I've been turning night out apparel in to office appropriate wear for years (who wants to spend mucho $$$ on corporate clothes...yick). Take a high waisted pencil skirt from day to night by swapping out a sweet bow blouse for a fitted, cropped turtleneck top and add an ornate cuff and gemstone studded belt for unique pops of pow.
Dree Hemingway epitomizes fresh, interesting, downtown NYC style by incorporating unique pieces in to her wardrobe, like paneled leather jeans, multi-textured baseball/bomber style jackets, and pieces of jewelry with a bohemian flair.
Make a girly pumpkin by glueing on some false lashes and using a lips shaped pin for the mouth. Create a street style cool pumpkin by using a liquid adhesive and different sized gold studs (or just push the prongs of a stud right in to your pumpkin).