January 20, 2012

I've always been really into vest and suits and the like, and I would love to start dressing more dapper however I have really, ah, big breasts. It's hard enough for me to buy women's clothes, let alone things designed for people with little to no chest. Any suggestions? Will clothes for bigger guys look too big and baggy on me? ( I am overweight, but trust me the breasts are a bigger issue) (NO PUN INTENDED)
Anonymous

Anon, I have been personally devastated by many a dapper button-up shirt that fit exquisitely but for scandalous gap in the chest, and I have yet to find anything near an adequately suited vest, yea though my lust for vests is quite unbiblical. So I feel your pain: I truly do. 

Unfortunately, my best answer is “learn to sew, or get a good tailor.”

Barring that: I’ve had some luck with the premade clothing roulette when I’ve been willing to sit with an army of sizes and styles, but even then 1) I only have about three or four truly workable shirts; 2) some of them are girly enough that outfits must be crafted around downplaying their frills; and 3) as much as I love owning dapper clothing, I loathe clothes shopping. I must exclusively shop in the women’s for this and hope-beyond-hope that the menswear styles are on sale… I have ventured many times into the men’s section but have never had any luck there with upper-body garments: YMMV. (I’ve had luck with pants, however.) 

I’ve been looking into custom-made button-ups lately; some internet-based companies specialize in them. I have queried a few companies about allowing me to have a shirt in the men’s styles. They’ve all been receptive; needless to say, however, the cost is a bit of an issue. I may make a public experiment out of ordering one. As for vests: I can wear a well-chosen vest under a blazer or jacket, with plenty of bobby-pin support. I am counseled that a men’s style vest fit for a woman, even a curvier one, is actually not hard to make, so I will likely budget that out when the time comes and solicit a fashion student of my acquaintance.

(Genderplayful, by the way, understands these problems & will hopefully provide better solutions sometime soon.) 

Best of luck to you, fellow dream-chasing crossdresser. Please feel free to tell me of any successes & failures - and send me pictures!

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