Different perspective here...
Sometimes it's better to be clearly different than slightly different. As in a real suit vs. mismatched separates - the onlooker can get preoccupied with trying to distinguish. Also, burgundy with burgundy is rather matchy-matchy. Therefore, it probably would be best to individually mix the AE items with brown items.
Re the ankle boots pictured, the black, smooth texture, and sleek shape each increase its formality. Treat it like a pair of dress shoes - wear with a button-front shirt and dress socks. Jeans to wear with it should be dark and plain.
Uh, that's plenty of information but no pictures and few obvious limiting factors.
Upgrade the footwear.
[lose weight, please, before the next steps]
Buy some patterned shirts, such as gray gingham.
Buy some interesting, quality belts.
Wear quality jeans sometimes (but not with conservative customers).
Hair type, facial features (jaw, nose, forehead size, and so on), coloring, personality, typical clothing, age, etc. Think about that when judging whether very long hair looks good on a particular guy. Still, basic ingredients might not make a successful recipe, and an impressive hairstyle often comes from trial-and-error and feedback (especially from hair professionals).
Many people run around with bad haircuts offline. Even on Style Forum, some people display poor aesthetic taste, and of course new members are notorious for being less knowledgeable than veterans.
Some reasons people might have trouble assessing their own hairstyles are year of wear/being accustomed (research indicates that familiarity is attractive) and no easy way to instantly compare with an alternative (like an identical twin with a different haircut).