Collared Shirts: The Casual Way

The right shirt is the cornerstone of a man’s wardrobe. After all, men don’t have too much choice with clothing. It’s mostly a variation of shirts, pants, jackets, etc.

It’s confusing enough to work with those basics, imagine what women have to deal with…

Today we’re going to talk about collared shirts and casual ways to wear them.

Sometimes a man wants to avoid collared shirts that make him look he just got out of work, and wear them in ways that give him a laid-back aura.

Let’s get to it.

Short Sleeve Collared Shirts

Surrounded by tees and tank-tops during the warm weather, you can stand out with a bit more class and elegance by opting for a collared short sleeve instead.

A short sleeve shirt naturally brings with it a casual aura that long sleeves (even when the sleeves are rolled up) can’t match. At the same time, you keep the classic touch of a dress shirt with the collar.

Variegated Stripes

Variegated stripes are associated with nights out so they’re more appropriate for such. Try wearing this Italian-style pattern underneath a blazer or a sweater. Just be careful about wearing it without a blazer in the clubs, because you may look like a carbon copy of many guys there.

I love these shirts because the color patterns can take the place of a tie and still pack the same punch. Without the tie, you look more relaxed and ready for some fun, but the shirt still adds an accent to your outfit.

In the case that you do plan on wearing a variegated striped shirt with a tie, go with a solid tie to maintain balance.

You don’t want pattern on pattern – it’ll get too busy.


A gingham shirt is a great way to bring life to a suit. It’s also a great choice to wear on top of jeans for a casual date.

Heck, it’s a lot more interesting than the pinstriped shirt that every other guy is wearing and certainly more interesting than a blue collared shirt.

Roll up the sleeves and you’re good to go – all style, no fuss.

Military Shirt

This military-inspired shirt is seen as a more fashionable button-down. It’s perfectly casual and gives your frame some structure and strength as well.

Take it upscale with a pair of dress pants, keep it cool with a pair of broken in chinos, or rock it with your favorite pair of well-fitting jeans.

Shirts that Rock

These type of shirts make you lose all association with collared shirts and seriousness. With embroidery and art, it becomes less formal and gives the collared shirt more bite. The typical rules start to blur when you bring up the rocker archetype, so don’t hesitate to get expressive with the details.

Ways to Wear It

1. Top It Off With A Sweater

As it starts to get chilly out, you can pair a dress shirt with a cardigan or a sweater and bring it down to laid-back status.

I recommend using a colored shirt underneath instead of plain white so that you don’t look so much like a math teacher. You can also use this opportunity throw in some bold colors (such as pink, purple, lime green) to the dress shirt.

2. Are You a Tucker?

To tuck or not to tuck? That is the big question. Especially when it comes to whether or not you want your look to seem casual. 

Dress shirts are almost always made to be tucked in. The reason for this is so that when you sit down, the tail lies under your rear and it prevents it from riding up or coming untucked.

If you’re wearing a suit, for goodness sakes tuck in your dress shirt. But on a casual level, you’re either a tucker or not.

Some casual dress shirts will come in already come in a short cut and these are okay (and meant to be) to be worn outside of your pants.

I see a lot of guys on the streets doing the half-tuck. Tucking it in up front, leaving it out in the back. Try to avoid this. There are very few people who can pull it off. If you insist on leaving it out in the back, the shirt has to be short enough that you don’t have a whole bunch of fabric flying back there.

Some people may want to tuck their shirt in up front to show off a fancy belt – if your belt is that cool, you might as well tuck it in all the way.

For those who are avid untuckers, be warned that untucking your dress shirt can make you look shorter. Not to mention looking like a slob. If you’re a really short guy, you’d be better off tucking your shirt in, it’ll give the illusion that your legs are longer than they really are.

If you insist on leaving your shirt out, I suggest getting your shirt cut shorter by a tailor to look more flattering.

3. Loose Another Button

How low can you go?

Depending on how you’re feeling, at least unbutton down to the second button from the collar. I wouldn’t go any further unless you want to display that you’re ready to take it off.

4. Leave it Open

You don’t always have to button up, a button-up. Leave it open and show off a graphic tee or a low-cut undershirt.


Casual doesn’t always have to equate to a t-shirt or polo, bring in some casual collared shirts into your wardrobe so you have a lot more to work with.

Next time you’re meeting some friends straight off of work, you’ll know what to do in order to avoid looking like it ~ (while turning some heads while your at it).

