A Shirt’s Tail

Cassie and I have this ongoing “discussion” about whether I should tuck my shirts in. Yesterday was Casual Friday, so the issue was on my mind again. Casual Friday is an institution which has been abolished and reinstated a couple of times by my company, as senior management changes, and new brooms like to attempt social engineering and put their feet down/loosen up alternately. Rather like reorganising by discipline or by market – which will it be?

It’s surprising how divisive this issue can be, and how strongly I and other people feel about it. I have some pretty firm views. I don’t want the “dress shirt, tails out, boot-cut jeans and square toe shoes” look – that reminds me too much of what we used to call “townies” in Bedford. That look reminds me of slightly older men going out on “the pull”, and I don’t identify with it or like it. The next level of that is wearing a shirt with french cuffs and cufflinks, untucked with jeans. Not my thing at all – and it surprises me that I have to explain why I find it repellent.

Sadly that image does seem to have sunk in as the cool look in certain circles. In movies and TV shows, you might have two guys – one is “uptight”, whereas the other is “cool”. The cool one has stubble, untucks his shirt, gets the ladeez, and is played by Bradley Cooper.

I did a bit of a search and found that there is a lot of discussion on the menswear and style blogs about it. In the comments I’ve read, some people say tucking in your shirt is a “Euro” affectation. Others say untucking it is a “Euro” affectation. In both these cases, I think there’s more than a touch of the good old American stereotype of the Euro-male as being at best too consicous of clothes, and at worst, a screaming bender. Racist homophobia, in other words, yay!

I wish I could say tucking in was a UK thing, or a Euro thing. But I’ve had this same ongoing discussion with girlfriends in the past in the UK. I remember one formative incident, being encouraged to go out wearing khakis and a dress shirt, untucked. It was at a party in a bar, with a karaoke competition run by a flamboyant (and bitchy) gay guy. I did a song (as did everyone else), and as I was walking off the the stage, the MC said, “Big hand for Matt there! Check him out – he’s one cool customer with his shirt out!”, or something like it. It really stung, not least because we had the shirt-in-or-out argument before we went out. I bloody knew it. Scarred for life.

Some people say that men who don’t tuck their shirts in aren’t paying attention, or they don’t care about their appearance. Many men who leave their shirts untucked say that they consciously do it so they don’t want to appear stuffy or square. But they then go on to project that belief onto everyone else, and it’s sad. Some say that tucking in is an affectation. Others say that untucking is an affectation. The word affectation has a big effect on me. I oscillate wildly between sneerily dismissing things as an affectation, and being guilty of it myself. It’s a personal foible, related to my fierce dislike of judgement, and my thorough enjoyment of judging.

This chap writes 4 reasons not to tuck in, and pretty much raises all the old ghosts about looking square and tightly wound. Let’s take them one at a time (excuse the paraquoting):

  • “Most shirts aren’t cut to flatter when tucked in” – get shirts that fit, and they will flatter.
  • “Never tuck in a t-shirt” – off the point, but I agree.
  • “Never tuck in a jersey” (by which he means a sports team top” – again, off the point, but I agree. I’d never wear a jersey anyway, ‘cos I couldn’t give two shits about sport.
  • “Never tuck in a sweater” – off the point, but I agree.

He rounds up with

It’ll convey a relaxed attitude. An effortless ease. A hipper approach to life.

…to which I’d say, “If your definition of hip is untucking your shirt and hanging around ‘pulling’ in Mick’s Tavern, then call me Peewee Herman.” I’d also take issue with the misnaming of the article. It should be “One Reason I Don’t Like Tucking In My Shirt, And Three Other Items Of Clothing You Shouldn’t Tuck In”.

But it’s the comments that really get me. There’s men and women on both sides of the argument, and some corkers, especially the ones perpetuating the old classic thing of “get with it, Grandad, only nerds tuck in”.

The same website published a rebuttal by another writer, which went some way to correcting the previous one, but said some pretty wrong things along the way – such as “always wear a belt”. He did make some good points about finding shirts that fit you. Obvious, you’d think, except that the previous article had given the fit of “most” shirts as a reason to leave them out. Then Details called untucking “jejune” and “desperate”.

For me, the question of whether a shirt should be tucked or untucked comes down to two things: opinion and rules. Of course, these two things cover pretty much every possible situation, so let’s break it down.

First off, what do we mean by “shirt”? In this case, I’m talking about “casual” shirts. But let’s look at each kind of thing that could be called a shirt and say whether it should be tucked (in my opinion, backed up by many writers on men’s fashion).

Never tuck it in.
Polo shirt (like a t-shirt with a collar and a couple of buttons)
Never tuck it in. Even when the back of it has a longer tail. It should do, because they’re designed for when you’re playing polo. Much like the chukka boot.
Dress shirt
Always tuck it in.Under a suit coat or blazer? Tuck it in, no question.
It’s worth clarifying some terms here. A “button-down” shirt is a shirt with a button-down collar. That’s the official definition anyway, and it’s telling that much of the writing that advises against tucking describes a button-down as a shirt with buttons down the front. It suggests that the dress shirt is now a special kind of shirt, rather than the default. This is a nice piece about the history of the real “button-down”.
(Of course, the other end of that is the insistence on calling shirts “shirting” and suits “suiting”, as if trying to evoke an image of your own tailor, with rolls of fabric in a rack behind him, rolling out some shirting for you and cutting it to size. After that you go to the grocery store and buy some “fooding” – perhaps some “cheesing” and “vegetabling”. To quote Count Arthur Strong, “It’s not cheap, curtainin’!”)
Casual shirt
Depends. If it has long tails, tuck it in. If it has a flat bottom, or a slight curve to the bottom, then leave it out. Shirts are made differently depending on whether they’re designed to be tucked in or not. As stated by Put This On: “…we’re generally in favor of tucking in your shirt. It’s a cleaner, sharper look that is much better suited to layering. If you do wear an untucked shirt, though, it’s important to wear one that’s cut to be left untucked.”

Of course, once again it all comes down to doing what you like, and not caring about what people think. But having my shirt tails hanging out isn’t because I’m worried about what other people think – it’s about what I think, and what kind of person I look like.

You may be observing the level of sartorial baggage I carry. “Loosening up” isn’t going to fix that. I also carry a little baggage of another kind – the kind that, if I wore my shirt untucked, would make me look like a 70’s darts player. Nuff said.