Should You Tuck In Your Polo Shirt?

The other night, my wife and I went out to dinner with a couple other relatives.

My in-laws graciously watched our boys so we could have a nice date-night (something for which I am always grateful).

As always, I gave my outfit considerable thought.

We were going out to dinner and drinks, so I wanted to get dressed up a bit (obviously), but the venue we were going to was rather casual. We were actually all on a bit of a vacation at the time, so the restaurant/bar we went to had a breezy, beachy vibe to it. My wife was also getting dressed up, so I wanted to show her proper respect and match her level of formality.

To give you an idea of the formality of the place, it would not have been out-of-place had I worn shorts and a t-shirt. It was the kind of place where you’re not sure if your drink will come in an actual glass or a plastic cup.

Clearly, I wasn’t going to wear a t-shirt. But I had to decide how to get “dressed up” without looking too formal AND without being too hot, as there was a chance of us sitting outside.

I decided to wear chinos, boat shoes, and a polo shirt underneath a navy blazer (with no pocket square).

The blazer was from Suit Supply and is unlined and VERY light. So light I can see through it when I hold it up to the light. It’s my go-to warm weather jacket for that reason. It also has little-to-no shoulder padding and patch pockets, which further casualize it.

As you can see, my polo shirt was navy-and-white striped.

Overall, I felt that the outfit was very nautical and felt appropriately “beachy”, especially since I went sans socks. I also felt it was the right level of “dressed up”, even though I was the only guy in the restaurant wearing a jacket.

One of the more important decisions I had to make regarding my outfit was whether or not to tuck in my polo shirt.

To tuck a polo shirt, or not? It’s a debate that is always raging on internet menswear sites.

Honestly, men tend to make polos more complicated than they really are. People think they’ll look like dorky middle-managers or State Farm employees. In reality, polos are one of the easiest ways to upgrade your style and they rarely look bad, provided you choose one of actual cotton, and not one of those weird, synthetic golf shirts.

Wear a polo shirt in almost any instance you would wear a t-shirt. The magic is that it will always look more elevated simply because it has a collar. It really couldn’t be any easier!

Yup, a polo shirt is pretty hard to mess up.

Even though a polo shirt is considered casual (“elevated” casual, sure, but still casual), are there times it should be tucked in? Like in a business casual environment or when wearing a jacket over it?

Good questions!

It’s my opinion that a polo shirt should be left untucked. I know we can all find pictures on the internet of men looking great in tucked-in polos, but as a general rule, I tend to go with NOT tucking in my polo shirt.

Now, why, as someone who usually advocates tucking, am I instructing you to not tuck in your polo shirt?

Well, for three reasons.

Reason number one is that the hem of a polo shirt is usually flat. Yes, I know that it often has a “polo hem” which means the back of the shirt is a little longer than the front, but the hem itself is still flat all the way around. This indicates to me that the shirt should be left untucked, since it doesn’t have the curved “shirt-tail” hem of a regular dress shirt.

Reason number two deals with the fabric of the shirt and its properties. Have you even tucked in a polo shirt? Tucking it in stretches out the fabric in a really strange way. Regular dress shirts don’t do that because they are woven and not knit, like polo shirts. A woven shirt is a bit more rigid and doesn’t stretch the way a knit shirt does. So, if you tuck in a polo shirt, you’ll find it becomes loose and baggy all over, which just means you need to tuck it in even further throughout the night to keep the visible part of your shirt from looking too slouchy.

Reason number three is that polo shirts are supposed to be casual, knockaround sportswear. They’re made for playing tennis and golf. They’re not meant to be passed off as “formal” so if you try to dress it up too much it will look weird and a bit dorky.

But I wore a jacket that night. Shouldn’t a shirt worn under a jacket be tucked in?

Yes, 99% of the time. Except when that shirt is a polo shirt.

Honestly, I am not a fan of wearing jackets over polo shirts because of the tucking problem and because the collar of the polo shirt tends to collapse under the collar of the jacket. The polo I wore that night is actually pretty substantial, so it held up fairly well, but most of the time the collar of a polo will sink down under the jacket and look bad.

So why-oh-why did I decide to wear that particular outfit?!

Well, like I said, I wanted to wear a jacket but I also didn’t want to be too “dressed up”. It’s a hard balance to find and I usually advocate just diving in and being dressed up. But my outfit was actually right on the money. I could have worn a proper shirt and tucked it in (and it probably would have looked better), but then I would have wanted to wear socks and actual real shoes (not boat shoes). That was more formal than I felt was appropriate for the venue and the company.

That then begs the question… should I have not worn the jacket? Is the jacket the problematic element in this outfit?

Possibly. Wearing a jacket over an untucked polo shirt kind of enhances the mid-section (which wouldn’t have happened had I worn a shirt that I tucked in). However, I am glad I wore the jacket since our table at the restaurant was directly under a very strong fan. It felt amazing, but the addition of the jacket ensured I was comfortable the whole night.

Holy smokes… a lot to consider for a night out!

In conclusion, don’t overthink the simple polo shirt. It’s supposed to be easy and casual. If you tuck it in, you risk looking a little too fussy. Just leave it untucked.

If you feel like where you are going requires a tucked-in shirt, then don’t go with a polo shirt. Go with an oxford-cloth, button-down shirt or something like that.

Not tucking your polos is actually really helpful for guys just getting started in menswear. If you mentally categorize polos as “casual, no-tuck” then you’re much more likely to wear them in casual settings where you might have just worn a t-shirt in the past. Wearing a polo shirt instead of a t-shirt is one of the easiest and quickest style upgrades you can make, so thinking of them as “on par” with t-shirts will help them effortlessly slide into your existing wardrobe.  

But… maybe don’t wear a jacket over it.