Conservatism filters clothing from status signals, making other signals relatively stronger.
Designer suits, Savile Row suits, and bespoke brogues are among the most expensive garments men can buy. Surely there is status signalling involved in conservative fashions. Granted, the logos are typically less conspicuous in formal, semi-formal, and business attire, but doesn’t that just signal refinement?
Designer jeans and expensive basketball shoes were largely unheard of until the late 1970s. The peacock signaling that you associate with clubwear may just be an artifact of the fact that human leks now take place in nightclubs more often than in Débutante balls.
There is also the trend wherein yesteryear’s formalwear becomes the clothing of today’s servants (think tailcoats and livery) while yesteryear’s sporting garments appreciate in status. For example, the sportcoat was originally a hunting jacket. The blazer, too, was associated with sport. Brogues (AKA wingtips) were once outdoor shoes.
One doesn’t necessarily “sidestep fashion” by dressing conservatively. Desired lapel and tie widths change over the years. Do you care if your clothes have stains or holes? That signals something about your fashion sense.
Figuring out which clothes appeal to the shifting tastes of various audiences in various social settings is not easy for someone who suffers from schizophrenia, autism, trisomy 21, severe depression, or other affliction that impairs one’s will or ability to conform to mercurial social trends.
Even someone who buys desirable brands can be inept at coordinating garments and selecting an appropriate cut. Like many other social behaviors, the clothes we wear send messages about our social roles, aspirations, and neurological health.