Most correctional facilities provide standard-issue clothing, including underwear as part of the basic uniform package every inmate receives upon intake. The quality is functional rather than comfortable but it is there and it gets replaced through the facility laundry system when items wear out.
Beyond the standard issue, many facilities allow inmates to upgrade through the commissary. Better quality underwear, socks, and t-shirts are commonly available for purchase and most inmates who have funds on their books take advantage of that option fairly quickly. Commissary clothing items tend to be significantly more comfortable than institutional issue and for people serving longer sentences, the upgrade is worth it.
Some facilities go further and allow family members to send in clothing directly. Rikers Island in New York is one well-known example where sending underwear and certain clothing items from outside is permitted under specific guidelines. These policies are the exception rather than the rule but they do exist at certain institutions.
The honest answer is that the policy varies enough from facility to facility that the only reliable way to know what applies at your loved one's specific institution is to call and ask. The inmate's counselor is the right person to contact and contrary to what some people expect, counselors are generally straightforward to talk to when families have basic questions like this. A quick phone call saves the frustration of sending something that gets rejected at the mailroom or assuming the facility provides something it does not.
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