Autumn is prime dating season. We don’t make the rules. But there’s something romantic in the air when things turn crisp in the evening, right? It makes getting dressed feel a little more exciting. Maybe it’s the prospect of a cozy, candlelit restaurant or the excuse to linger over another drink before heading back out into the chilly night. Whatever the plans, the season offers a welcome opportunity to put a little more thought into your outfit. You can finally play with layers, richer colors and interesting textures—all the things that make an outfit feel more stylish. And when you’re trying to make a good impression, that’s never a bad thing.

The key is looking like you made an effort without appearing to have tried too hard. Start with a dark jacket over a fine-gauge knit, something soft and inviting rather than stiff or overly formal. Add relaxed tailored trousers and a pair of loafers or maybe some boots to give the look some weight. A handsome hand-wound watch and a good fragrance finish things off. It’s confident and just dressed-up enough to suggest that tonight might turn into something worth remembering.