And remember, whether you’re dressing up or down, a stylish man knows the ins and outs of taking any piece from his wardrobe and matching it to the occasion.

Stay sharp,


  • Style Habits says:

    Great article, but why didn’t you go into any details about different collars themselves or the different types of cuffs? Myself, I love spread collars, especially with ties, and a good french cuff is always fun.

  • Diaz says:

    Be careful when you untuck your shirt after work for the casual event, as shirts tend to get all wrinkled and it doesn’t look good if you have a nice clean ironed shirt untucked, but the lower part of it is completely wrinkled.

  • donpeppinoo says:

    That’s the basics! Every man needs a Collared Shirt without you ain’t one!
    And for gods sake tuck it in if it’s meant to!
    Most guys are running around with their collared shirt hanging over their ass. It is neither for painting nor for sleeping it should dress you so tuck it in!

    Sorry for my very bad english!

  • Yike says:

    I started wearing collared shirts open in the front with a graphic tee as a way of getting both a collar and a graphic tee for work (wearing a collared shirt was recommended). Now it’s become my favorite way to wear my graphic tees by far. What I like to do is match the main color of my collared shirt with the pattern color of the tee. Can’t really comment on the variegated stripes or the checks (never been my thing), but everything else seems spot on. Props.

  • Dan says:

    Some more tips on how to wear shirts the cool way:

    – No pocket! A pocket makes a shirt at the same time less formal AND less cool.
    – Slim fit! Nothing says “engineer at the office” like a ballooning, ill-fitting shirt
    – A cool, non-formal belt can loosen up a dress shirt a lot. Try pattern, woven, used look, contrasting colors, …
    – I’m not a big fan of leaving a dress shirt untucked. A proper shirt is meant to be worn tucked, and looks much better this way. If you want untucked, wear a polo shirt.

  • hvl says:

    Are there some collared shirts specially designed to be worn untucked or just the usual ones? Some of mine are slightly too long to be worn untucked.

  • Rahul says:

    Good article. I really like the advice this blog has to offer. Is there any particular brands or designers you would recommend for collared shirts? I usually have the bad habit of keeping collared shirts untucked and I have a little trouble maintaining the condition of the shirt. Any tips? Thanks again!

  • Brett says:

    I can’t imagine someone tucking in a collared shirt. I live near a college campus and I’ve almost never seen it done. I think it’d look a lot worse than untucked.

  • Brett says:

    Oh yeah, and untucked unbuttoned is best!

  • Marshall says:

    Good article, as I am getting more interested in dressing a lot nicer. I do have one question, and it’s one of concern: What are the rules for casual if a man has a pouch in the front? Because all the guys in these pictures are quite fit and thin.

  • chris says:

    dont like it tucked in

  • Rane says:

    I always wear collared shirts full buttoned with sweaters..its nice!

  • Jason says:

    Simply put, a shirt tail curved hem untucked looks better. There ain’t no stigma no more for untucking a shirt! Tucked is boring, an untucked curved shirt tail flatters your hips and azz. Make sure the tail doesn’t hang more than halfway down your back pockets or fly, unless you have exceptionally long legs, as you want to balance your upper and lower body and don’t let it hang past your crotch…. if its too long then take it to a tailor to get it shortened and make sure its not a potato sack with no shape around your mid section. If you’re slim then wear a slim fit shirt.

  • Henry says:

    That Short Sleeve Collared Shirt looks fantastic! I love the way the collar and the cuffs(?) are white.

    Just that little difference makes it look great. What shirt is that and where can you buy shirts like that? Anybody know any good brands?

  • Susie says:

    Great article but guys you have to be self-assured to carry off the untucked look and not look like a student (and so fairly immature) or a guy that can’t fit it round his paunch so has no option.

    Tucked is a wiser option anytime.

  • greg says:

    Tucked in allows a very cool belt to be seen

  • John Murphy says:

    Nice Article,

    Big fan of the short sleeved shirts, great looks and tuck those shirts in for sure!!

  • Martin Whysall says:

    These are the absolute wardrobe to wear at office.

  • Let us hear your thoughts when you’ll give it a try 🙂

  • Marshall,

    Honestly the best answer is “lose it”. Getting down to a slim physique is one of the best ways to make sure you always look better in clothes. I realize it’s harder for some than others, so do your best!

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