Another Disco question

I've spoken before how I've become a pretty huge fan of Chris Disco Hayes. Recently he was promoted from AA NW Arkansas to AAA Omaha. I've since written in to ask him a question, which I'll post here:

How old is too old to wear your hat backwards? I've heard that the general consensus is 27 yrs old. But I've also heard that trucker hats with velcro or snaps can be alloted an age much younger than that. Likewise, flex-fits can be worn backwards past 27 but there's just an overall confusion on the entire matter. Please clarify for the masses before the hysteria consumes us all.

Aaron D.
Kansas City, MO

Aaron, Aaron, Aaron. I'm willing to bet you're 28 and still trying to pull off those dorky trucker hats with white mesh and random logos that sit like five feet up off your head aren't you? Just kidding. :) It's a good thing you asked this question when I was responding because unless Disco was a fashionista (last time I checked I'm pretty sure Disco only had tapered jeans and old man sweaters hanging in his closet before he met me), I doubt he'd be able to give you any kind of sound and up-to-date fashion advice.How old is too old to wear your hat backwards? I'm pretty sure if you're not younger than 9 years old, you're too old to wear it backwards (unless of course you're a catcher) (or a ridiculously hot guy with a chiseled face and a little bit of scruff) (or my husband in the off-season when he's allowed to have any facial hair). Well, my hypothesis failed me. My plan was to show you pictures of the hottest of the hot guys out there who pull off backwards caps like exotic dancers pull off their clothes, but I've found my hypothesis to be invalid. It seems all the hotty-hot-hots are so hot they don't ever go out with a backwards hat, let alone any kind of disguise covering their gorgeous faces. For instance, I scoured the internet and didn't find any of these gems with a backwards cap of any kind.
So if you're average looking without amazing hair and impeccable looks like the fellas pictured above (Utley, Hayes, Beckham, Hayes), you can wear a hat at any age. And if for some reason you're blessed enough with a movie star face, you can wear whatever you want, whenever you want. Got that? Man, I'm getting myself all worked up over here with all these hotties, two of them being my ridiculously good looking husband, I've lost my thought process. Where was I?Ah. fitted hats. Yea, you know, I guess you can wear them as long as they aren't too tight so they don't leave a ring around your head. I actually like guys in ball caps, so disregard everything I said above and dress up your head to your hearts desire. (Random side note: A while back before I met Disco, I threw a "Dress Your Head" party... you basically had to do something fun from the neck up. We had everything from pink wigs, to chicken hats, to one guy wearing ah sock. Yea, 'parently he didn't get the memo.)Back to being serious for a second. Anyone can pull off pretty much anything if they're confident. Confidence rises above all trends of what to and what not to wear. If you're trying to pull off a rad Hurley trucker hat as long as you carry yourself with confidence (not cockiness, which is easily discoverable) you're going to look great. Just one cardinal rule, unrelated to hats. Whatever you do, if you're under the age of 55, please do NOT be seen in public wearing socks with your sandals. Capeche?