Got a party coming up and want to nail that old money aesthetic? Whether it's a cocktail party, rooftop drinks, a black-tie event, or just a fancy night out, these 20 outfit ideas will have you looking polished, classy, and effortlessly put together. A sleek dress, an elegant skirt with heels, or a tailored evening look—whatever your vibe, it’s all about timeless style that doesn’t try too hard.