So you have a date. You old dog, you-congratulations! Figured out where you’re going and what you’re doing? Now comes the hard part: what to wear. Date night outfits, whether you’ve made a coveted Saturday night reservation or are planning a casual night out, are pretty simple: They’ll help you look your best without looking like you’ve tried too hard.
If you’re on the starting line of courtship, aim to appear cool and put-together, but still likable. You. Comfortable, well-fitting basics that don’t scream work best. Win them over with your personality and your jokes, not the big logo on your sweater. The main thing, even during these sweaty months, is to look like you’ve put in some real effort without expecting your clothes to do the hard work for you. And, yes, the old adage holds true: People really do look at your shoes first, so make sure you’re not wearing anything completely caked on. Even on hot summer days, a backup layer is always smart, even if things transition from dinner to a stroll or dinner out.
This isn’t just wise advice for beginners. If you’ve been with your partner for a while, it’s worth keeping things interesting. Dressing up a bit for a night out shows that you still care—trust me, they’ll appreciate it. To inspire you, we’ve put together five date night outfits for every type of scenario you might encounter, and explained how to dial it in for each. Good luck out there, stud.
6 Key Elements for a Great Date Night Outfit
Link-up at a leisurely day
Daytime holiday dates are the most casual. It’s a simple temperature check, but that doesn’t mean you can sweat it out. Maybe it’s coffee, maybe it’s going for a walk, but it’s summer, you’re wearing a light sweater, you’re basically Billy Crystal when harry met sally. The goal is to appear effortlessly put together—to show them that you’ve got your life in order. (Bonus points if you bring a dog, ideally your own.) Here, some ways to make an impact: a bright knitwear, some rugged jeans, and a strong, pretty belt and watch to tie it all together. If they like the fit – and you don’t say anything stupid – you may just earn yourself a date upgrade for drinks or dinner.
