As the resident single person on Glamour’s shopping team, I’ve logged way too many hours figuring out what to wear on a date. This used to be a task I loathed. I’d spend so long agonizing over choosing a shirt that felt “cool without trying too hard” that I’d wind up dreading my date before it ever began.
A few years ago I realized this had to stop or I’d give up on dating altogether. So I started building a set of standardized formulas for how to style date looks, adjusting them based on the occasion’s vibe and level of intimacy. After all, what you’d wear on a coffee date is very different from what you’d slip on for dinner and dancing. If you too struggle to land on the right look, here are curated outfit ideas for what to wear on dates, organized by scenario. Steal away!
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What to wear on a first date
I don’t believe in love at first sight, but I think it’s safe to say first impressions matter. Early meet-ups, in my experience, tend to be low-key—coffee at a café, a quick drink, or a stroll. The focus of a first-date outfit should be on you, not on how trendy your shoes are. Keep things unfussy: a simple T-shirt or top in a color that brings attention to your eyes, dark-wash denim that feels subtly dressy (I’m loyal to these Agolde barrel-leg jeans), and flats you can actually walk in. A structured spring jacket—like a barn coat—pulls it together. The goal isn’t to look overly styled; it’s to feel at ease. If you’re comfortable, you’re more likely to feel confident—and that’s really what matters at this stage.
Styling tip: Jeans and flats are a perfect dressy-ish combo that puts your comfort first.