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Man, it annoying me that nobody is qualifying their statements. Advice given like this is absolutely useless.

That not a dress shoe, it a driving loafer. They not even remotely the same thing and fill completely different roles in your wardrobe. Your confusion here is totally understandable what is not is people rejecting the shoe without explaining what the difference is, or why it meaningful (it is). Driving loafers are virtually impossible to find without some type of rubber sole. That completely okay for that type of shoe. Having said that, I think those particular drivers are kind of bad looking and wouldn favor them over other, cheaper pairs.

I also think telling a person they should just “avoid dress shoes with rubber soles” is dumb. Don do that. Shoes with leather soles, aside from being inappropriate in certain weather/climates, also tend to require more upkeep, cost more, and be less sturdy if you care about that sort of thing (in the winter, I do). If I were buying a nice pair of shoes, I probably shoot for leather soles, but there a place for less expensive dress shoes with rubber soles that Air Jordan 7s you can wear without concern in the winter and rainy seasons, and if you have a need for that, don let anyone talk you out of having a pair (albeit, maybe, a nicer looking pair).

Look at those Staffords that people here, myself included, are fans of. I own them, as well as a few pairs of AEs. Guess what? I think they look nice, I can wear them year round, I don worry nearly as much about maintenance, they more comfortable than AEs, and they grip better. I personally think the shoes you posted with your suit look pretty bad (though the colors are fine, imo), and the stitching and chunky black rubber sole are a big part of that, but the Staffords have a synthetic sole and manage to look pretty slick.

The brick red sole is completely appropriate for a suede buck. This is a kind of modern saddle shoe variation on a suede buck; but the modern aspect, free of decorative detail takes character away from a shoe design that is based on lots of character cross purposes. The brown, stitched welt is also awkward, as it doesn match any of the colors used.

The cut off inner heel corner is called a gentleman heel, gentleman corner, or gentleman notch. It one of the details usually found on higher quality shoes, and it meant to keep your pant leg from catching Jordan Pro Strong on the heel when you walking. They do a good job of hiding it, so I guess my question is: is it objectionable to have obvious, visible padding, or any Air Jordan 9s padding at all?

Interesting Air Jordan 6s that, despite misunderstanding my question, you still provided me with valuable information.

I thought the gentleman corner might be for protecting the Nike Air Foamposite One other shoe, but I didn think about catching on the pants hem. Thanks!I think the color of the shoes could work with that suit. Essentially, it looks like you going for a brown or burgundy shoe to complement the suit blue ish grey, which I think is totally doable.