When your primary objective in dressing yourself is to make your body look as unlike your body as possible, shit gets complicated in a right hurry. I could write entire books about the process, but I settled for a webcomic (as I am wont to do). First, you start with the chest binder, which is a garment used to conceal those unwanted boobs. Many trans men use Ace bandages to flatten their breasts, but that can cause a lot of problems, because it shoves all the fat directly onto your stomach and eventually causes loose skin all over your torso. Looking like a Shar Pei isn't an appealing prospect to me, so I go with a good old-fashioned sports bra. If you're not terribly sporty or bra-y, you might be surprised to find out that they have more utility than preventing black eyes, but what breasted people have always known is that the right sports bra can turn Christina Hendricks into Justin Bieber.
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And can turn Justin Bieber into an attractive stock photo model.
Next comes the "packy," or prosthetic penis, which is absolutely a real thing. Many of us like to wear them because it feels right, so packies are often entirely cosmetic. But sometimes, they function more or less like a real penis, with apparatuses for urinating and even inserts to simulate an erection. Technology these days is wonderful. I just got one of these dealies, which is exciting. Possibly the best part is that it's called a Pee-Cock. I wish I could have been present at the meeting of whoever made that decision, if only so I could shake their hands.