Recently, my boyfriend stopped working in an ultra-casual tech environment and started working in a professionally attired downtown legal office. We have successfully found him some nice clothes, but we're still hung up on shoes. He has one pair of shoes to wear, which is basically one step above an all-black tennis shoe. We really need to find him some professional shoes that work well for his comfort and commute needs.

Some specifics:
He has very high arches and sometimes needs inserts (not orthodics, though.)
His foot size is on the small end - around men's size 8
Budget is a concern - he'd prefer to spend no more than around $100 for a shoe, so that's *around* our price limit.
He rides the bus to work and walks around downtown during lunch, so although he doesn't have to walk that far, it is important.
My impression is that his feet are pretty fussy (his dad has similar feet and has a lot of pain/arch issues) and he will not wear shoes that he doesn't find comfortable, at all.
Edited: Aesthetically, he prefers a matte shoe and nothing too fussy/fancy. We'd probably pick a black shoe first, but he might add a brown shoe to his wardrobe eventually.

We actually found an excellent shoe at Nordstrom a few months ago - I *think* they were Allen Edmonds, but I can't remember for sure - but the price (around $350) was deemed to be much too expensive for his preferences, even though I offered to split the bill as a gift.

I'd welcome any ideas that you have. I'm also hoping to take him to the NAS and see if we can potentially find a hot deal on shoes that work well for him.