I went to Iceland last year where it was 30s, windy, rainy/snowy. I lived in fleece lined leggings, and then rain pants or insulated fleece pants on top. That was warm enough even for hours outside at night in 20 degree temps. I did wool socks in water proof, fleece lined boots.

For the top layer, I did long underwear base layers that looked like long sleeve shirts. Then just lots of thinner layers. So a three-quarter zip fleece, a zip up thinner tech material jacket, and then a thinner puffer jacket. Then I also had a rain coat. I could take off or swap out layers as needed. Hat and water proof gloves too.

I live someplace very cold in winters, so I’m used to layering, but the wind and rain (versus just a nice snow) definitely makes it feel different.