There was a world record skinny-dip attempt near where I live and where many first-timers take part.
British Naturalism has several nude runs and mass skinny-dips for charity in which many first-timers take part.
Why not search for such events in your area? You will not only "Break the ice" but may also find some nudist friends.
I started by going to a nudist beach and stripping off, strange that the textiles who remained were the odd ones
At the textile beach I go to, most of those who are not nude are usually either with someone who is or not wearing enough for other local businesses, i.e.. women who are topless or either gender wearing G-strings.
At Sunnyside, among those that don't completely disrobe are those accompanying someone who's totally nude, locals who walk through the nude section as they are (there are some residences within an easy walk) but occasionally there are some who do wear a suit. Perhaps they are too shy to take the last step or they feel they can only wear their preferred swimsuit there rather than one of the multitude of textile beaches. Strange, since I often wear far more skimpier suits to those textile beaches!
At Sunnyside, among those that don't completely disrobe are those accompanying someone who's totally nude, locals who walk through the nude section as they are (there are some residences within an easy walk) but occasionally there are some who do wear a suit. Perhaps they are too shy to take the last step or they feel they can only wear their preferred swimsuit there rather than one of the multitude of textile beaches. Strange, since I often wear far more skimpier suits to those textile beaches!
Gunnison is between a bird sanctuary and a very lightly used beach, so there is very little walk through traffic.
After a life of clandestine solo nudity, one day an opportunity presented itself. I worked on a large diving boat in the Gulf of Mexico in the summer months as a Scuba Divemaster. One summer the boat had mechanical problems and would be delayed two days. I called a nudist resort some three hours away and found they had overnight cabins and would allow a single male. I found others who also loved to be nude, and were not shy about it. The initial shock of presenting myself naked was terribly exciting, and it showed! It was the best two days of my life, conversing, swimming, playing sports with other nudists, something I will never forget!
As others have said, just be nude. After a while you forget about it and get preoccupied with daily life. And keep a long shirt handy when you have to go outside. I'm sure that I'm not the only one here that has taken out the trash while forgetting to dress.
As for Marie and I we went to a place called Verde Hot Springs in the national forest of Arizona USA. It was a place we heard about that have naked people, and we thought it would be a great way to start.
It took Marie a little bit longer to relax enough to take her top off. Lol I immediately dropped my shorts as soon as we got there. She was kind of mad at me for getting naked so fast. But she took her knee bottoms off. Other people finally convinced her to take her top off. Its not easy for a woman to believe that they are beautiful after having a child. But she finally understood and has never looked back.
Nude beach for me too. Firstly, early morning (lucky I live in a generally warm place), with few people about, then later in the day. Strip off, sit, walk along the water's edge, gradually encounter people and find that they, also naked, behave just as people do in the street. 'Hi, nice morning' 'Yes, perfect day, cheers'. And so it goes...