I’ve worn shorts everyday since September 2012. Yeah, I haven’t worn long pants since then, just shorts above the knees no matter the weather we have in the northwest. I’ve learned to wear various lengths of socks based on the weather, namely the temperature, but also the wind and rain or occasional snow. That means I have a huge drawer full of knee socks, over the knee (OTK) socks, and yes, thigh high socks.
The knee high socks are worn when the temperature drops below 50 or above that if it’s windy or raining. Above that, it’s just regular ankle socks, which is from about May into October, where fall weather changes back to knee socks. The OTK socks are worn when the temperature drops below 40 and the knees demands knee sweaters.
I use a product called Body Adhesive to hold the socks up, It’s never failed, even in the worst weather. The higher socks are for temperature near or below freezing to keep the thighs warm. Not surprisingly most of the socks I buy are labelled women’s socks, but in reality socks don’t care the gender of the feet they’re on, only that they fit and keep the person warm with style.
I also had Gore-Tex rain pants cut off into shorts slightly longer than the shorts to keep the shorts dry, so both are above the knees. I hate longer shorts and have all the shorts altered to be 1″ to 3″ above the knee depending on the weather. I also have a few pair of gaters for snowy or very rainy weather. They work better than long pants every could and why I’ll keep wearing shorts.
What I’ve learned from 4 winters in shorts is that if you’re walking your legs don’t really get cold, unless there’s a strong wind, but then most good wool or thck cotton socks do well against the wind, And the legs don’t get wet since you’re moving, and only from the water from the shoes or occasional mud puddle you don’t see.
It’s interesting now that I don’t have any long pants which fit anymore. Having walked over 4,200 miles I’ve lost 45+ pounds in the same period, so none of my old jeans fit. Even some of the shorts are getting baggy, but a smaller size is too small. I’m between a small and a medium now. All that said, I like wearing shorts everyday, and don’t plan to change, and the weather surely isn’t going to change that or me.