173: Self Love Secrets From a Bra Fitter with Kimmay Caldwell

On this episode we hear from Kimmay Caldwell, an Undergarment Educator and Coach, whose 20-year-old self, working as a bra fitter, was struck by how people viewed themselves in the mirror. The harsh narratives people came up with while trying on a bra made her transform her own relationship with her body. Now, Kimmay supports all those people who struggle with self-love, self-acceptance and body image through her coaching work. Kimmay covers everything about loving yourself and owning your body.

Becoming a self-love coach and an undergarment educator

Kimmay was an independent and struggling full-time student in New York City and became a bra fitter at a bra shop in Soho where she met all kinds of people from different backgrounds. In the pre-Instagram period of hiding cellulite and stretch marks, Kimmay (like many others) struggled with body image and self-acceptance. Being a bra fitter gave her a window into the most vulnerable parts of people’s minds- what they see when they look into the mirror. The negative stories that people came up within that intimate space made Kimmay reflect on her own relationship with her body. It not only inspired her to improve her perception of her body and image but also inspired her to support others in their own journey of acceptance and love.

Kimmay says that breasts and genitals are the most intimate and sacred parts of our body. However they appear – full breasts or a flat chest, it centers our energy. When people feel shame and discomfort with those parts of their body, it can throw their energy off.

How did Kimmay help as a bra fitter and now as a coach?

Working as a bra fitter in retail, Kimmay would encourage people to see something positive when they experience intrusive thoughts like what their bra size means to them. Now as a coach, Kimmay started with bra fitting sessions where she addresses three things – confusion, discomfort and shame, to get people to start liking what they