wilked said:
There are a few easy ways to split this crowd I would say:
1. The 'fad' of untucked shirts is generally a terrible one - true/false
2. Wearing shorts after the sun has gone down is generally a bad idea - true/false
3. Wearing a jersey / sports gear when not attending a sports event should be avoided - true/false
4. The most expensive clothing you are wearing at any given time should generally be your shoes - true/false
5. If forced to choose one, it's better to have clothes a little too tight then a little too loose - true/false
Time to flip to the answer page
I'll take them one at a time.
1. True
Reading the responses above I can see people are still fairly uncertain at best, and in some cases headed off in the wrong direction. Shirts tucked into jeans look fine, so long as it's nice jeans and a nice shirt. Untucked can work fine as well given the right shirt. Untucked often looks bad as most shirts are not the right shirt.
Good visual here
http://ummybc37801t5svh193x86sb.wpengine.netdna-cdn.com/wp-content/uploads/2016/02/Dress-shirt-untucked.jpg
And an example of doing it correctly
https://static1.squarespace.com/static/55bd8090e4b002b451c33600/t/56f85b12b6aa60a67ed01754/1459116835934/
Tucked in shows you give a damn about your looks, are not sloppy, and also gives the chance to show off a nice belt. I go either way depending on the shirt, but generally prefer the tucked in look.
That said, the above images might not be enough for you, so here's a simple rule of thumb:
1. Tuck shirt in.
2. Reach up and touch the sky, high as you can
3. Can you see your belly? Shirt is too short
4. Still tucked in? Best to leave it tucked in
5. Did most of the shirt come untucked? Let it stay untucked
I think in reality tucked gets a bad rep mainly due to badly dressed men who tuck in the wrong shirt in the wrong pants (I saw Seinfeld mentioned earlier. Another example here
http://46fjj12eeht73lsxezcqpvlt-wpengine.netdna-ssl.com/wp-content/uploads/2015/03/romneydadjeans.jpg ). Those look bad tucked or untucked - it doesn't matter.
Bottom line, stick to the rules above and you'll be fine, so long as you aren't rocking dad jeans or dad shirts.