There are serious mixed messages in our society, specifically related to the female bust. While the rate of augmentations would suggest that larger breasts are becoming more common, the fashion industry does not seem to care! As a size 6, 5'5'', 34D/DD, professional female, I have spent hours trying to find clothes, work clothes in particular, that are cut to flatter my shape. With a larger chest, you risk button-gaping, too-short torso (when tucking in a shirt), and of course the cleavage issue-- none of which meet "professional" standards. Please don't get me started on suit jackets. Instead I've found a lot of things that make me look pregnant, require endless tailoring to add darts, etc. As much as I love looking good, I'm starting to settle into a boring fashion rut because I can't find anything flattering (that is also reasonably priced, pre-tailoring). Any suggestions? Thanks!
Though I only enjoy to a minor degree the frustration you've described, believe me when I say I have nothing but sympathy for you.
Well, that's not completely true.
You're 5'5", a size-6 and rock a 34D bosom -- professional clothing dilemma aside, you must know how fortunate you are that you get to look in the mirror every morning and see what most women - and men - would call the
ideal female frame.
Now before I start in on work-appropriate, heaving-rack friendly, above-the-waist wardrobe components, I first encourage you to make sure your up-top underpinnings are the correct size and provide your girls with a sufficient amount of support. For those with a large C-cup and over, starting your day off with an ill-fitting bra can not only cause pain to the shoulders and lower back but more devastatingly, have you looking droopier, misshapen, dumpy, even (gasp)
heavier than you really are.
If you're not sure if you have the right bra, I'd recommend heading over to the fine department store nearest you and hit up the nice woman in the "intimates" section with the tape measure around her neck. There's no pressure to buy that $84 Aubade t-shirt bra, but remember, for you larger-chested ladies, an inexpensive, thin-strapped demi-balconette with Chantilly trim is just not in your professional future. One of the few downsides of bigger breasts is that your day-to-day bras are not going to look as cute and strip-teasey as you might like.
Please don't fight this.
Once you've locked-and-loaded the girls in a properly-fitting bra, let's discuss the kinds of tops you should
avoid:
Anything with an empire-waist (you'll look bosomy
and waist-less), a deep-plunge neckline (you might as well draw an arrow to your cleavage), and busy-in-front detailing (excessive ruffling, adornments, tuxedo-bibbing, or a billowy cowlneck will only add
more volume to the area you're trying not to highlight) is off-limits. Additionally, anything emblazoned with a print that's made from a delicate, gauzy fabric (think single-ply cashmere or superfine merino wool) has to be left out, for the simple reason that design-distortion almost always occurs when a big chest meets thin, stretchy fabric.
With what does that leave you? Fewer options than most but let's not forget the second most important part of this equation -- your small waist.
The problem with trapeze/empire silhouettes on a frame like yours is that the only cling that takes place is the one at your chest, leaving everything from the bottom curve of your breast downward swimming under a tent of silk, linen, cotton or whatever fabric you happen to be wearing. The taut size-6 waist you've worked so hard to achieve will look to you and those around you two-to-four sizes bigger, depending on the thinness of the rest of your limbs (I've learned the neck, ankles and wrists are the most helpful predictors of a woman's overall shape).
So yes,
once again, I advocate shirts, blouses, sweaters, shells and jackets that allow you to demonstrate in spite of your heavy chest you
don't have a heavy mid-section.
I also propose simple necklines - scoop, square, boat, Mandarin, subtle-sweetheart, etc. - and incorporating your personal flair with accents farther away from your chest, an effect that can be achieved with a showpiece sleeve (think flutter, cap, tiered, or pouf) or unique hemline (think scalloped, piped or contrast-colored). I know the button-up shirt is every large-chested girl's worst enemy, but your only choices with this style are to either swear them off entirely or do as you mentioned in your question and visit your friendly tailor after purchasing the size that fits snugly, yet
keyhole-free, across your girls. When it comes to button-ups - and for the most part, suit jackets as well - with proportions like yours, my dear, tailoring is the
only option for a proper drape.
My last two cents are to go neutral up top (nothing says "look at me
here!" like a bright color or wild print) and always opt for a slim, lower-rise fit from the waist-down. Were I you, I'd altogether avoid the wide-legged trousers, lampshade-shaped A-line skirts and high-waisted
anything, because even if you stepped out at 5'9" in a pair of
ASJINE wishlist 4-inchers, a large chest and a wide leg - and likewise, a large chest and a waistline hiked up to the ribcage - do not a size-6 look.
The proof is in the pudding.
Here below are a few styles - a starting point, mind you, not an exhaustive list - I hope will satisfy both your inclination toward professional modesty and your desire not to look like the middle-aged secretary who gave up her quest to find a heavy-chest-flattering wardrobe two decades ago.
Enjoy.

Ania blouse by Antonio Melani ($128 at
dillards.com)

Center-button blouse by United Bamboo ($166 at
activeendeavors.com)*
Silk puff-sleeve top by August ($58 at
macys.com)

Frilly sleeve top by Sara Berman ($119.90 at
nordstrom.com)

Silk charmeuse wrap-top by BCBG Max Azria ($178 at
nordstrom.com)
*I love this blouse, but I would recommend you try to find something with a more severe, less gradual shoulder-to-waist taper (remember, these are starting points!)