Like:

• The fit: The jacket is a bit slouchy – which actually works because it’s a casual jacket and it’s still not too big. It also is a thinner jacket and that will mitigate the extra sizing. The shirt is the perfect length to be worn untucked and the pants look like they’re slim but still with enough room to move around.
• The texture: Flannel shirt, quilted nylon, and what looks to be a rougher cotton for the pants – all of these play off of each other very well to give some textured variety to the looks as a whole.
• The coloring: All these colors are fairly analogous to each other. There’s still some contrast with the white in the shirt but this could very easily be worn by a man with a moderate or muted contrast.
• The bracelets. They’re subtle but still there and visible. It’s just a hint of attention seeking without going overboard.

Fence:

• The watch: It could be good contrast that he’s got some dorky digital watch on his wrist – or it could just be incongruent and look stupid.

Don’t Like:

• The pocket square: The way he’s wearing it is too crazy even if he were wearing a suit. Since he’s trying to pull it off with a casual outfit it needs to be much more subtle. A TV fold would still make it work. This is attention seeking by going overboard.
• The buttons: Still has to undo that second one. It would show a bit more skin and keep the focus on his face better.

PS. I’m having a holiday sale. You can get a Basic Consultation for only $15 and that $15 applies to new clients pursuing Event or Online Consultations as well.