How to Wear a Dress Shirt with Jeans in 2020

You might think that throwing on a dress shirt is a simple and foolproof way to instantly look put together, and it can be. That is, if you know what you're doing. But I'm pretty sure you don't, because you're reading this article. :-D

Maybe you've tried wearing a dress shirt with jeans and you just didn't feel comfortable. Maybe something about it looked out of place on you. Maybe you thought you looked totally awesome, until your friends started picking on you about your new look.

man wearing blue sporty blazer with belt and jeans

The truth is anyone can pull off this look with some basic knowledge about what pieces go best together, and how to style a shirt depending on the overall look you are going for. Read on for some tips on how to wear a dress shirt with jeans to ensure you look good while you're doing it.

Consider the Cut

Any item of clothing looks so much better when it is tailored to fit properly. This is especially true for formal clothing. The last thing you want to do is wear a baggy, shapeless dress shirt when you are pairing it with already casual jeans. It will just look sloppy, and you'd really be better off wearing a t-shirt.

man wearing white fitted shirt and jeans with bag

The key to pulling off the dress shirt with jeans look is to balance casual with formal.

An easy way to achieve this balance is by making sure the dress shirt you want to wear fits correctly. Many of us aren't used to the idea of taking our clothes to be professionally tailored.

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, go larger and have it tailored for a custom fit.

Pick a Pair

There is a little more wiggle room as far as the cut of your jeans goes. You can wear most types of jeans with a dress shirt as long as you remember to balance your proportions.

dress shirts for men white shirts for men mens formal shirts

You don't want to wear an ultra-fitted dress shirt with a really baggy pair of jeans, or a baggy dress shirt with tight jeans. However, wearing a baggy top with a baggy bottom will make you look like you're drowning in the clothes. If your shirt and pants are both too tight, you will look pinched and uncomfortable.

If you're going to wear a baggier pair of jeans, your dress shirt should have a more relaxed, yet still tailored cut, so you look a bit more dressed up without your dress shirt looking out of place. A tight pair of jeans calls for a more tightly fitted shirt, so you don't look like a kid who borrowed his dad's shirt for an interview. A regular fitted pair of jeans will look best when worn with a dress shirt in a medium cut.

If you always take a moment to consider the balance of the proportions of your jeans and dress shirt before getting dressed, you're guaranteed to look good. And with just a few more tips, you'll be looking great.

Style Your Look

Small details can make a big difference, especially if you want to look natural wearing a dress shirt with jeans. Styling your look is all about how you wear an item of clothing. For dress shirts, that includes wearing them tucked or untucked, rolling the sleeves up or leaving them down, and choosing how many buttons to fasten. Again, there are some basic guidelines that will help you decide how to style your shirts to achieve the best look.

man tucking in his shirt on jeans

Tucking your shirt in will always look more formal. A tucked shirt looks best with medium to tight fitting jeans. Shirts with more length in the torso will help your shirt stay tucked.

A fitted shirt will look nicer when tucked in than a baggier one, so there isn't a bunch of fabric blousing over the top of your jeans. A tucked in shirt should always be buttoned, either all the way, or with just a couple buttons left open at the top.

If you are going for more of a casual look, leaving your shirt untucked can look cool. If you are wearing baggier 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.

You can leave your shirt unbuttoned, with a fitted t-shirt or an undershirt underneath, or button it up. If you choose to button your untucked shirt, leaving a few buttons open at the top tends to look more natural with a casual style than buttoning all the way up to the collar.

man with tucked out shirt walking wearing shades

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.

For a formal, tucked in shirt, make sure your cuffs are buttoned when your sleeves are rolled down. If you want to roll your sleeves up, roll them neatly, starting at the wrist. Roll in even sections that are the width of the cuff, up to just below your elbow.

If you are going for casual, try leaving the buttons of your cuffs unfastened when they are rolled down. This style looks particularly good with baggier jeans, especially if your jeans are ripped.

