Depends on how it’s done. You could go the 90’s throwback route with the bucket like my man Larry June...
People don’t have style these days, they approach getting dressed like how a baseball card collector shows off their most expensive cards.
Just because something has high retail or resale value doesn’t make it a quality piece of clothing or make it a timeless style piece. Long sleeve polos are good for layering in the fall. Layer it under a leather bomber, denim jacket, M65 army jacket etc. If you 30+, you shouldn’t be looking to the under 25 crowd for fashion advice anyway, they haven’t even found their style yet and their style is nothing but logo hoodies and hyped up basic sneakers like Jordan 1’s and Dunks.