So a long-overdue update to this thread... I passed on the suggestions to my boyfriend (B) a while back and he looked at a couple places without finding much, then kind of let the subject drop. He opted to wear less comfortable but dressy shoes at the office, and wear comfortable sneakers to commute to work. As long as he was dressed appropriately actually at work, I was happy.

Well, today he came home with a pair of nice black lace-up ECCO shoes that he found all on his own! They look very nice - not super duper dressy, but polished, appropriate for his workplace, a vast improvement on the last, worn-out pair he had. Apparently they are quite comfortable with some memory-foam footbed inserts popped in.

I offered to help pay for some of the cost of the shoes, which was what I told him I'd be willing to do originally, but he said they are within budget - he said that instead, he needs more help with clothing since his wardrobe, and particularly his bus-cas attire, is still quite small. Also, Christmas and his birthday are not far off.

With his permission I'm posting pictures here. B. has some fit challenges with clothing - he's on the short side (about 5'8"), mainly short in the legs, and is a stocky apple body type with strong shoulders. He has gorgeous blue eyes and wears glasses full-time. He's several years older than I am, though he looks quite a bit younger than his age.
For his work wear it's generally knakis or black pants with a patterned button-down shirt tucked in & with a belt (Picture #1.)
For casual wear he goes for jeans, logo tee shirts, and sneakers (Pictured #2-4).
I like him best in woven shirts that are a bit oversized, and with his coloring (blonde with blue eyes) he looks especially great in blues and greens. I'm not really a fan of tee shirts in general, so I'd like to help nudge him towards a slightly more smart-casual look, but I know he prefers the comfort of tee shirts.

What would you suggest for my helping B. with the next leg of his style journey?