Some people would consider a person to be "badly dressed" if ze were to attend a glamorous cocktail party or function wearing dirty old pajamas. In this instance, "badly dressed" signifies a misalignment with cultural conditions and expectations.
There is very little rhyme or reason or logic to the cultural practice of wearing neckties. There is a fabric-based language, a symbology, a semiotics in use in the workplace, where necktie-encoded subliminal messages about power and position and personality are constantly being transmitted and received.
And yet, and yet and yet. In the context of self-actualisation and personal growth, the more one is concerned about physical appearance and accoutrement such as clothing, the less one could be said to be enlightened (at least within some discourses). Ghandi for instance was never friendly with Calvin Klein: the one died before the other was even born. Nor would the Buddha have given much thought to the style and fabric of his loincloth.
And yet, and yet, and yet. Isn't it true to say that the discourse in which a 'higher' 'value' is placed on becoming self-actualized or enlightened vis-a-vis enjoying a good meal or a good fuck, say, is itself context-dependent and relative? And therefore susceptible to being judged by some to be 'stupid' or 'meaningless' just as the wearing of neckties in the workplace is judged by some to be stupid and meaningless.
Words are like a one-shot disposable syringe. They only have the meaning we assign to them when we use them, as Humpty noted.
Which leaves us washed up high and dry on the drear shores of meaninglessness, enslaved by our own choices and contexts, and self-deceived by the trickster going by the name of Free Will.
But there is a way out. And it's really very simple. Here`s the way out: don't be surprised by the outcomes of your choices and don't complain about them either. Or do complain, but then don't complain when your complaint fails to achieve the outcome/s you seek. Because you become a serial whinge-bag and acquire a taste for it, and then pity everyone around you.