Choosing the color was quite easy. There was a black option - a NO for me, I already have black hats. Then there was burgundy. A beautiful color but I found it too predictable I guess. Plus, Ive already got a bright red fedora thats almost 15 years old now but still going strong. So then there was this brownish taupe color. I really liked it on me and with my style going in a softer direction plus the price beeing very reasonable I just gave it a go. As the weather has been so hot for the last days I havent started outfitbuilding but it worked with the navy coat and, I don't know, I just trust my feelings that somehow it will work out.
With hats its usually that way. I just see something, put it on and when I like what I see I run with it. Hats add so much persona to what youre wearing - so I always try to find something thats fitting for me rather then working with everything, beeing fashionable etc. The ones I bought for these reasons seem to gather dust and sadly dont get worn much.
Come fall I put my hats on a shelf at the front door and grab one that fits my mood that day. If they were in a closet, upstairs, I would always forget them. And when I go inside I put them on a coat hook or maybe a window sill. Plus - women can keep their hat on in more situations then its suitable for men. That helps too.
And I relly like the one your trying on in the first pics. Would it fit with your lifestyle? Regarding the commute - this one is not that big IMHO and carrying a bag will usually require more space on the subway then any hat one will reasonably wear on a daily basis, except one would have an official position at a racetrack me thinks ;-).