1. If one’s shoes are broken – can one buy new ones during the Omer?
2. Can one have a new Shabbat suit fitted and made by a tailor during the Omer. I saw it brought that it is dependent on minhag hamakom and as long as one pays for it after the Omer. What if the tailor insists on a down payment?
1. Yes, there is no prohibition against buying new items of clothing in the Omer period.
2. Yet, there is no problem of having a suit fitted and made during the Omer, and one can even wear new clothes in the Omer period and recite a berachah over them. The Omer period is not a time of sadness, and on the contrary, it is a joyful time between Pesach and Shavuot. Nonetheless, we practice some customs of mourning because of the deaths of the disciples of Rabbi Akiva, but this doesn’t change the period into a sad period, and it is permitted to wear new clothes and to recite Shehecheyanu.
See Mishnah Berurah 493:2.