Chabad Shlucha:
“Sechel youre addressing from your perspective and circles and I’m addressing from the discussions I’ve heard between my father and brothers who were in Yeshiva and my husband and brother in law who is a shliach in Yeshiva… There is that way of thinking or all bochurim would just tuck in.”
I’m not saying that all older Bochurim tuck in, many in fact don’t. What I’m saying is that most younger Bochurim don’t tuck in because they simply don’t care that much about their appearance. I used to only tuck in once a week – on Fridays during Mivtzoim. Now, I try to usually be tucked in whenever I go down the street, or outside of my dorm. I recall from my days in Zal (Yeshiva Gedolah, 17-20) we would laugh at the older Bochurim who were learning Smicha who were more often than not tucked in. Until I got to that stage myself, and began tucking in more frequently too.
Certain Mashpiim always are untucked and unkempt, that is not at all B’shittah, rather they are the kinds of people to whom Gashmiyus simply doesn’t matter, and they’re completely oblivious to it.
Regarding ties, no self respecting Bochur would ever wear a tie, save for 2 occasions, at a wedding (of a sibling) or while on Merkos Shlichus, and even then it’s not as frequent as in past years. Shluchim will almost always wear a tie on Shabbos, and many during the week as well.
I can count on one hand the amount of times I wore a tie during the past year, once at a wedding, another time on Pesach when making a Seder in a remote community.