3 Easy Ways to Wear a Dress Shirt with Jeans – May, 2022

by Jamie
dress shirts (2)

A dress shirt is something that tends to be paired with formal pieces, with their slim-fit shape complementing a smart look. However, the dress shirt with jeans look is one that’s both flattering and easy to work into a range of different styles. 

Everyone knows how to wear a dress shirt with a suit, we do it most days at work or for any kind of fancy occasion. But, how to wear a dress shirt with jeans, that’s a whole different ball game. We’ll go through some of the ways you can make this combination work, focusing on things like color, pattern and fit for both your jeans and shirt.

A couple of shirts in different colors and fits are enough to cover all your needs. Every wardrobe needs at least one classic fitted white shirt as it’s is the easiest color for matching with everything. Never underestimate the power of the white dress shirt.

White Dress Shirt

You can make so many different combinations with a classic white shirt, and it’s one of those staples that you really need in your wardrobe. You can create a whole variety of looks depending on the style of jeans you go for, but if you want to create a smart casual look it’s best to go for a darker shade of denim. This mimics the look of the formal shirt and chinos combination but maintains a casual, comfortable twist.

Black Dress Shirts

Although black shirts aren’t the most common feature in menswear, their sleek look and versatility make them ideal paired with a variety of looks. Pair one with some light-toned jeans, such as grey or blue ones, for a contrasting look, or create a slick all-black look by keeping the color scheme simple and uniform.

Printed and Striped Dress Shirts

So black and white shirts are pretty standard. They tend to act as a blank slate and can be accessorized according to what kind of outfit you want to go for. Patterned shirts, on the other hand, have a little more personality and can be used to add some dimension to an outfit. If you’re working with a dress shirt and jeans look, the stripes or prints can also keep the outfit on the casual side of things, keeping the overall look less structured. 

Shirt Fit

If you want to make sure you’re getting your dress shirt and jeans combination looking the best it can then it’s important to get the fit right. If you’re wondering how to tuck your dress shirt into your jeans remember that the fit of your shirt and your jeans is equally important to pull off the look. If your jeans are wide fit or your shirt has a pleated edge, then it’s best not to tuck your shirt in, as, in simple terms, it just won’t look good. 


The proportion of your shirt can alter your look, helping to emphasize certain aspects of your body for better or worse. First off is the length of your shirt. If your shirt hangs too low on your jeans it’s automatically going to make your legs look shorter. This isn’t really a problem for tall

This isn’t really a problem for tall guys and is one of the reasons they can pull off the longline look, but if you’re a little shorter than average, or you just want to appear taller, then it’s best to keep your shirt no longer than your hip bone.

A shirt that’s too short isn’t going to work well either, but we feel the reason behind that is pretty self-explanatory. A belly top as a shirt is never a good look.

How to Tuck in a Shirt

Knowing how to tuck a shirt is a gentleman’s essential, and let’s face it, we’ve all wondered “how do I tuck my dress shirt into my jeans?”. Now, we know this sounds like a dumb thing to focus on, and something that’s pretty simple, but even seemingly standard tasks can be done incorrectly. If you’re tucking in your shirt, especially if it’s a little long, then you need to do it in a way that doesn’t accentuate the excess material.

Jeans Fit

There are many different jeans that fit to pick from, ensuring that you can find a fit that works best for you. Not everyone is going to be able to pull off the skinny jeans looks, and some people will prefer the equally striking wide fit jeans instead. The good thing about shirts, however, is that they tend to look good with any style of jeans you go for, so you can stick to flattering cuts while wearing your favorite shirt. Just please, for the love of all things holy, avoid the bootcut, for all our sakes.

If you don’t have the time or energy to try out different shapes of jeans to see what suits you best, then just go for a pair of slim-fit jeans. They’re close enough to help define your legs, but not so tight that they’ll accentuate any excess bulk or scrawny limbs. You’ll also be able to have your shirt tucked or untucked depending on your preference, so they’re a practical, versatile option.

How to Wear Dress Shirts with Jeans

  • A plain white shirt can be mixed with different tones of denim to create a variety of vibes. The darker the denim the more formal the look.
  • Patterned shirts help to add some more personality and a casual twist to an outfit.
  • The fit of your shirt is important, so make sure you’re working with a shape that flatters your body.

On That Note

The classic humble dress shirt has had a style upgrade this season, and after reading this guide you should be all clued up. Jeans will forever be an essential piece alongside the dress shirt so it would seem silly to not combine the two, right? Just follow the steps we have outlined above and you’ll be the chicest man in the office this Friday.

Feature image from Pinterest

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