherine had the sweet idea to. Wear a pair of your favorite sandals or white gym shoes.