How To Wear Dress Shirts Casually

If your occupation requires a dress code, dress shirts are going to be your bread and butter during the workweek. You’ll also bust these out for formal dinners, weddings, and other events with formal dress codes. And for many men, that is where the dress shirt’s use cases end. What a shame! Because, contrary to popular belief, you can actually pull off some stunning outfits by wearing dress shirts casually.

Wait, hold up – can you wear dress shirts casually? And if so, how do you go about pulling this look off?

It’s true. Dress shirts worn casually are actually one of our favorite looks. And fortunately for you, we’re going to talk all about wearing dress shirts casually today. We’ll teach you how to wear dress shirts casually so you can dress these down outside of work while still looking dapper. It’s really just a matter of taking a few buttons down, throwing on a different pair of pants, a jacket, and perhaps some nice sneakers. There are a few other caveats that can make or break your intended look – so you’ll want to pay attention when putting your outfits together.

Don’t worry, we’ll cover all the details for you shortly. First things first – let’s address the elephant in the room: can you wear dress shirts casually?

Can You Wear Dress Shirts Casually?

We know what you’re thinking – everything you’ve known has led you to believe that the dress shirt is meant to be worn with a nice pair of custom tailored slacks – or at least with a pair of custom made chinos. You may even be inclined to throw a tie on and tuck your shirt in every time you button up that dress shirt. So, what gives? Can you really wear a dress shirt casually? Yep! You sure can. Just as you can wear an overcoat casually or wear dress pants casually, so too can dress shirts be worn casually.

Think about it like this: while the dress shirt itself may be more of a formal garment, it is just one of the many components of your outfit. You also have to take into account your pants, shoes, and any jacket you add to the ensemble. If you keep everything else a bit more casual, it will dampen the formal look of a dress shirt.

But that’s not all. You can also tweak the manner in which you wear your dress shirt. When wearing formal shirts for formal settings, you’ll have them tucked all the way in and buttoned all the way up. You’ll probably even have a tie on. But, to make that shirt a bit more casual you can roll your sleeves up, leave the dress shirt untucked, and maybe undo the top 3-4 buttons. You can even pop the collar (not our preferred look, but to each their own!) to draw back on the formality of these shirts.

All of this is a long-winded way of saying, yes – you can wear a dress shirt casually. And we’re about to walk you through how to do just that. Let’s get started!

How To Wear Dress Shirts Casually

Pulling off the casual dress shirt look is actually not that difficult. With our guidance, you’ll be well on your way to transforming the way you wear the formal shirt. The best part? Rocking this style can be as simple as you want it to be. You can keep your entire work outfit the same – and just ditch the tie and take a few buttons down. Or, you can go back to the drawing board with an entirely different outfit.

Let’s start with some simple tips that anyone can try themselves.

Keep Things Simple By Unbuttoning The Top Buttons

If you’re in a time crunch coming from work or an important meeting and want to take things down a notch, but don’t have time for a full-blown wardrobe change, that’s ok. Even a suit can be made more casual simply by unbuttoning the top few buttons and changing your shoes. We see plenty of men wearing nice, custom-made suits make things a bit more casual by throwing on some nice sneakers, removing their tie, and taking down the top 2-3 buttons of their formal shirt.

Sure, this look isn’t quite as casual as rocking a dress shirt on top of some denim jeans. However, it definitely can dial down the look of a suit. If you’re in a bind and need to casualize your outfit fast, try this out – all you need is a spare pair of sneakers in your car or your bag!

Stick With Linen Over Cotton For A Casual Dress Shirt

This piece of advice is for those who are willing to go out and shop for a casual dress shirt. While all button-up shirts are formal to some degree, there are certain styles that lean more casual than others. In our opinion, the linen dress shirt look is quite a bit more casual than the traditional cotton formal shirt. Just by swapping out your cotton dress shirt for a linen dress shirt, you’ll make things quite a bit more casual.

Our Favorite Casual Dress Shirt Look: Pair With Denim & A Sport Coat

Now, this is the moment we’re most excited about – sharing our favorite casual dress shirt look with you. Start with a nice linen dress shirt. Then, pair it with a nice pair of custom denim jeans and a custom sport coat. Just add your favorite pair of quality sneakers, and boom – you’ve got a dapper look that will have you turning heads every time you step outside.

Of course, to really put the finishing touches on this look – drop a button or two off the top of the shirt and leave the dress shirt untucked. When done correctly, this is our favorite way to wear a dress shirt casually. You’ll still look incredibly stylish and professional – but you won’t be overdressed.

Let A Sweater Do The Talking

Want to tone down the formal shirt a bit more, but still let it add an accent to your look? Try pairing a nice custom sweater with the outfit above instead of a sports coat or blazer. With this look, wearing dress shirts casually is super simple.

With this look, you’ll only see the collar of your dress shirt pop through the sweater. You may also see the sleeves extending a bit out of your sweater. This alone is enough to catch the attention of anyone who has the pleasure of laying eyes on you. Here, though, you’ll want to keep that dress shirt tucked. But, you can uncuff your dress shirt sleeves and roll them up a bit. For best results, stick with black jeans or raw denim jeans.

Rock An Untucked Dress Shirt With The Sleeves Rolled Up

One final way you can go about wearing dress shirts casually is by simply untucking them and rolling the sleeves up – almost to your elbows. With this look, you can attain the casual vibe you’re seeking without having to add a sweater or coat – perfect for those warmer days when you still want to rock a dress shirt.

With this style, you can unbutton an extra button to really give casual energy. This will create a sort of “v-neck” appearance to your casual dress shirt look. Put some bracelets or a watch on your wrists since they’ll be exposed – this will help tie the whole look together. We love pairing this look with some nice khaki pants or custom chino trousers. Go with a dark shirt up top.

When In Doubt: Seek Out Inspiration!

You now know how to wear dress shirts casually – as we’ve shared some of our absolute favorite looks with you. But if you try these styles on and aren’t quite loving them, that’s ok. You can seek inspiration on Pinterest or other photo-sharing websites like Instagram. Your best bet is to start curating more and more style imagery in your life and start experimenting yourself to find what you like best. And if you really want help building your wardrobe out, you’re in luck. We’ve got just the thing for you – keep reading!

Final Thoughts On How to Wear Dress Shirts Casually

Well, there you have it – just about everything you need to know regarding how to wear dress shirts casually. As you now know, wearing dress shirts casually is not rocket science. Take a few buttons down, lose the tie, and leave the shirt untucked. It can be that simple. Or, build your own casual dress shirt outfits with the inspiration above.

You’ll notice a common trend throughout the tips above – we always encourage you to go custom in all your garments. There is a reason for that. If you ask most well-dressed men, they’ll tell you that what you wear and how you wear it are just two pieces of the puzzle – a third, equally important piece is how it fits. That’s why we recently wrote a complete guide on how dress shirts should fit.

Even the most well thought out, stunning outfits will miss the mark if your clothes don’t fit you perfectly. So, spend the extra money and go custom if you really care about how you look and want to put your best foot forward and make great first impressions. You can’t put a price tag on that!

And, for all your custom garment needs, stick with Black Lapel. We don’t just the best selection of custom dress shirts online – but all sorts of garments. From suits to shorts, sweaters to dress pants, and everything in between. But beyond just helping you get quality garments that fit your body, we can help you ensure your clothing fits your lifestyle. Our menswear specialists can sit down with you virtually (or in person at our Boston location!) and talk through workplace dress codes, style preferences, and more. We’ll help you build a wardrobe that excites you. Let’s get started!

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