Battling the DDD in Menswear

Anonymous asked: "I am a curvy queer girl (size 16-18 US) who just came out, and I’m starting to dress with a more masculine feel. The problem is, I have DDD cup boobs- menswear looks completely weird on me, if it fits at all. Any advice for finding stuff that fits, or WHERE to find it? I thrift like crazy, which leads to some great finds, but some new stuff would be good too. Thanks!"

Hey there! Sounds like we are both fighting the battle of the boobage.
I know how hard it is to find menswear that fits a large chest. After all, most menswear wasn’t made to have room for such things, especially large ones. 

I shop at Belk almost exclusively. Their brand is Saddlebred; it’s cheap and of decent quality. Ralph Lauren shirts also fit me well (ta-da!) I haven’t had much luck with other brands off the rack. So shop around to find a brand that fits you.

If you can’t find a brand that you like, tailoring is the way to go. Buy shirts that fit you in the chest, and everything else can be tailored; sleeves, shoulders, etc.

Here is an old post with tips for Tailoring Men’s Button-ups for Larger Chests.