Like:

• The sweater – it’s light and a bit looser than what you would want to wear under a suit but still fits well. Makes it a perfect casual sweater. The light blue is a summer color but contrasting it against the darker pants helps make this whole outfit look like a seasonably-transitional ensemble.
• The pants – They’re colored but they’re not too loud. Not only does this work better with his complexion, it helps them have more of an Autumn appearance. The fact that he still has them rolled up means it’s still summer and he’s not jumping too quickly into cooler-weather wear.
• The shoes – saddle shoes are the epitome of High/Low in footwear. They’re traditional and they’re dress shoes, but they’re so loud that they have to be casual. The off white color against the red means these can be worn well into fall and the red itself picks up on the red in his skin to make it look healthier.
• The bracelet – The red has the same effect as the red in his shoes. It’s also there and casual but still minimal.

Fence:

• The shirt –  It looks good matched with this but I can’t tell much about the pattern and whether or not it would flatter him on its own.

Don’t Like:

• The hair – It’s a bit boyish and needs to be longer on the top.
• The beard/scruff – I like the scruff look but his is too long to be scruff and too thin to be a good beard. He should trim it down a bit.

PS. Today is the last day to get the discount on Basic Consultations. Jump  on it.