Somehow the phrase “going-out outfit” still conjures the college-era formula of jeans, a tiny top, and heels, even though I hadn't dressed that way in years. Is this an actual outfit night, or just good jeans and a jacket? Sometimes your clothes don't fit the way they used to, or they do—but they still don't feel like the right answer. If your body has changed, the going-out pieces you once reached for probably no longer feel quite right. They're often what make an outfit feel like it belongs in 2026 rather than 2016.