One of the Gurus has said your concealed weapon should not
be comfortable. It should be comforting. I have always thought
why can't it be both?
I think that when he wrote that concealed carry was more difficult to do. Few states were 'shall issue' and most required some immediate 'need' that you had to demonstrate before they would issue a concealed license or permit. Concealed in those days meant undetectable, and undetectable isn't comfortable.
Today, with almost all the states being 'shall issue' and without 'need' requirements, as well as recognizing open carry, most people (police officers included) aren't going into a tizzy over the sight of a poorly concealed handgun. In Washington our courts declared that a police officer cannot stop someone and demand to see their CPL merely because the officer or someone else observed a poorly concealed pistol (the rationale being that concealed carry pistols are legal, and thus insufficient grounds to conduct a Terry Stop). Concealed means what the word means; obscured from view. Comfort and concealment are no longer mutually exclusive.
Which is all to say that yes, you can have both....now. If you wanted to conceal under a tight white t-shirt beneath which the gun can be easily discerned (not sure why you would), you're still legal. Given this liberty, if one is carrying uncomfortably it is by choice and due to their own insecurities. They'll blame it on things like "the law says..." or "I prefer to surprise the bad guy" or other similar nonsense, but in the end
in most states it isn't necessary or even desirable to carry with deep concealment in most situations.
EDIT to add: I'm 5'8" and medium build. My EDC is a 1076, 1911, Sig P229, or Sig P320 OWB as comfortably as one could, and concealed as much as is necessary. I don't carry a .380 or other tiny gun because I don't believe they are suitable for much other than bad-breath distances, and I don't want to be prepared for
only that scenario.