New Balance 1906L sneaker loafers - not as eye-catching as the internet suggests, they're virtually identical to regular 1906s with a wide leg pant. Run small; I'm an 11 in NB 574s/990v2s/most other sneakers and these were manageable but snug.
Vintage suit pants, judging from the tags early 90s. Incredible pants. YSL still makes variations on these every season, though the rise isn't as high.
Polo Ralph Lauren Yarmouth OCBD - as expected, an oversized lightweight button down for a good price secondhand. I sized up still (16 vs 15.5), but these are still a fuller cut then modern shirts regardless.