To tuck or not to tuck, that is the question.
But what is the answer?
Well, the answer is it depends!
Generally speaking, the length of your shirt will dictate whether or not you should be tucking it in. For example, dress shirts should ALWAYS be tucked in. In fact, one of the ways you can tell a button up shirt is a dress shirt is based on the length of the shirt. Dress shirts are purposely made longer so that when you tuck them in, they will stay put.
Casual or “sport” shirts, on the other hand, can be worn tucked or untucked depending on your preference. However, if you are planning on wearing a casual shirt untucked make sure that the bottom of the shirt isn’t too long or too short, otherwise you will end up looking like a big dork.
What about Short Sleeve button up shirts?
The same rules apply to short sleeve button up shirts as to their long sleeved brethren. Short sleeve dress shirts should ALWAYS be tucked in, while casual short sleeve shirts can be worn tucked or untucked.
What about Polo shirts?
Strictly speaking, you can tuck in a polo shirt based on the same basic principle of shirt tail length as discussed above. Additionally, I should mention that polo shirts made of a higher quality fabric (think Lacoste or Ralph Lauren) look better tucked in compared to some of the more cheaper varieties out there. Personally, I think a polo shirt tucked into a pair of shorts looks immensely more stylish than tucked into a pair of chinos but that’s just me.
Can I tuck in my T-shirt or Henley?
I’ve seen men commit this style blunder on many occasions and they need to stop. Unless your intention is to wear a t-shirt as an undershirt (we’ll have more to say on that in another article), you should never be tucking in your t-shirts. It looks plain ridiculous.
I know some of you will object to this and say, “But my t-shirt is too long and it would look strange if I didn’t tuck it in.”
That’s because you bought a t-shirt that’s too big. Buy a new one that actually fits. Problem solved.
Nothing screams “over the hill” more than when I see a man tuck in his t-shirt. It’s no wonder that this style NOPE! is most often committed by men in their 40s and above.
Don’t be one of them!
Remember that when it comes to tucking in your shirts the basic rule of thumb is to go by the length of the shirt itself. Shirts with longer tails (e.g. dress shirts) should ALWAYS be tucked in. All other shirts can be worn tucked to untucked based on preference, except for t-shirts and henleys, those should NEVER be worn tucked in unless you want to look like a putz.