I have done a lot of trial and error shopping, my wife as returned some of the purchases that didn't fit for me.
I am planning on going to Soma (was to be tonight) on Monday to try on a couple bras that are on sale. Calling ahead seems to help a lot. The young woman was very helpful on the phone and considerate to my problem. I did ask if I came in could I try a bra to make sure it fit, she said absolutely. I didn't ask for a formal fitting, but I would think it would be ok to do. We briefly discussed some of the issues I am having with fit and solutions.
She said they would work out me being in a room when no one else is coming in/out to avoid embarrassment for both parties. They have been down this road before by the sound of it. I am nervous as heck, but think it will work out ok. I would like to have a professional opinion, I think I fit what size I have ok, but some bras do have some issues over the course of a day and others don't.
I have heard that Lane Bryant Cacique is also very accommodating to men who need to be fitted, but have never been in a LB store before. Some even say Victoria Secret it too, but I also haven't even thought much about trying there. Soma is known to be very respecting and helpful to men who need fitting. The bras from them are top notch quality fabrics and assembly.
Call ahead and speak to them about what you would like to do. If they don't seem to be willing to help find another store, but I think most commissioned sales will be helpful.
I have plenty of sports bras, but don't like them for daily wear, they do flatten, but it does get uncomfortable for a long time wear. Most cotton shapeless sports bras do very little to support, they do more to just provide a cloth covering.
A regular bra is designed to be comfortable for the long haul. But be cautious, some are designed to be projecting or making the breasts more pronounced. I find the very few Playtex bras I have to be like that. Comfortable, (remember the 18 hours sloagan?), so I wear under only certain shirts that it isn't noticed. Vanity Fair 76380 is one of my favorites. Super comfortable, tall sides, generous cups that are on the smaller side so they pull in well and don't push you outward. Great for long time wearing. Kohls has some on sale on the website for $13 right now. You can't go wrong witha 76380 (or the 76080, the minimizer version). Soma and VF 76380 are my favorites and what I wear all the time.