I'm an IT, medium busty, apple belly, and petite at 5'0, age 48. I agree that dresses can be a challenge to find. For years and years, I gave up entirely, then I started having more luck and now I have enough dresses I could go for weeks wearing a different one every day. (I haven't actually counted!)
The trick is finding your brands, and then the most flattering styles within that brand for you. The majority of my dresses are from AT / LOFT -- but that doesn't mean just any AT dress will work. Second most popular label in my dress closet is Ralph Lauren. The rest is a smattering of all sorts of brands, including Theory, Laundry, etc, etc. I own one or two BR sweater dresses but otherwise I rarely have luck with dresses at BR.
Styles that I look for include:
1. Sleeveless, or elbow length. Short sleeves cut into my upper arms and also make my shoulders look too wide.
2. No spaghetti straps
3. Scoop or V neck or draped neck (because I have a short neck)
4. Empire waist CAN work -- provided it is cut full enough in the bust, and not too full in the hips (i.e., maternity tent)
5. Ruching is my best friend -- hides belly bulges.
6. Jersey is my friend -- stretchy, forgiving, comfortable, and easy to pack, travel & wear. RL makes some of the best jersey dresses ever. I have stocked up in a variety of colors.
I have this one in two different colors:
http://shop.nordstrom.com/s/la.....ss/3713360
This one in black, and just ordered it in green:
http://www1.macys.com/shop/pro.....eath-dress
Seriously... cannot say enough good things about these RL jeresey dresses... RL understands a woman's body... I also have RL sweater dresses.
7. A line shift dresses & waist surrendering styles -- provided they are cut just so.
8. Colorblocking can do magic.
9. No inset waistbands -- my waist is too wide for them, and they rarely hit at my natural waist. A belted style can be okay, if the belt can be moved up. (My waist is fairly high up).
10. If it fits on top but is too wide in the hips, it's pretty easy to have a tailor narrow the bottom half.