Put on your regular training bra, and put on a shirt over it. Look in a mirror. If you feel that your breasts are not supported enough, or look pointy and ungainly, it may be time for a cup bra.
Move around with your training bra. If it feels like your breasts are moving all over the place in an uncomfortable or painful in any way, it may be time for a cup bra.
Ask your mother, older sister, older relative, or any trusted female friend what she thinks about it. If she thinks you should buy a new cup bra, ask her to take you shopping. You probably don't need a fancy bra like from Victoria's Secret for your first bra; perhaps try Aerie, or even Macy's or discount stores like TJMaxx and Kohl's.
Get a fitting. If you go to a Macy's or Aerie, find a salesperson and ask her to measure you. She'll tell you your bra size--it will be a number followed by a letter, such as 28A, 32B, 34D, 32C, etc. Pick out some different brands and styles of this size.
Go into the dressing room and try the bras on. If your breasts do not fill out the bra, and there's a gap between the cup of the bra and the top of your chest, it's too big. If all the bras are too big, find a smaller cup size. The smallest is AAA. If that size is too big for you, you can stick with a training bra for now!
Try on a bunch of different bras. Move around in them. Wiggle--do your breasts feel supported? Try on a shirt on top of the bra--does it look smooth and natural? Once you find some bras you like--congratulations! Finding a good bra is not always so easy!
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