If shyness is indeed a fear of negative judgment, one way to combat this is to find activities where the focus is not on engaging in conversation right away, but on the activity itself.
When you join a club where the focus shifts from meeting people to doing an activity, you can engage in conversation slowly over time. You won't feel pressured to connect, but will be encouraged to do so as part of the activity which you share in common with everyone else there. Fear of judgment in this case, is limited.
Some activities to try:
Book groups: The focus is on the books you're reading and not on you. What's more, book clubs have a lot of introverts in them, which will allow you to remain quiet without feeling odd. You can add your opinions or just listen to what others shy. Either way, you'll be part of the activity and will be meeting people slowly month by month.
Volunteering: What better way to take the focus off of you than by giving your time for a cause? Helping out others also boosts your self-esteem.
Sports: Playing a sport makes you part of a team. That in and of itself gives you an "in" with new people.
Classes: A class is always a good way to meet new people because you'll be expanding your mind, learning something new, and interacting with people on projects. (Seems to me, it sounds like our English Club!)
