Re whether the pocket polos are good or bad: That depends on your mindset; is looking like Ned Flanders a good thing or a bad thing? (Although they never show it, you just know there’s a pocket polo under those crew-necked sweaters).
When I am off work or not in social situations/events where business casual or formal wear is required, I sometimes will leave shirts untucked in summers as a way to cool down and not “overheat”.
In summers, tucked in shirts tend to cause me to heat up more quickly which isn’t good. Especially considering I’d rather be too cold than too hot.
It’s also a way to signal that I’m in casual “relaxation mode” without going all out and wearing a Hawaiian style type floral shirt.
FYI - those are not “Hawaiian style type floral shirts”. They are aloha shirts. B-) And they are business casual to semi-formal wear:
For men’s dress shirts, “athletic” is different from “slim”, and “athletic” is much less common.
http://www.brooksbrothers.com/bb-size-guide-men/bb-size-guide-men,default,pg.html indicates that 18" neck assumes 50" chest and 46" waist in Brooks Brothers men’s dress shirts. The 4" drop (chest minus waist) is the “portly” sizing; “regular” is 6" and “athletic” is 8".
MRE, my DH will only wear polos with pockets. Every suit is navy or gray. Khakis are always pleated. He’s a big guy and doesn’t care at all about fashion, with the exception of french cuff shirts and cufflinks when he meets with the Fed or international colleagues.
My sons will only wear jeans that are on sale. I had to buy S1 jeans last winter because the ones he took to college in 2008 had finally worn through (and yes, he wore them to work).
If you’re new to the untucked thing for button-down shirts, a general rule of thumb is not to wear it untucked it if it’s really long. If it’s hanging well below your behind when untucked, it’s probably too big or just not appropriate for wearing untucked. Deep tails for example, are meant to be tucked. Shirts with shallow tails can be worn untucked. Shirts with no tails are designed to be untucked. You also probably don’t want to wear very loose-fitting shirts untucked in general.
I always tuck for work; I almost never tuck outside of work. And I never tuck when wearing jeans. If I need to tuck for a more dressy restaurant, I definitely won’t be wearing jeans.
I live on the West coast so things are a bit more casual out here. I suspect my style wouldn’t fit in as well in the mid-West or East coast. But at the end of the day the only opinion that matters is yours. Wear whatever is comfortable for you in the manner that makes you comfortable.
In Hawaii.
Doubt the above argument would fly in much more stuffy East coast corporate environments though it would be nice if I can get away with it. 
I am not talking about NYC corporate, cobrat. B-)
Fashion is definitely regional thing. H wants to retire to the South so that he can wear a seersucker suit in the summer. I’m not sure you can get away with that outside of Charleston.
OP,
Here’s one suggested talking point with your wife:
She’s very fortunate you haven’t resorted to the fashion choice of wearing a chicken suit…
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But I like cargo pants, I can carry lots of stuff in all the pockets. No manpurse for me!
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But doesn’t all that stuff make you look lumpy?
Why not just carry a manly looking messenger bag? Both of my kids carry professional looking messenger bags…tablets, etc, are protected and easily carried. H still carries a briefcase, but maybe I should get him a messenger bag.
Oh gosh, younger son is obsessed with cargo pants. Claims he could travel around the world with a couple of pairs of cargos and a small bag.
He also loves cargo shorts.
There is no hope for the men in my family. 
In contrast our son won’t wear shorts that he deems “too cargo-y”
Definitely a messenger bag, @mom2collegekids!
Messenger bag? No way. The goal is to not have to carry anything in my hands. I rarely carry more than a wallet, keys, and phone. And cargo pants are actually a lot better for a phone, no risk of sitting on it.
That Brooks Brothers chart is interesting. According to it, I have an XXL collar, an XL chest, and M-L waist. Where can I buy that shirt?
I’m wearing white socks today, with my faded jeans and white sneakers. Another fashion crime to add to my rap sheet.
^^
please link to a pic or change your avatar.
^ What, you doubt that a person could be such couture crime scene?
I wear cargo pants when I’m flying. Everything goes into the pockets - kindle, boarding pass, wallet, keys, cellphone, earbuds, reading glasses. Only thing I have to carry in my hands is a sammich and bottle of water.
DH worse seersucker in the northeast. And in CA. Down south, you may like the option of the hat to go with it.
I don’t have the problem with white socks that I have with seeing pants legs so short that they show any color socks. (Or so long that they drag and fray.)
Can’t you just get those large dress shirts tailored? A pain, but it would polish. Not so expensive, considering.
Add me as a no to messenger bags (except on or around campus.) Ever look and see what they do at the shoulder of a nice suit or blazer? Cargo pants, to me, are what they are. Same with photog vests or some (even high end) travel vests. I’d prefer seeing that to a fanny pack (which I think is ridiculous.)
I realize that fashions come and go, but I haven’t figured out why wearing white sneakers/running shoes suddenly became such a horrible crime. White or predominantly white tennis shoes are simple and basic, which is usually the sign of something that is always acceptable. And IMO they look a lot better than a lot of the over-the-top sneaker styles you see screaming at you from the sports store displays today - silver running shoes with day-glow orange trim and bright blue laces, for example. Styles like that are going to look ridiculously dated in just a very few years. That style will be dead long before the shoes themselves wear out.