You know the night we’re talking about. After months of sticky, sweaty evenings, you step outside and finally there’s a little chill in the air. Not enough for a proper coat, but just cool enough to remind you how much better getting dressed can be in the fall. Suddenly, layers are an option again. Pants aren’t a punishment. And that lightweight jacket or overshirt you bought weeks ago can finally leave the closet.

For the first genuinely cool night of the season, don’t overdo it. Start with a textured knit polo or lightweight sweater, add relaxed trousers or dark denim and throw on a light outerwear option like Buck Mason’s felted field shirt. Then ground everything with something more substantial underfoot: Paraboot’s legendary Michael derby offers plenty of comfort while still looking sharp. It’s just enough fall to scratch the itch, because heavier layers will have plenty of time to come.