Following the Mad Men to Casualization blog post, I have been thinking a lot about dress codes and to what extent the casualization has slid.
I'm mulling over a couple of examples of "breaking" a perceived dress code, and trying to analyze why I feel like doing so is okay in certain situations and unacceptable in others:

1. Standing in line at a suburban grocery store, noting that at least half of the grown women are wearing very baggy, ill-fitting sweatpants or knit tracksuits.

2. Attending a dance ball where the dress code typically veers between formal and semi-formal. Men typically wear kilts and tux jackets; some men wear nice pants and button-down shirts. Most grown women wear ball gowns or long satin skirts, though some (like me, especially those of us on the younger side) wore cocktail length dresses. Many crafty women sew their own dresses, and look fabulous. I've even worn a knit dress in a previous year - accessorized in a more semi-formal way.
This year, several college age participants attended, some of whom dressed semi-formally, but a couple literally wore jeans and tee shirts.

3. A church that I attended while I was in college included a great range of ages - a large group of college students, and a large group of senior citizens. For the most part, many of the older members of the congregation did dress up, and many of us who were younger did as well - though some attended every week in jeans, sneakers, and tee shirts. The official church dress code was to "come as you are", but there were some in the community who felt that "dressing your best" was important. (I usually wore my version of a "college smart casual" outfit - cord pants, dress pants, or a skirt, and a top that wasn't a tee shirt.)

I felt that #1 and #2 were inappropriate. There isn't a dress code in a grocery store, but I actually felt kind of bothered that the majority of shoppers looked like they had rolled right out of bed. I'm not sure exactly why I felt bothered by it, though. Maybe it's because dressing in loungewear *was* the norm.
In situation #2, I felt a bit offended at the jeans and tee shirts, because I thought the dance being marketed as a "ball" made it pretty clear that it was a very dressy event. Then I realized that it was likely that these folks were first-time attendees, and felt bad that apparently no one had warned them to dress up a bit. How embarrassing.

In situation #3, I thought it was pretty clear that it was okay to either dress up or not, and wasn't at all bothered by those who chose to wear jeans and tee shirts even though I usually dressed up a bit more, but I know there were some in the congregation who thought it was a bit offensive to dress ultra-casually to go to church.

When do you think it's acceptable (or unacceptable) to break the norm for a dress code? Does it ever irritate you when people do so in certain situations - or am I being too judgmental?