This topic, I will admit, has all sorts of potential for humor, but let's see what a serious take will get us, okay?
I think that there are lots of ways to go on this one. Suppose a man dresses like the cover of GQ and always looks sharp. To me, this means he is a sharp kind of guy concerned with details. However, it can also mean that he is a shallow guy only concerned with appearances. I have to be careful of that. Most of the time I take this tack in determining if a guy is sharp or shallow: personal hygiene. If the guy appears to be freshly manicured, speaks about his last facial, and has more beauty products than I do...well, let's just say he doesn't land in the Sharps box.
Now, suppose a guy is dressed in baggy clothes - jeans sliding off of his rear, underwear showing, oversize shirt covering a scrawny body. I'm not interested in getting any closer. I don't want to know where his peeps live, I don't care what video game he's playing. He's just not worth my time. I want to talk to adults, not over-grown boys still looking for someone to buy them beer. In my experience, a guy who hasn't mastered the art of the belt has no idea what is going on in the world outside of his Xbox, so I don't waste my time.
Now, suppose a guy is dressed simply in jeans, a nice shirt, and appears and smells clean. This is the guy I am most comfortable with. He isn't likely to think that he is prettier than me and might actually be worth a conversation. His clothing suggests that he is real and not opposed to getting his hands dirty. He may be an ass once you get to know him, but I'd still rather know an ass than a shallow prick, a stuffed shirt, or a hooligan. And, chances are better than average that at least I'll understand what he has to say.
Now, for the ladies.
This is tougher for me, because I have very strong opinions. A lady should appear neat and well-groomed if she wants to be taken seriously. Now, I don't think she needs to dress in the latest fad of look as though she walked off of the cover of Vogue. To me, fads are ridiculous and what passes for "women's fashion" is really a joke. A woman should look professional but feminine. I'm not talking Melrose Place and "suits" that are really miniskirts with jackets. No.
She should look put together, but effortlessly so. She should be carrying a quality handbag and be wearing nice shoes.
She should endeavor not to be caught out and about looking like a bag lady. However, I will make one exception: the grocery store. I don't think you should feel the need to dress for the grocery store. Who are you trying to impress, the stock boy? The fact of the matter is, grocery shopping is hell. You should dress for comfort, as though you might be spending six days in the trenches without a shower, rubbing up against humanity's ugly under belly. You don't want to be wearing your nice shoes in the trenches.
That's it. That's all I've got. Go see what the other Divas, Arielle and Silk, have to say. Also, check out what the Gentlemen have to say: The Maximum Leader, Jamesyboy, and Puffy.