Ryan asks: I try to at least wear button-up shirts the majority of the days, the problem I have, however, is whether or not to wear a white t-shirt underneath of them, or to wear a v-neck so it’s hidden, or none at all. Any help would be much appreciated.
The matter of whether to wear an undershirt is one of personal choice. Wearing an undershirt will extend the life of your shirts, and may help absorb sweat that would otherwise be absorbed by your shirt. Some sweatier men prefer to wear them at all times for this reason. With an undershirt, you’ll generally be warmer. In cool weather, this is great. In warmer weather, it might not be. Again: personal preference.
One mistake you should never make is to show your white undershirt. Take a look above, at the guy who’s artificially inseminating a glass of wine. Not cool. If your shirt collar is open, we should see your neck, not your undershirt. Undershirts are underwear, and shouldn’t be seen. If your collar is open, go v-neck or go without.
Of course, a colored undershirt can be worn as a contrast layering piece under a casual shirt. This is particularly useful when the shirt on top is actually a casual shirt for layering, like a flannel in early Autumn. This look is easy to mess up, though. One false move and you start looking like a guy in a television commercial for breakfast cereal.