Yes. As in, I do all of those things under different circumstances. When I know I don't want to be rushed the next day, I'll pick out my outfit the night before and place it on my valet. I do have some regular rotation type of pieces that I wear each week. Most often, though, I have enough time to let the day's activities, weather, and mood determine my outfit.

For me, hats are both functional and a personal preference. As a result, I have over a dozen hats and over a dozen flat caps.

Top notch, my friend...

I don't mind the shirt choice - even wearing it with a tie, especially sans jacket - but I'd probably go with a solid tie to keep from adding to the busy-ness of the shirt. There are some fit and execution recommendations that can be made for this outfit. Technically, the tie is too short - it should hit the clasp area (belt-buckle area) of your trousers. The shirt collar could benefit from some collar stays, as they're turning under a bit too much. The overall fit of the shirt is good. You may have noticed that there's a little poofiness around the midsection. While the natural reaction is to attribute this to a little extra padding around the midsection (which most of us have), I would attribute it to an incorrect trouser rise. The rise on those trousers is fairly low. I would recommend trying trousers with a proper rise - at the natural waist - with that shirt. It will do several things: - Lengthen your leg line, making you seem a little taller. - Make it easier to have the tie at the correct length. - Remove (hide) the poofiness from the midsection, making you look slimmer. - Cover a bit more of the shirt, reducing the busy-ness a bit. - Allow you to step up the outfit with suspenders! That last one's a personal preference but a pair of dark brown, leather suspenders with a closely-matched pair of leather shoes combined with a solid dark brown tie would look excellent with that shirt and, of course, the aforementioned higher-waisted trousers in charcoal or navy.

You can get some made-to-measure wool trousers from Proper Cloth for under $300: https://propercloth.com/tailored-clothing/navy-wool-dress-pant-698.html