Q. What is the appropriate stage at which a baal teshuva should acquire and wear a hat? (This is obviously a personal decision, but perhaps the rav could offer some general guidance). Also, is it appropriate for a baal teshuva to adopt chumros and various hanhagos, and if so at what stage may he do so?
A. Horav Shlomo Miller’s Shlit’a opinion is that a baal teshuva should be close to a competent Rabbi, teacher or mentor who can guide him in his way back to Hashem and His Torah. What may be proper and advisable to one person, may not be for another. Singular and dedicated guidance is essential to the process of a successful teshuva. The Rov also compared an effective teshuva to the climbing of a ladder, if one is not to fall it has to be done step by step. (See also question 1446, 1255).
Rabbi A. Bartfeld as revised by Horav Shlomo Miller Shlit’a