These shoes are dressy enough to go with a suit (I got the black with the brown stitching) and with business casual (e.g. nice slacks and shirt).  The AE site talks about them going with jeans, but I don't think the look is right for that.  I was worried when I ordered them that they would be too casual and not be able to be worn with a suit, but I was relieved when I saw them on and with nice blue, grey, or black dress slacks.  They are not a young man's look, but I doubt many 25 year old's are wearing $300 AE shoes anyway, even though they probably should as they would last them a long, long time.

An important note on these, which relates to the sizing.  Order a full size smaller than what you would normally wear.  For example, in running shoes, I wear a size 11, and in some dress shoes I may wear a 10.5.  I knew these ran big so I got the 10.5 instead of 11.  Wow, they were just too big.  I returned to AE - and their customer service is excellent  - and got a size 10 and they fit great.  I have been wearing J&M shoes for 20+ years but am switching out to AE shoes when I buy new ones as AE's are made right here in the good ol' USA.

A minor note, you should use saddle soap on these instead of black polish, as the black polish would stick to the brown stitching and ruin the look of the shoe.

$300 may seem like a lot for a pair of shoes, but if you treat them right, such as using shoe trees, they will last you 15+ years.  Great product.  The matching belt is the Lamar, which is about $100.  Note that the belt is 38mm wide instead of 35mm so it is a little wider than a normal dress belt and may not fit your belt loops as well in your pants.