The main idea is to dress up much the same way as you would dress up without pantyhose.

Dressing up

Only a very few people will notice that you are wearing pantyhose. You should communicate with your clothes and behaviour that you are not there to show off yourself in pantyhose, but rather to do your regular business - shopping, walking etc. You may also wear support pantyhose at the beginning for more "legitimacy".

Wear the same shoes that you would wear without pantyhose. Don't wear your brand new shiny shoes as they would just draw attention to your legs.

Carefully choose and test your pantyhose. The best male pantyhose is Comfilon (also known as Activskin). High quality support pantyhose (compression tights) is a good thing to start with - it's a legitim, accepted thing to wear. Decide to shave or not - when you are ready to go out, ask for the opinion of your partner or friends.

Act and behave as usual: this way you are communicating to others that you are in fact a usual guy.

Dealing with others

If you meet people you know, don't try to avoid them: greet them, talk to them, as you would do in other situations. (Well, the situation is in fact the same!)

Don't wear anything unusual (apart from pantyhose of course), used clothes are basically better than new ones, and the more conservative style is the better.