The most important question is “when” to distribute jerseys. The tongue-in-cheek answer is: whenever you no longer need leverage. You’ll want to make sure you have these things complete:
In addition, be mindful that players can be switched around at the early part of the season due to practice conflicts and other reasons. So generally you want to wait until 2-3 weeks into your practices anyway.
When you’re ready to hand them out, you should realize that some players have really strong attachments to numbers. I’m not saying you need to accommodate them, but, however you distribute them should be seen as fair.
Disclaimer: I always let coaches players get first pick. Considering they endure the unfair burden of having their dad/mom coach them, I think that’s a fair reward.
It’s a good idea to let parents know (maybe by text that day) that you will be handing out uniforms at the end of practice. This ensures the parents are there and standing around to assist you as needed.
After practice ends I have the players line up shortest to tallest, then hand out the uniforms from lowest number to highest. The higher uniform numbers are the larger sizes. Almost no ones will fit perfectly but it ensures the least disparity in size. I communicate why I’m doing it this way, and that the players are welcome to trade their jersey with a friend as long as parents agree. By the way, you want the parents there so that if the player loses the socks or something they can’t say they never received them.
I also will ALWAYS get the question: “How come so and so (the coaches daughters) aren’t lining up”. I just respond truthfully that because I will yell at them (my child) on their field more than any other kid, picking their jersey is their one reward for the season. Seems to have never been an issue from there.
Protip: After the players have their jerseys, ask that they TRY THEM ON over whatever they wore to practice. Otherwise sometimes you will have a player that tries on their jersey the morning of first game when it’s too late. As a bonus, take your first team photo together with your players in their new uniforms!
That’s just the best way I’ve found, I’m sure there are other equally good ways, feel free to drop your favorite in the comments below.
Final note: If a parent is adamant about needing a different size, email firstname.lastname@example.org for assistance. Do this asap as lead times can be a couple weeks.