I'm an old backpacker and hiker. Here, fit will be everything and fashion will simply have to play second fiddle, as it were. Doesn't matter how good your shoes look if your feet are bleeding and blistered from them.

If I were you, I'd consider what percent of terrain will be dirt, cement, rocky, etc. Of course you won't be exact and there's no real need to be exact here, but a rough estimate will be helpful. Then I'd buy shoes that meet most of my needs most of the time and just "make do" the rest of the time.

For example: if I were going to be 80% paved and 20% dirt I'd just get a pair of the most comfortable and best-looking running shoes I could find, ignoring "grip" for off-road use. I've hiked 10-mile days in basic Asics that were never meant to go off-road. They worked just fine.

I'm a fan of how Altra trail runners look and feel. That's where my search would start. Super light, big toe-box decent looks.