The only time I've really done that is on holiday, where I left the apartment, walked about 250 m down a lane, through a carpark, and then around 2.5 km to an unofficial clothing-optional beach. Admittedly it was pre-dawn and I had to carry something for the return trip in daylight (shirt, swim brief and cap), but the outbound trip always had the chance of an encounter.
Why carry more than the swim brief?
Yes, I've had this fantasy for years. I walk daily. Sometimes my walk is what I call a short walk for about a mile my other walks can be up to three miles. They are all in the heart of a residential, and small business districts. Many times, as I am walking, I think about what it would be like to be naked. I try to wear minimal and loose clothing. When I'm passing people on the sidewalk, I want to stop them and asked them what they would think of me walking naked through their neighborhood.
It's not illegal to be nude in public in Seattle but if a so called "KAREN" decided that I was being lewd (which I would not be) and called the police they HAVE to respond. Then it could get complicated from there and not worth the hassle.
There is a local pub that will allow nudity and this is where I get my public nude fix around cocktail hour. I'll go down there and meet other nudist friends and have a beer or two. I might even venture outside on the sidewalk for a photo op (see my photos).
It's not walking freely down the street nude but it's the best I can do.
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