Technical/Luxe messenger bag. Something with a stabilizer strap. Something that looks good and is an "iconic" traditional shape, but also weather-resistant and practical. 25 liters and up would be cool.
SIze zips you can polish and dress up, thicker stacked sole and water resistant?
Cotton mid length trench, leather accents, horn, etc.
Mixed-material jackets? Leather and wool but NOT varsities.