If you roll your sleeves up, they don't have to be as neat with a casual look. Pull unbuttoned cuffs up to cover the elbows, then roll the material on your forearms a few times until it is just below your elbows. The cuff will stick out a bit for a relaxed vibe.

Materials Matter

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 are after. Dressier materials include silk, polyester, and cotton. Casual materials are fabrics like linen, chambray, and flannel.

chambray fabric dress shirt in 2020

Wearing a dress shirt with jeans can look better if you understand which materials go better with certain types of jeans. Casual materials will go together better with more relaxed fitting jeans, and jeans that are ripped or heavily distressed. Formal materials look sleek with solid, fitted jeans.

If the material of your shirt tends to wrinkle easily, it will be more suitable for a casual look. When wearing a dress shirt with jeans for a formal setting, make sure your shirt is ironed.

man ironing his checkered dress shirt

There are a lot dress shirts nowadays made of polyester/cotton blends that don't require ironing. Just make sure that you remember to take them out of the dryer while they are slightly damp and hang them up to prevent wrinkles.

Colors That Compliment

At this point in your life, I'm sure you have a vague idea of what colors go together. The most important thing about colors isn't matching them to each other, though. You want to wear colors that compliment you.

man standing in the street wearing dress shirt and jeans

An easy way to figure out your best colors is to take a look at the clothes you tend to wear the most. Is there a color you feel your best in? Maybe most of the shirts in your closet are the same shade, or are different colors in a similar tone. This is a good place to start.

To help you figure out if a new color will look right on you, the major thing to consider is your skin tone. Fairer complexions often look best is jewel and pastel tones, which can be thought of as winter and spring colors, respectively. Darker and olive complexions pull off brights and autumnal, or summer and fall, colors beautifully.

Don't forget that your shirt isn't the only place for a pop of color. Jeans come in all different washes and colored denim, so you can mix things up if wearing a dress shirt with jeans becomes your signature look.

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 listed throughout this article.

Layered Looks

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. Again, you want to make sure the layers balance with the entire outfit so the pieces look like they belong together.

man sitting on barrier wearing pastel shirt with blazer and jeans

Blazers can really make you look dressed up when paired with more formal jeans. You'll want to tuck in your shirt if you choose to top it with a blazer.

Sweaters can look formal with a tucked dress shirt, or a bit more casual with an untucked shirt. You can try out different sweater necklines, like v-neck or crew, and decide what you like best. Make sure you choose a dress shirt with a closely fitted cut so there aren't a bunch of lumps and bumps visible under your sweater.

Cardigans can look casual or put together. You'll want to play around with buttoning the cardigan, or leaving it open. An alternative to a cardigan is a zip-up hoodie. This can be a really cool look if styled properly.

man wearing blue cardigan and jeans

Vests come in many different styles. and if you're into them, here's one you might not have thought of trying: A suit vest. Blazers have been popular to add to a dress shirt with jeans for awhile now, but this piece of the suit offers a refreshing twist on the formal look.

For underneath a dress shirt, an undershirt can provide extra comfort and coverage. You should always wear an undershirt in a similar tone beneath light colored and sheer dress shirts, especially if you won't be adding a top layer, for a cleaner look.

Accessories

man taking a selfie wearing cardigan with necktie and jeans

The neat thing about wearing a dress shirt with jeans is that is allows you to sport accessories you'd normally only bust out when wearing a full suit. Try out neckties, bow ties, and suspenders. Experiment with different belts and styles of shoes. Have fun and be adventurous, but don't wear anything that makes you feel awkward.

Final Takeaways

Anyone can pull off the look of a dress shirt with jeans. You can, too. Just remember to balance proportions, style your clothes and choose fabrics according to the look you are going for, wear colors that look good on you, and have your clothes tailored, if needed. Lookin' good! As you get more comfortable, add layers and accessories for a look that's all your own.

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