Is it permitted for a baal teshuva to buy his first black hat during sefira? Even if he is otherwise strict about buying new clothes during this time period, perhaps this would be deferred by the fact that now he will be able to fulfill the hiddur of davening with a hat as well as wearing a hat l’kavod Shabbos? Or should he delay his purchase until after sefira? Should he make a bracha on buying the hat? Also, perhaps the rav could offer some general advice about when is the appropriate time for a baal teshuva to don a black hat.
It is permitted. The reason being that, the inyan of davening with a hat and jacket, is based on kavod for H-shem while davening, it is better to put one on even though you don’t usually buy new things during sefira. You may also say the bracha.
Regarding when a baal teshuva should don a hat and jacket, this depends on each individual person, and the general rule would be when he feels comfortable enough to do so. He should not be forced to do so before he is ready.
M:B 493-2, PIskei Halachos (Sefira) 3-5, Piskei Teshuvos 91-3, Horav Y. Cahen shlirt”a, poskim