I was wondering the SD opinion on wearing, say, a golf (ie polo) shirt. Do you tuck in the shirt tails, or go untucked? Personally, I like it hanging out, but do most consider this “sloppy”? Personally, I think people have way too much time on their hands if this irks them! (Call it "irkenomics, huh?) 
At work: tucked anywhere else: untucked
I concur.
ETA: Age might matter a bit with this. I’m 27.
Also, if the shirt-tail is short enough and you will be active enough so as to have it untucking itself along the course of the day, better leave it out to begin with. Or admit you need one size larger 
Agreed.
The only exception I make is if the shirt tail is freakishly long for some reason. I have a couple Penguin and Ben Sherman shirts like this that I only wear tucked in.
Business casual means they should be tucked in. If it’s not business casual, then it’s you prerogative.
I agree with this sentiment. I would only add that, in my humble opinion, tucked in polos look geeky on almost everyone. So if you do need to do business casual, wear a button front shirt.
If you’re wearing a polo untucked, make sure it’s not blousey and definitely not stretched out. That’s what makes it look sloppy. Even if you’re over weight, don’t wear a shirt that’s too big because it looks worse.
It’s fine to wear it either way, but tucking does look a little nicer or more formal. I wear button-downs much more than polos, and I’ll even tuck or untuck as the day goes on if I want to look more formal in class than I do playing frisbee afterward.
Usually I tuck a shirt in.
I don’t think it looks geeky (but hey, I’m a geek for a living and I wear 'em that way), however I do agree that how good it’ll look depends on your bodily proportions; if your shoulders are broader than your waist it looks much better tucked than if you have a large stomach - 40lbs ago I looked overstuffed if I tucked in my shirt, it calls attention to a big stomach. Now that I’ve lost the weight and several shirt sizes I find that I have to look for shirts with a “fitted” cut (less baggy arms and more taper from shoulders to waist). They look good untucked as well because they don’t bag out at the hem.
If you’re going native, out. Civilized, in.
I’ve always tended to tuck mine in, even if it’s a polo-type shirt, or one of those Gap or Banana Republic type t-shirts meant to be worn as outerwear. It’s just my preference. The only time I think anyone looks particularly sloppy if they don’t tuck their shirt in is when they wear a jacket or sweater over it, and the shirt tails hang out visibly underneath. I tend to put on a sweater quite often (and just as often take it off, to maintain the truth-value of SweatersWorn==1).
These things come and go with the generations. I brought up this subject in an earlier thread, and most respondents in my age ranged seemed to prefer going untucked, and to have preferred it in the past. But I’m not sure I buy it. Until about 1990, a trimmer, more fitted look for men was the norm, and tucking your shirt in was a part of that. From about seventh grade on (late 1969 for me), most young guys I saw around school, and generally, tucked their shirts in.
Still, if you’re into the oversized jeans look, then you probably look better with your shirt untucked.
Just IMO, of course.
It depends on how the hem of the shirt is cut. The “penguin tails” referred to above are intended to be worn tucked in. The extra length is to prevent the shirt tail from being pulled out when the wearer leans forward. Polo shirts with square cut hems can be worn tucked in or not…if there’s a slight V notch at either side, they’re intended to be worn over the trouser waist band. Dress shirts should never be worn untucked, except by young ladies who are mostly undressed. At one time it was possible to buy shirt garters that attached to the tops of your dress socks. This kept the dress shirts neatly tucked in, and the socks from falling down around your ankles. I never wore them myself, but I knew a man who did.
Long sleve shirts it’s simple. Dress shirts like you would wear with a suit, always tucked. Casual long sleve shirts like you would buy at Express or The Gap, always untucked (you can tell by the squarish shirt tail). An untucked dress shirt makes you look like you are a rebellious prep schooler, came from a fraternity coctail party or are a businessman on a bender (or like you just fucked one of those people and are wearing his shirt).
Polos are pretty much whatever. I say tucked in with dress pants or chinos or untucked with jeans.
The problem with polo shirts, is that depending on your physique and how you wear them, they make you look like:
-a homosexual fitness trainer
-you work in Best Buy
-an IT dork
-an excessively preppy douchebag
-you are going golfing
Unless you’re actually exerting yourself (working) then tuck the damn thing in you lazy slob. If you’re doing something where you would constantly have to retuck (golfing, chasing your kids, whatever), then just leave it be.
I, too, am a fan of the shirt garters. Except mine don’t clip to my socks. I prefer the ones that have stirrups that you slip your feet into. I guarantee you will not have to repeatedly tuck your shirt in all day. Though you may feel like you’re strapped in all day long. For me, it is a posture reminder. If I don’t have a bit of tension on them, I know I’m slouching.
I wear mine untucked, and my partner wears his tucked. But he’s skinny and I’m not, and I think that makes a big difference.
Maybe I’m just being young and sloppy, but I like guys who keep things untucked. An untucked dress shirt can be sexy. But to me, a tucked in shirt says nothing more to me than “I’m going to work.”
And tucked in polos? Really? I can think of few things less attractive.
Once when wearing a tucked polo in the Blockbuster store, a couple of people asked me if I worked there. No doubt they thought I must be an employee, but I was wearing jeans too, and not the khaki pants worn by the real employees. That might be one of the reasons I don’t like polo shirts any more, but it’s definitely not the only one.
I still just about always tuck it in. In the course of the day I’m sure to put a sweater or jacket over everything, and I hate the look of an untucked shirt-tail peeping out from under the jacket. That’s when I feel like a slob, much more than just wearing an untucked shirt over some jeans.
Shirts are determined by the cut of the hem…if they are ‘straight’ cut they are worn out, but if they have a curve on the hem, they are worn tucked into the trousers…according to my BLOKE who knows things all blokey.
