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It can look sloppy, of course, but some shirts are made to be worn untucked and if it's short and neat, it can be a very cool look. Okay, sure I do notice the horribly wrinkled shirt bottom hanging out under a jacket to ones knees...
No one looks good in the clothes they were wearing 20 years ago. ...
Ah, generalities. Love it.
The last thing I'll be doing is tucking in my henley under my black (or brown) racer, either on or off the bike. Sometimes I tuck, sometimes I don't. Depends on the shirt, the pants, the shoes, the destination and my mood. In my humble opinion, if one says you must always tuck, or says you must never tuck, its rediculous, and a style disaster waiting to happen.
I think that's the problem right there!
It's not so much 'should I tuck a shirt or not with a leather jacket', but more 'tuck or not to tuck with jeans'. I never tuck with jeans, unless I am wearing wearing a jacket. But tucking with jeans can be dangerously uncool territory.
I agree with many of the comments above.
Avoiding generalities is impossible when writing relatively short comments.
As Lip says, always tuck with chinos and slacks, but jeans, not jackets, are the problem. I'm 42 years old, and most of my friends, wife's friends, and all of our associates are kind of around the same age, so whilst I might be ok doing my grungy shirt tails out of jeans thing when popping to the store, I don't want these people to see me and think I'm a bum. As I said before, now that I'm not in my 20's, I always tuck with jeans, and I agree with Nick that it is a more grown up look- more mature (and as Nick points out, 'mature' doesn't have to mean 'uncool'). It also looks less like I'm desperately trying to cling to my 20's by 'proving' I'm somekind of 'rebel' or something. After all, 20 year olds now don't dress the way I did when I was 20, so who am I kidding that I'm 'cool' with my 'devil-may-care, shirt tails out attitude'?
It does make the jacket look smarter, and make the jacket the focus.
But with jeans, I still worry that when I take the jacket off, and my flannel shirt is tucked in, that I look like my dad. I guess I just have to learn to be comfortable with middle-age.
It also looks less like I'm desperately trying to cling to my 20's by 'proving' I'm somekind of 'rebel' or something.
Live and let live. If some feel more comfortable with their shirt untucked, there is no need to suggest that they are trying to relive their youth, nor that maturity will likely change their ways. There are plenty of well-adjusted 40-50 something guys who, for any number of reasons, elect to untuck their shirts.
'Why can't it simply be a matter of what feels most comfortable?'
Because I have to worry about what other people think of me, because I care about the effect that has on my work, my wife's business, our income, our access to the good things in life that we get from having connections, and introductions.
Maybe, or perhaps the kind of people who are too lazy to tuck their shirts in, and don't care enough about how bad they look to others, are just too lazy, and don't care enough, to put up a strong case for their point of view? Maybe untucked shirts really are indicative of a lazy slob who doesn't care how bad he looks to others, because he will never value their opinions, because he's like some kind of a rebel in his own mind?
I second the observation above that those who always tuck are coming off a bit more didactic, intolerant, and generally emotionally invested in the tuck / untuck conversation, the importance of which is trivial at best.