1. New clothes are terrible. They are stiff and take time to wear in. My wife is constantly after me to get rid of existing (sometimes tattered) clothes that I like.
2. Societal expectations of fashion seem a little pointless to me. I spend sometimes 10-15 minutes just staring into the closet every morning trying to figure out what to wear. After a few minutes my wife usually glides in, snags shirt/pants combo, hands them to me and then flits away like it it was nothing.
My perfect wardrobe is sets of the same comfortable, workplace appropriate upper/lower garment combination that I can grab and not worry about every morning. I want my 10 minutes back. 
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"Crime and punishment grow out of one stem. Punishment is a fruit that unsuspected ripens within the flower of the pleasure which concealed it. Cause and effect, means and ends, seed and fruit, cannot be severed; for the effect already blooms in the cause, the end preexists in the means, the fruit in the seed."
-- Ralph Waldo Emerson