If you run into anyone you know deal with it then, not before.
Go for a short walk, check the mail. Anything then go one step further.
And if you are out and about in drab, think how many people to you see that know you. If many shop where you shop, change when and where.
And when you go for the big one, I agree, take a friend if possible. I did that when I first started, but now I go where I want, when I want. Most who know me now know anyway.