This is the thing about dressing. You are not just covering your body. You are sending messages to the world about who you are -- your social class, your aesthetic preferences, the degree to which you are tuned into other people and the people you feel most comfortable with. You are sending messages about what you think of yourself and what you value.
So here are the messages -- good and bad -- that you can send with your clothing choices. These hidden messages are the reason I don't always find well-dressed men more attractive than poorly dressed men. Each group has some drawbacks and some endearing traits. Although I notice the way a man dresses, I don't value it enough to have it be part of my criteria for dating, so I've dated men in all three categories -- although the personality traits I like tend to attract me to Category 1s and Category 3s more than Category 2s.
1) Category 1 men -- well dressed men: They are aware of what they look like. They notice details -- drape, texture, color -- and can make choices about which ones and which combinations will fit them and convey a particular mood. They are tuned into the social world and know how to convey a bit of personality through their clothing -- and this indicates a larger sort of social fluidity -- a man who knows how to dress is probably a man who knows how to act in different social situations, who is sensitive to ways to blend in and ways to stand out. They have an aesthetic sense and recognize the impression that their appearance makes on people. They know what looks good on them.
They may be vain. They may be high maintenance. They may be fussy. They may be perfectionists. They may be shallow. These are the red flags I get from some well-dressed men. I find vanity and fussyness very unattractive. So I like some well-dressed men, but am put off by other well-dressed men.
Category 2 men: Understand the basic rules of dressing, but don't venture beyond Banana Republic or the Gap or some other corporate decision maker to determine taste. These men are tuned in enough to recognize and avoid the big fashion gaffes that are possible. Their clothes fit and flatter. But they are either too disinterested or too cowardly to make any decisions for themselves. They are conformist. They will not look clueless, but they don't seem to have a strong aesthetic of their own, and they are afraid to take risks. These are the blue button down, khaki pants, grey sweater guys. They look fine, and they get social situations. They know how to fit in. They strike me as boring. But they're often attractive enough, their clothes are flattering, and they've got a social radar. They're adults, they can navigate the grown up world and do just fine, but they're not leaders, or innovators, or blazing any trails.
Category 3 men: They're either naiive or arrogant in believing that clothes aren't worth any attention, and that dressing doesn't mean anything in particular. They either don't have an aesthetic or are lazy. They don't recognize the social messages they are giving off with the way they put themselves together. That may indicate that they don't pick up other social signals. Will they feel awkward at a fancy wedding, or a beach picnic -- someplace out of their usual element? These men are often sweet. They are not vain. They are not fussy. They are agreeably oblivious. They cling to things that they like, for sensible or emotional reasons. "It's really soft." "I've had it forever." They're loyal.
I believe, firmly and deeply, that you cannot and should not try to change somebody else. So if I date somebody who is a Category 3 kind of guy, I accept that he may always be a poor dresser. I've dated several of them and except when asked (e.g. "Which tie do you think would look better for this wedding,") I stay out of their clothing choices. It's not a big deal in the scheme of things. But a guy who can dress wins points for sure.