I’ve got a few pairs of DeFeet wool socks and really rate them. The Wooleator is thin, so fits inside summer shoes, and is very versatile for year round use. Very few socks will keep you warm in ventilated summer shoes that are designed for air flow, so I add neoprene toe covers or knitted over socks as required. I rarely use overshoes, because by the time I need those I’m more likely to be wearing winter boots. Those are a size larger than usual and I fill the space with DeFeet Woolie Boolie socks. The DeFeet socks are available in different cuff heights and I always go for the longest available, as any sort of gap around the ankles is no good. Silk liner socks are super thin and can add an extra layer if it’s very very cold.