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Bike people have a propensity towards collecting bike-related things, and bikes, it can get out of hand I’ve heard. It’s obviously easier to collect something small like bidons (water bottles), magazines, jerseys, musettes or caps, if it’s something useful then it’s almost possible to justify having so many of them they no longer fit in the large space allocated to them, spilling out into daily life and public areas, again, so I’ve heard.
The joy of a cap is that it’s a compact bit of kit that really allows you to show your allegiance to your favourite marque, rider, bike shop or overly-hoppy-artisan-craft-beer-producer, whilst at the same time keeping your head warm, or even cool. The Pros used to wear them all year round, admittedly partly because they were paid to do what their sponsors demanded, but also because they keep the sweat from running into your eyes, and can also keep the rain from running into your eyes too, peaks keep the sun, snow and rain out. Since mandatory helmet laws were introduced in pro cycling the wearing of the cap seems to have waned, but then if you are riding around on a 1980s bike it’s only appropriate you complete the look. They fit into a jersey pocket easily so if you are out on a ride early you can put it away once it warms up until you stop for a macchiato, just make sure the cap you take matches your bike or kit to avoid a cafe-front faux pas, they are also ideal for the promuter.
Whilst the rules (#22) are to be taken with a pinch of salt, there is something in the position that you shouldn’t really be wearing a cap unless you are actually cycling/about to ride/immediately apres ride, but feel free to do what’s comfortable, and remember you can never have too many.