A lot of people seem to find success in carrying concealed while in casual sweatpants or beltless shorts by using a holster with some form of clip that snags the fabric. While I know a number of squared away people who make this work on occasion, I have never liked this solution myself. I find that wearing a gun in this manner leaves me feeling vulnerable to the gun/holster combination falling out of my waistband under vigorous activity. I also find that an elastic waistband or draw string, no matter how tight, does not put enough tension on a holster wing to make the gun conceal properly. The gun also floats up and down with changing positions, and I have also found that the holster can actually change positions, or even flip inside-out, upon drawing the gun. for these reasons, wearing a gun in a holster that is clipped to any sort of pants or shorts with no belt is a no-go in my lifestyle.
Rather than rely on clipping holsters to elastic or draw string waistbands, I have long found belly band solutions superior. Now, the Phlster Enigma seems the obvious choice here. The Enigma accomplishes several things that a holster, clipped to a drawstring waistband, cannot do; first, it holds the gun far more securely. Second, it does not allow the holster to move around or to go along with the drawn gun during the draw because the holster retention outfights the draw string tension. Third, it provides belt-like pressure against the wing of the holster to make it conceal far better than anything attainable with a holster clipped to an elastic waistband or drawstring.
The ability to simply clip a holster to the waistband of beltless pants is very convenient, but it leaves a lot to be desired concerning retention and security. Worse than a kydex holster that clips to the pants is the use of Sticky or Remora holsters that are simply shoved into the waistline. Such sticky holsters can we useable with sufficient belt tension, and work well for pocket carry, but using such a holster with only a draw string is a no-go.
In order to dress casually in beltless pants, look no further than the belly band solution, or better yet, the relatively new Phlster Enigma or a similar solution. Such a device provides all of the functionality of a belt as it relates to the holster, yet eliminates the need to wear a belt on the pants. A carried gun must be sufficiently and securely retained on the body even during vigorous activity and I simply don’t see how that is possible when affixing a holster clipped to sweatpants or beltless shorts.