Q: I love the idea of wearing hats as a way to be more stylish, but in what circumstances are they appropriate?
A: Fedoras, floppy hats and even toboggans are fun to wear, especially on dirty hair days! When I’m running late, I often forgo shampoo and grab a hat. First, reserve certain fabrics/textures for the seasons they are intended for- straw hats for warm months, felt or wool hats and toboggans for cooler months. Next, gauge the situation you will be in by a) the atmosphere, and b) the people you will be with. If you are shopping with your best friend, grab a hat. If you are having lunch at the country club with your mother-in-law, leave the hat. I also try to wear hats when I know I will be outside a good bit that day. Even if you work in an industry where hats are appropriate, unless you are running errands, you may look silly sitting at a desk all day wearing a hat. The most important thing is that you’re comfortable, so gauge the situation and use your best judgement.