The details in this seem really off and fake to me.

If Roger wore a white or blue LL Bean button-down every single day, would LW notice? (It is entirely normal in my Yankee experience of a certain class of men (and they do tend to be the golf-playing ones) to have a dozen identical or nearly-so shirts that they wear for work. In many cases, the shirts are rotated through a cleaners weekly.) In certain tech circles, the wardrobe of identical tee shirts is used as a group identifier showing how dedicated to purpose and free of extraneous distractions the male wearer is.