Like:

• The shoes – I can’t tell if they’re bucks or boots, but they’re more dressed up than the rest of the outfit and it gives him a better High/Low look
• The scoop-neck T – It’s like a V-neck but more rare and unique. I would love to be able to find these somewhere that doesn’t charge $60 for a T-shirt
• The shaved head – There’s a go-to-hell attitude that comes with a man who has a full head of hair deciding to shave it. Not advisable in winter
• The cardigan – Adds an extra layer and frames him like a jacket but it’s still casual because it’s only a sweater.
• The coloring – A lot of neutrals but there is still some moderate contrast to work with his complexion. The shoes stand out but not enough to distract from his face.
• The leather – Both the watch and the belt add some darker brown and play off each other.

Fence:

• The fit – The shirt looks good in that position but will most likely be too short if he moves at all.

Don’t Like:

• The jeans – Not a big fan of the washed look.

PS. Don’t forget I’m running a deal on Basic Consultations all month this month as a back-to-school special.