I have been away from Dappered for a while...but I got a new job as an assistant principal and I am looking to make a few upgrades to my wardrobe, shifting to a bit more of a shirt and tie look. I have been searching for years for a plain black pair of shoes. I checked these out at Nordstrom today but felt the toe may be a bit too "boxy." I am digging the boots that were on the front page today. Also interested in these for something slightly more casual.

I am really struggling with pants. I have always worn the Jcrew Broken in Chinos, but that won't be quite dressy enough. I snagged a pair of the Ludlow 4 season wool pants on super sale today, I am interested in a few more pairs of wool pants or a dressier option than the chinos I used to wear. I picked up a 3/99 deal from Charles Tyrwhitt, going to make sure sizing is right before ordering any more from them.

TLDR...New job = new wardrobe, need black shoes/casualish brown shoes, dress pants...

Thoughts?