How to Wear a Dress Shirt with Jeans

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From a young age, most of us are told that we should never judge a book by its cover, meaning we should not base our opinion on someone by their outward appearance. But when you do not have enough time to fully get to know someone, what else are we supposed to base our opinion on?

Making a good first impression is key, and while a fair amount of charm and charisma certainly cannot hurt, you should also pay attention to how you look. Dressing for success is a good rule of thumb to follow, but that does not mean you have to walk around in a suit and tie whenever you go out.

There are a few perfectly acceptable substitutes, each of which has the potential to make a good, long-lasting first impression. The best part about these outfits is that they are fundamentally simple – anyone can pull them off, and most people will probably have access to the basic components already.

Before we get started, the important thing to remember is that you should wear your outfits with confidence. It does not matter what particular brand your jeans are or whether or not your shirt is 100% cotton. As long as you inhabit your clothes with certainty and assuredness, you will always look your best.

Before You Get Dressed…

It should come as no surprise that the particular outfit we are going to be examining in this article consists of a simple dress shirt and a pair of jeans. We will be going over the different ways to wear them later on, but for now, all you need to focus on is making sure that you have these basic pieces of apparel and that they are clean and well-ironed.

A creased shirt is never a pretty sight, and most people will notice it immediately. Your jeans are no different. Before you get dressed for the day, make sure that whatever you want to wear is wrinkle-free and spotless.

Choosing a Style

The “dress shirt and jeans” combination fits squarely into the category of “business casual” or “formal casual”, which makes it a perfect outfit for pretty much any occasion. However, the particular way in which you assemble this outfit and the way you choose to wear it can create a variety of different effects.

You should decide on this style before-hand. Ask yourself how you want people to perceive you (without becoming too self-conscious). Do you want to appear relaxed and laid-back? Or do you want something that is just a little bit more sophisticated?

Thanks to this particular outfit’s simplicity, it has the potential to become anything you want it to be if you have the right eye for fashion and what looks good. And if you do not, do not worry because we have assembled a list of different styles to try out with your dress shirt and jeans.

Different Ways to Wear a Dress Shirt and Jeans

Here you will find a description of a few of the different ways to wear a dress shirt and jeans. And although these outfits are reliable, experimentation can always lead you into promising new directions – try out different combinations and see what works.

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Dark Shirt and White/Light-Wash Denim

This is an easy outfit that not only looks classy but is also very comfortable to wear. The simple pairing of black and white is always reliable, and this dress shirt and jeans combination capitalizes on that to great effect.

There is not a lot to the assembly of this outfit. Simply throw your shirt and jeans on, and you are almost good to go. We have a few suggestions, however, that will surely help in personalizing the outfit to your liking.

  • Add a burst of color by wearing some cool red sneakers.
  • Alternatively, if you want to keep things more professional, pair your outfit with some black shoes (dress shoes will do) and a watch.

Light Shirt with Black/Dark-Wash Denim

This next outfit is the exact opposite of our previous one despite still being nearly identical in composition. A light shirt with some black jeans can make for a cool, suave look, which is perfect for a night on the town. The same suggestions for our previous outfit still apply here, although we would recommend some brown dress shoes to go with your black jeans.

T-Shirt Combo

If you want something that seems effortlessly cool while still remaining supremely casual, throw on a t-shirt to wear underneath your dress shirt, which should be unbuttoned for this outfit. We recommend finding some nice faded, slightly ripped jeans to go along with your t-shirt and a pair of white high-top sneakers for the full “Marty McFly-esque” effect – after all, the 80s never go out of fashion. Do not be afraid to roll up your sleeves while you are at it too.

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Tucked Shirt

On the other end of the spectrum, compared to our previous suggestion, if you want something that seems a little bit more put-together and professional, you should tuck your shirt in and wear a belt along with your best pair of shoes. This outfit is perfect for first dates or having dinner with friends at a restaurant, where it is still important to look great while remaining comfortable in your own skin – erm, shirt.

If you are feeling particularly fancy, consider throwing a tie on too.


Now you know how to wear a dress shirt with jeans. As we have said before, do not be afraid to experiment with different combinations. You will be surprised at the sheer variety of different effects the simple combination of a dress shirt and jeans can have.

And if you are struggling to come up with anything, you can always refer back to this article. Remember to always dress for success and remain confident in what you wear – you will always make an excellent first, second, and third impression so long as your “cool” factor radiates from within yourself.

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