Like:

• The shirt. It has a subtle pattern that’s going to give it some contrast without being too crazy. He also has the right number of buttons undone.
• The shoes. Suede loafers in a natural color are an awesome late-summer shoe. They’re still appropriate to wear without socks, but will transition well into fall. Natural suede is just a good color all around anyway.
• The belt. There’s been a big push in the last year to return to braided belts. For the most part, they conjure up images of mid-90’s fashions of extra-long belts, baggy clothes, and awful hair. This is a great way to resurrect the braid though. It’s subtle and he uses it to cap off the look instead of it being the focal point.
• The jewelry. Whether it’s politically correct or not, most black men tend to have more Danger than Play in their overall appearance. By adding the jewelry it ups the level of Play and provides some good contrast.
• The beard and haircut. He keeps everything tight and modern but still has some inherent masculinity in his beard and a nod toward tradition with the part.

Fence:

• The jacket. Although it’s current to have a jacket that’s smaller in its overall proportions, I think this is something we’re going to look back on and see as silly. The body of the jacket and the sleeves are too short. Everything else about it is great though. It fits him well in every aspect besides length, the material looks like a linen – which is a good contrast against jeans for a late-summer look, and the color goes well with everything else he has on.
• The jeans. The color is exactly what men should be looking for when they want a pair of everyday-wear jeans. Unfortunately, it looks like they’re just a bit too small. They look tight enough in his thighs and calves that I’m betting they restrict his movement. They also would look better with only one roll. I like exposed ankle in the summer, but the extra roll paired with the smaller proportions of the jacket just make him look like a giant who couldn’t find clothes in the right size.

Don’t Like:

• The bag. The concept is cool and I’m digging the wooden handles, but it’s too purse-like. Sometimes you have to be willing to abandon a cool idea because the end picture isn’t what you were hoping for.
• Too much. He has a bit too much going on. Instead he should have followed the rule of removing one thing. Whether it’s rolling the pants down, getting rid of one arm’s bracelets, or ditching the pocket square, he should have gone a bit more traditional in at least one more aspect.

PS. Have you gotten your Style Evaluation? It’s a great way to know the strengths and weaknesses of your current wardrobe.