I feel like the top half and bottom half or jwoowoo's fit belong to different epochs
I like the thought that went behind this outfit as it is familiar to my own. The execution is off though as everything is one size too small. The only thing that seems natural is perhaps the hat and pants break.
Now when you mention "epochs" I think you are actually brand discriminating as I am sure you recognize immediately what label each item is from. Perhaps your latter thought is that Ervell does not fit with the straw hat and creepers (I don't know, just an example). However, I think we both know Ervell has used creeper type shoes in his runways e.g. Redwings postman shoes.
When I look at the outfit IMO I think 'wooo was trying to balance the top heavy with the bottom heavy, big straw hat with big platform shoes. This leaves the medium in between very empty though.
I saw that fit and I had no idea what any of it was, but thought the exact same thing as lmao. Colors/pattern/texture of the top screams warm weather, bottom does not regardless of the fact that the pants are cropped. Both cool but in the same fit don't look right.