I always find myself envying the woman who shows up to a party underdressed. To me, it signals confidence: she wears what she wants, what feels comfortable and authentic, rather than conform to a dress code. However, in order for the outlier outfit to pass muster in my book, it needs to be elegant and considered, glazed with festive formality. In short, there's an art to underdressing, and it's one I want to master. I'm deriving inspiration from the look, above, a winning mix of polished denim, glistening patent leather, sheer tights (I have these socks!), and sumptuous satin (on sale here), along with Leandra Cohen's sequins and leather, below. (Shop here and here.) Some of my favorite pieces invited to the party: this striking Cult Gaia metallic top, this Marissa Webb blazer vest, and this embellished Toteme sweater.

Photos: Symphony of Silk, Leandra Cohen