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OT , not trying to make anybody mad. BUT....

Tucked or untucked, the OP lost me at $90 for a shirt.

I haven't found a dress shirt that is a better buy than the $17 Kirklands non-iron shirts from Costco. I don't think it's completely accurate to call them iron-free, but they iron much easier than most dress shirts. If I only had to wear a dress shirt once in a while, I might be inclined to spend $90 on one, but I wear them every day so I have a closet full of them. At $17 per, I don't get bent out of shape if I get mustard or Sharpie marker on one.

As for shirts made to be worn untucked, they've been around a while:
sopranos2.jpg
 
Yeah not sure how a post about how to dress appropriately would include a mention of wearing sweatpants and a t-shirt on an airplane. I saw Jesse Palmer on a flight in shorts, a popped collar and flip flops once and thought he looked like a slob.
Damn. That sounds like me on flight to Cleveland from Columbia a few years ago; shorts, t-shirt, Wayfarer II's and flipflops (hey, I'm a South Carolinian by the grace of God!).

Took off in early March when it was around 75 degrees in Cola. Land in Cleveland and its clowdy, snowing, Lake Erie is still frozen and eveybody else on the flight gotta kick outta laughing at/with me! FTR, I did have appropriate clothing in my suitcase, just didn't leave Cola in jeans, long sleeve shirt and a jacket when it in the mid 70's outside!!
 
I look good in a smmedium ;) .

working from home = gym shorts, t-shirt (socks/slippers when it's cold out.
Travel attire = Jeans or Kahki, collared golf shirt. Cross country red eye = sweat pants t shirt sunglasses
*Bose noise canceling headphones
unless an attractive lady is interested in making small talk*
business attire/appointments =
slacks & pressed dress shirt (rarely a tie).

Just be cause you add a sport coat, doing so with out a tie seems silly to me but the business culture has popularized this look as to say, I am dressy, but cool because I don't have tie. If your wearing a sport coat or suit coat, put on the damn tie.

By the same token, you look ridiculous if you wear a tie without sport coat or suit coat.
 
I wore sweat pants on a date once. Guess you could say it wasn't received too well.
 
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If the flight is long enough the rules go away. In 2003 on a 12 hour flight to Ireland I had sleeping pant PJs on
WTH did you fly to Ireland from, Cali???

Just curious. Grandparents used to fly go Belfast from New York via Charlotte. Think it was a 6 hour flight max back then. Just sayin, just curious. No biggy.
 
I actually really like the untuckit shrts. Jeans and an untuckit shirt and I can take my wifeout to eat just about anywhere in Charleston. Regular dress shirts left untucked look very sloppy, and a dress shirt tucked in jeans looks like nerdy Dad attire. I'm 43 so i'm no spring chicken, or trend setter, I just like to look nice while remaining comfortable.
People today are just very sloppy dressers and they look like they just got out bed and put on the first thing they picked up. These days people that dress nice standout to me since so few care how they look.
 
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Tucked or untucked, the OP lost me at $90 for a shirt.

I haven't found a dress shirt that is a better buy than the $17 Kirklands non-iron shirts from Costco. I don't think it's completely accurate to call them iron-free, but they iron much easier than most dress shirts. If I only had to wear a dress shirt once in a while, I might be inclined to spend $90 on one, but I wear them every day so I have a closet full of them. At $17 per, I don't get bent out of shape if I get mustard or Sharpie marker on one.



As for shirts made to be worn untucked, they've been around a while:
sopranos2.jpg
$17 shirts? I bet you don't get any compliments either?
 
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Best bang for the buck on dress shirts-

Charles Tyrwhitt. Always running a 3 for $100 sale and often have a lot of sale items. High quality shirts that fit better than most anything else I've tried. I try and get 3 a couple of times a year.
 
If you spent around $90 per shirt. For a shirt that was made to be "untucked" you are not very smart. How gullible can people be? If I want an "untuckit" shirt I will untuck the shirt I have on. I'm going to start a company and call it the "inside out shirts". Shirt made to be worn inside out. Amazing......

People definitely don't dress classy like they used to.
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