I discovered my gynecomastia in perhaps an unusual way. While canoeing, wearing a life vest, the day ended with chest soreness and irritation from the rough synthetic outer material of the vest. This raised my consciousness about my chest and soon after shoulder seat belts became an irritation - or better described as an inappropriate sensitive pleasure at the wrong place and time! I tried covering with BandAids (plasters) but removal was painful - there had to be something better!
And so began a similar progression with bras over the last 8 years: initially Amazon for sport style pull-overs and the local Jockey or Hanes/Bali outlet for similar. I screwed up my courage then one day and stepped into a Lane Bryant and was measured 44B by a sympathetic SA. I stepped away with my first cupped bras. Next the local Kohl's knowing my real size (which is hard to find). It's easy to grab a few bras there and slip into a fitting room as the staff is usually working stock, and no one is really paying any attention! Initially I had some help from my wife selecting a few garments. Torrid was next. They were welcoming and helpful - particularly if your arrival is during a lull in business. I measured a 42B. I was in the process of loosing weight over time, and felt like I was headed out of their larger sizes. Eventually, I stepped into Soma. I found sympathy and was welcomed finding several 40B sizes that fit. This began a long relationship with the staff at three Soma stores. I also tried Victoria's Secret and found a similar welcome and help, but little stock to fit. With my weight now well under 200#, I tend to go back to Soma now fitting 40/38 B/C. I usually wait for their sales which make prices almost reasonable, and visit during quieter times of activity. What has also helped has been keeping a few notes to remember SA names and physical descriptions as well as what has worked and what has not.
I now appreciate why women are overwhelmingly in the wrong size, and otherwise hate bra shopping! It's tough to find what fits as there have been so many that do not. Top it off, confusing sizing and measurement methods have injected additional frustration. Oh, there's just the plain fact that attempting to simply measure inherently 3D breasts with two linear dimensions is just simply ludicrous!
And, it's just a journey down one of the side streets of life!