Slight update from yesterday: after speaking with a Rabbi/Doctor teacher of mine, the family medical history issue, while warranting further explanation, should not be a deal breaker of any sort. It seems I was fairly on target with the way I handled the news and how I considered it after the fact. One point he and discussed was that everyone (literally) has some sort of health issue in their family, and in this case, knowing what it is ahead of time can actually be very beneficial. With proper care of one's health, screening, and general alertness, the worst can be avoided. Additionally, it's much better to know what to expect rather than be caught off guard by a surprise that may only manifest itself at a later stage of development, when prognosis is much worse. So thank you, Rabbi/Doctor teacher!
Back on topic: Black hats. I figure I haven't been living up to the fullest intent of this blog by not commenting on a grey area in hashkafa recently, so I owed y'all one.
Hats have become a "thing" in more yeshivish/right wing circles. The wearing of fedoras (I am not going to discuss the furry headwares of the Chassidim) has become almost a uniform of sorts; an open declaration of what hashkafa you espouse. At least when you attend a right-wing Charedi yeshiva, or live in certain cities/neighborhoods (such as a certain city in New Jersey).
But hats have even become pervasive in the more modern community (the in betweeners, I guess) who, although hashkafically may be within the YU-realm, lean to the right (as an aside, don't we lean to the left at the Seder on Pesach to avoid choking? Just kidding). Typically, hat wearers also feature a velvet kipa, but I've also seen suede kipot with hats, and even a few kipa sruga/Borcelino combinations (and by kipa sruga I mean the white variety, I would say the black sruga are basically equivalent to suede), which really leave me discombobulated. That sort of seems like a case of tartei d'sasrei or something... but then again pulling elements from the far left and far right and blending them together sounds like a nice recipe for reaching a balanced central position.
I happen to wear a hat on Shabbos and Yom Tov, at weddings and (lo aleinu) funerals when I am "on the job" as a member of the Chevra Kadisha (I feel another post brewing). I've gotten a bit of flack in the past about not being consistent about the hat wearing, since most typical yeshiva bochurim wear them all the time for davening, no matter what day of the week. I'm not sure why I made that initial decision... perhaps it was part of my developing grey ideology wherein I was a wannabe yeshiva bochur, but never quite felt to the level to wear white shirts on weekdays (that's also a whole different discussion). I also wear the hat on chol hamoed, due to the yom-tov-ish status of those intermediate days, but only during Mincha/Ma'ariv and not Shacharis (and subsequently Mussaf) because I find the tefillin/black hat juggling act to be a pain in the neck - literally. The hat is so precariously balanced on the very back on the cranium, and you basically have to lean your neck inward while keeping your head up to keep it from falling. The end result? A visit to the chiropractor.
I remember a very memorable night dvar Torah/mussar schmooze given by Rav Cohen, a Rosh Yeshiva at YU, last year during on of the Friday night onegs. Rav Cohen himself is one of the more charedi Roshei Yeshiva at YU, and is known for his fiery, enthusiastic mussar - a real kick in the pants delivery (which I find we all need a bit of every now and then). I've always been a big fan of his, if one can say that about a Rosh Yeshiva, but he became an even bigger favorite after I heard this speech.
During the course of an enthusiastic talk about Shabbos observance, he randomly brought up the subject of guys who only wear hats on Shabbos, and the other yeshiva guys who make fun of them for specifically the point I mentioned - either wear it or don't, enough with the half-and-half business. Rav Cohen rebuked the critique-ers! He said that those who wear a hat on Shabbos and not during the week have it exactly right. Shabbos, he said, is a time that deserves our attention in various ways, which certainly includes upgrading our dress to reflect the increase in holiness inherent in the day. The yeshiva bochurim who wear white shirts, suits, and hat during the week have basically no recourse for "dressing up" for the Shabbos. A tie doesn't count, as insignificant a garment as it is, and certainly not in comparison to someone who dons a suit specifically for Shabbos.
Hats are the same thing. Someone who wears a hat only on Shabbos is doing so with the right kavana in mind, he's accentuating his attire for the sake of the holy Shabbos. Shabbos is important enough to him that he has a specific garment designated to enhance his appearance l'kavod Shabbos.
That certainly beat my old answer I'd use to give for wearing a hat - that I was an Indiana Jones fan... I do think I'm a bit old fashioned, taking into account the fedora and double-breasted suit, which I've been told is entirely out of style many times over. Add that to my trench coat, and I look like something out of the 40's, which would fit the Dr. Jones timeline quite nicely.
Anyway, I find Rav Cohen's perspective most agreeable. While I am not in any way endorsing the need to wear hats, and consider it more of a personal/fashion choice, I like the idea of the fedora having more meaning behind it than simply - "look, I'm part of the club too" because that makes them seem like those Mousketeer hats. Everything in life should be done with intent, not mindlessly because it's the "in thing" to do. I guess that's the bottom line in this post.