There are a few things that you should probably have in your closet at all times. Whether you wear hooded sweatshirts often or not, I would recommend not, they are pretty good to have. It's a very casual item that can keep you warm, help layer or be worn to the corner store in you PJs. This might seem obvious but I'm not just recommending your Russel Athletics sweater. It would be a good idea to have at least one well made, well fitted, nice plain colored hoody. Some of the best options I've seen are this version by Rittenhouse, APC's last winter or by Wings+Horns. The simplicity of a cotton sweater is functional and if you have the right one you'll feel comfortable wearing it anywhere - just don't wear it everywhere.