You can definitely wear any kind of shirt – casual or dress shirt with jeans – what is important is how you chose your dress shirt and jeans and style your shirt with your jeans. The key to pulling off the dress shirt with jeans look is to balance casual with formal. And that can be done in various ways. Fit of the shirt and jeans Jeans with dress shirt should be well tailored and well fitted ones – generally straight fit, slim fit, skinny fit, bell bottoms go well with dress shirts – but if you prefer comfort or baggy jeans that’s ok as well provided you balance it with the right fitting shirt. Many of us aren't used to the idea of taking our clothes to be professionally tailored. Made to measure tailored dress and jeans

If you have some shirts, you really like, but their fit is off, either overall or in a certain area, take them to a tailor to have them fitted properly. When shopping for dress shirts, look for fitted or modern cuts that don't have a bunch of extra fabric. If you are in between on sizes, have it tailored for a custom fit.

The last thing you want to do is wear a baggy, shapeless dress shirt when you are pairing it with jeans which by its inherent nature is a casual wear. Also you cannot wear a super fitted shirt with a really baggy jeans or a baggy shirt with skinny jeans – at the same time a baggy shirt with a baggy jeans will also be too much to handle. If your shirt and jeans are both too tight, you will look uncomfortable.  So if you want to wear a comfort jeans – your dress shirt should also be a relaxed one but still tailored cut so look dress up and a tight pair of jeans will got well with a slim cut shirt. A regular fitted pair of jeans will look best when worn with a dress shirt in a medium cut. So if you just look for a good balance you are guaranteed to look great. A good fitting is the key  Any clothing looks great when it is tailored to fit perfectly. Wearing a well fitted shirt with a custom tailored jeans jeans cut to your measurements will always look great. Especially when it comes to formal clothing – fitting is the key and for that it is always recommended to go for custom tailor-made clothing.   Styling Small details can make a big difference, especially if you want to match a dress shirt with jeans. Things to decide whether they should be tucked or untucked – sleeves rolled up or down, all of this depends on what kind of look you want.
  1. Tucking your shirt in will always look more formal. A tucked shirt looks best with medium to tight fitting jeans. Also a fitted shirt is better when tucked to give it a more formal look. Shirts with more length in the torso will help your shirt stay tucked. A tucked in shirt should always be buttoned, either all the way, or with just a couple buttons left open at the top.
  2. If you are going for more of a casual look, leave your shirt untucked can look cool. If you are wearing baggy jeans, an untucked dress shirt is the way to go. A medium fitted jean also pairs well with an un-tucked dress shirt. The bottom hem of the dress shirt can be shorter, and it should be nicely tailored so it still looks neat, even though it is un-tucked.
  3. Fabric - Wearing a dress shirt with jeans can look better if you understand which materials go better with certain types of jeans. Be observant about the material your dress shirt is made of to help you decide if it is the right shirt for the look you want. Dressier materials include silk, polyester, and cotton. Casual materials are fabrics like linen, chambray, and flannel. When wearing a dress shirt with jeans for a formal setting, make sure your shirt is ironed. But in general a good quality shirt is must if you want a formal look.
  4. Roll your sleeves - You can roll your sleeves or leave them down for any look, but there are subtle ways to make the sleeves work better depending on how formal or casual you want your style to be.
  5. Color - It's always a safe bet to wear darker colors for formal outfits and lighter colors for casual outfits. This isn't a hard and fast rule, though, especially if you've followed the other guidelines. Don't forget that your shirt isn't the only place for a pop of color. Jeans come in different washes and then there are colored denim, so you can mix things up if wearing a dress shirt with jeans becomes your signature look.
  6. Layering - For even more versatility, and warmth if you're dealing with a cold climate, layers can really elevate a simple dress shirt with jeans get up. Make sure the layer you are adding doesn’t look out of place. Jackets can really make you look dressed up, sweaters or cardigans can look formal too.  Play around with buttoning the cardigan, or leaving it open.
Anyone can pull off the look of a dress shirt with jeans. All you need is to just manage the balance, styling, fit, color and fabric according to the look you prefer. Adding layers such as a jacket can just elevate the look of a dress shirt. What is important is to understand the look you want to create by wearing a dress shirt with your jeans, ensuring the shirt is well fitted and and the jeans are tailored to fit you and the most important of them all – feel confident in what you wear and you will always be in a safe zone.