A date is always a reason to try harder, and for me that usually means wearing a skirt/dress. I always feel that much dressier when I have a skirt and heels on. I guess it makes me feel more womanly, and like I actually tried.
Blazer & Blouse: Anthropologie. Skirt: Forever 21. Tights: Walgreens. Shoes: Jeffery Campbell. Scarf: Flea Market. Bag: Lucky Penny. Sunglasses: Vintage. Feather Pin: Vintage (gifted).