I typically wear T-shirts and Hawaiian shirts in the summer, underneath a black hoodie. In the winter, one of my scarves and a knit hat, and an old beat-up leather bomber jacket passed down from a parent, which is one of the most comfortable things I have ever worn in my life. That is on top of the hoodie, by the way.
I rarely take my hoodie off, and have only been hoodie-less for lack of having a hoodie the past couple years.
Blue cargo jeans. Always. so many pockets, so much comfort. Black all-around shoes and, on special occasions, I wear my plain old straw fedora, which has gotten a bit worn over the years, but still is my favorite head-topping apparatus.
if it's a really cold special occasion, I get the enjoyment of wearing my Fourth Doctor scarf and my Fedora at the same time. It feels awesome.