BAND MEASUREMENT (the number)
Most men measure their ribcage under their breasts to get their band measurement. Double check this measurement by wrapping a tape measure snugly around your back, under your arms and across the top of your chest above your breasts. Because your ribcage expands and contracts as you breathe, taking both measurements will help you find your most comfortable fit.
CUP MEASUREMENT (the letter)
With your bra on, wrap a measuring tape around your back and across the fullest part of your breast. Don't pull too tight! To find your cup size, subtract your band measurement from this measurement.
If the difference is...
1 inch, you're an A cup
2 inches, a B cup
3 inches, a C cup
4 inches, a D cup
5 inches, a DD cup
6 inches, a DDD cup
So if your cup measurement is 39 inches and your band size is 36 inches, the 3 inch difference makes you a 36C.
If you are not sure about measuring yourself, you can have a professional fitting at an intimate apparel shop or in the lingerie department of a department store.
Your mileage may vary, but I have been fitted for bras in both girl mode and boy mode in both venues and have never been turned away. In fact, the women performing the fittings were very helpful and seemed pleased to have a male join their bra-wearing sorority.
If you are unsure about which bra-selling venue to seek out for a fitting, you can always call ahead and ask. Also, during the holiday season, guys shopping for intimate apparel gifts is common, so walking into a lingerie shop in boy mode is not that unusual this time of year.
May you have a good fitting and buy a bra to die for!
Actor Gene/Jean Malin femulating in the 1933 film Arizona to Broadway.
Wearing Giorgio Armani.