I think it's perfectly fine to like something in theory, admire it on others, but not wear it myself. For me, button-downs fall into that category, along with 3"+ heels, mid-calf skirts, pointy toes, and statement necklaces. I suppose, if I really cared, I could try to find versions that would work, but the effort doesn't seem worth it when there are so many items that I can wear without any hassle. Fashion ought to be fun, not a source of frustration.

I like crisp button downs, but soft, drapey ones are a lot easier to wear. So many good points in this thread!

Rachy, you almost made me roll out of bed laughing

Button downs are tricky for me too! As an apple with a nursing bust, I need a more feminine cut and material. I find that I have better luck with silky (but not shiny satin) button downs that have a soft drape. The stiff cotton tomboy style button downs look too masculine on me. For example, compare the two shirts below. The first one is more flowy and a better color for me and the undone buttons at the top create a V neck. The second one is too stiff and boyish on me (I should have known better than to get something called "Boy shirt") and the buttoned up collar, lack of darts and pastel blue color aren't helping--I loved the seahorse print, but I do realize I look dorky in this, so I'm returning it. I have the feeling that a tomboy rectangle like Angie or Suz et al would look great in this type of shirt though.

The first one is from The Shirt by Rochelle Behrens (Sona's suggestion)--they have an extra hidden row of buttons on the inside placket which helps prevent gaping bust--you may want to check out their site. You can also check out my recent thread with two weeks of outfits--I wore several other button down shirts: a couple short sleeve ones in white and red with feminine cuts/details, and another silky turquoise one, and a stiffer denim one but used it as a blazer over a T shirt.

I agree with the others that you have to get the right button down to match your body and style. Don't give up yet if you want one!

Rachy--LOL!

I am pear shaped with small bust and find button-downs really tricky. Especially, if I tuck, they never stay tucked. always shifting around and driving me crazy. This problem of course, only happens with cotton ones.