Untucked Shirts for Men – A Essential Casual Shirt Guide

untucked shirts for men

Looking your best is important, and it doesn’t have to be at the expense of comfort and relaxing a bit. But untucked shirts for men can often look disheveled or careless. Depending on the setting, it may even come across disrespectful. But maybe tucking in all the time isn’t for you. Nor does it have to be.

We hear you and have your solution.

Below we’ve broken down ways to wear your shirt untucked, dressed up or down, without looking like you don’t care. You do care, and so do we, which is why you need to read this guideline. The rules are straightforward, but their importance cannot be emphasized enough.


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Casual Button Down Shirts Untucked

The Rules to Untucked Shirts

There are some key rules that must be followed to pull off the untucked shirt without looking sloppy and unkept. While not much can beat a sharp suit, there are exceptions when a shift down from formal wear is your goal. Thankfully, today’s culture favors a more smart-casual look while still maintaining respect and attractiveness.

Untucked Shirt Fit

Length, and fit in general, will make or break your untucked shirt.

While it’s important that your tucked in shirt isn’t too billowy, many styling sins can be hidden by tucking a shirt in. Yet at the end of a long day, freeing your shirt may feel great; but the wrinkles, improper length, and more will be glaringly apparent.

So to start, most important of these is the length of untucked shirts for men. How long should an untucked shirt be? That depends completely on the man and his personal measurements. When trying on a shirt with the intention of wearing it untucked, it should cover your belt, but still leave a bit of your back pockets visible.


Other fitting elements to consider next is to look for a shirt that is a slim fit but not tight. Also, check your shoulders. The seam should stop just at the point where your shoulders drop down. This is important to note with an untucked shirt because you won’t have the tension from being tucked in to pull the seams to this destination.

Lastly, but no less important, shirts with straight hems are easy to wear untucked, like a polo. It’s the varying hems (like dress shirts with tails) where it can get trickier.

Lucky for you, there are companies dedicated to alleviating this problem with untucked shirts for men. The most prominent one being UNTUCKit. The hems are not completely straight, but are significantly less wavering than a traditional dress shirt.

Other highly recommended brands to try for an attractive untucked shirt are Proper Cloth and Perry Ellis. It’s worth digging into these and other brands as many will provide custom fittings to guarantee the shirt you get hits all the right, body fitting notes.

How to Wear an Untucked Shirt

Untucked styled shirts come in all forms and can be worn in a variety of ways. Think of your untucked shirt as your style passport. It can take you from your job worn under a sweater, drinks with friends with the sleeves rolled up, or with a blazer for weekend brunch.

Untucked shirts, whether it’s a button down or a tee shirt, need to be in your wardrobe. Wearing a shirt this way is versatile and adds many more options to your outfit possibilities when professionally formal isn’t necessary or you just need a change of pace.

Other Guidelines to Consider

You now know you can wear a button down untucked, but what about adding a tie? We’ve certainly boasted about the potential the untucked shirt presents – however – wearing a tie with your shirt untucked is not an option.

If your shirt works untucked and you want to nudge closer to the casual side after stepping out of your business formal office, by all means, untuck your shirt. But your tie must be removed as well.

Lastly, when should a shirt be tucked or untucked? Or maybe the better question is: when can you get away with not tucking in your shirt? Again, thankfully with today’s ever progressive stance on style choices and a push from old conformity, untucked shirts for men work more often than not.

Of course, use discernment here, as we can’t know every possible environment in which you’ll find yourself. Respect the space and dress accordingly.

Untucked Dress Shirts

Let’s get a little more specific. An untucked dress shirt doesn’t mean you’ve taken formality completely off the table. Quite the contrary.

Wearing a well-fitting button down, untucked, in a formal setting can work. Think along the lines of weddings and networking events. While a proper fit will elevate your untucked button down, layering will take it a step further. For example: wearing an untucked white dress shirt, following the above guideline on length and fit, can look especially attractive under a cool navy dress coat.

You can even wear a suit with an untucked shirt. But you must do so very well. A dress shirt with a long tail will not work. In fact, no part of the shirt should stick out below the bottom hem of the jacket. And to reiterate, leave the tie at home.

If you want to flirt with formal and casual, combining a dress shirt with jeans, tucked or untucked, is always encouraged. But we say try it untucked if you haven’t yet. Look to the style guide and recommended brands above if you’re just getting started. Pair the untucked dress shirt and jeans duo with a sharp sports coat and you’ve got a great night out or weekend ensemble.

Casual Untucked Shirt Styling

This may seem too obvious to warrant its own section, but just because something is casual, doesn’t mean it can’t still be done wrong.

Casual Button Down


Consider first, the casual button down shirt, untucked. This will be your plaids, flannels, denims, and snap buttons. The fit and hem line rules apply here as well. A poor-fitting button down, however casual it may be, will take you from an effortlessly casual look to juvenile very quickly.

Likewise with short sleeve untucked shirts for men.

With a Jacket

untucked shirt jacket

An untucked shirt with jacket has been covered regarding a dress coat or blazer, but the same premise applies with a casual untucked shirt and your casual jacket. Whether it’s a moto style leather, denim, field jacket, or otherwise, the shirt should never hang below the bottom of the jacket.

Casual can go from composed to clumsy very quickly. Keeping those simple guidelines in mind will ensure you’re never guilty of the latter. Composure is handsome and a look every man can pull off.


Calvin Klein Men's Liquid Touch Polo Solid with UV-Protection, Cadet Navy, Large

Untucked polo shirts are more common these days than tucked polo shirts…unless you’re on the golf course or literally playing polo. But these shirts still need to be styled with consideration.

It’s the perfect option for those in-between occasions that don’t require a button up, but you need something more than a plain tee shirt. That’s why it’s important to wear one that looks as good as it feels.

Rugby shirts – the not too distant cousin of the polo – is an easy one. They are always untucked.

With a Vest

A vest with an untucked shirt is acceptable. But if you’re noticing a pattern so far in fit, it very much applies to wearing an untucked shirt with a vest.

The reason fit is especially important here is because if the vest or shirt (or worse, both) have any fitting issues, the whole look goes awry. If your vest is fitted but you’re wearing a billowing button down underneath, the tighter vest will make you look like you’re wearing an outer corset. Not the look any man is wanting to achieve.

Or if you have a well fitting shirt but the vest is too boxy or long, it completely diminishes the styling of the shirt underneath and again, will present a juvenile appearance.

Final Thoughts

To tuck or not to tuck? Untucked shirts for men is a go. But within reason.

When the worlds of function and form meet…

When clothes fit properly…

And when you can confidently go into your closet and grab nearly endless combinations of garments because there are nearly endless ways to wear them, you’ve hit the style jackpot. Being able to wear shirts untucked can be the final key to unlocking this potential. And that is something every man wants from his wardrobe.

Maximum style. Minimal effort.

Remember, when you try on shirts for the first time with the intention that they’re to be worn untucked, take the time to triple check how they fit. Here’s a refresher:

  • Simple hem line
  • Shoulder seams stopping just where your shoulder drops
  • And most importantly, proper length below your belt but not totally covering your pack pockets

Once you’ve checked off those three criteria, you’re ready to wear your shirt untucked in confidence knowing you’re doing it just right.


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