12 Ways To Style a Button Down Shirt

Everyone is familiar with the button down shirt. It’s been a staple in men's clothing for ages. 

Some people wear them every day for work. Suit and tie guys are well-acquainted with the button down shirt. Other people may only reach for their button downs if they’re attending a wedding. These guys probably feel more comfortable in t-shirts. 

Regardless of how often you wear a button down shirt, it’s worth considering the different ways you can style them. Knowing the variety of ways you can style a button down shirt will allow you to get multiple looks out of the same shirt. It can also make the button down more approachable for those who aren’t regular wearers of the style. 

It doesn’t have to be a stiff, uncomfortable shirt—that idea may be based on an experience with a less than ideal shirt. Button downs also don’t have to be reserved for dressing up; there are several ways you can style a button down for casual and comfortable wear. 

This style guide will cover 12 ways to wear a button down shirt.

Tucked In Button Downs

Tucking in your button down shirt is, of course, the most traditional way to wear it. However, there are ways to wear a tucked-in button down in a casual way as well. These outfit suggestions show a range of ways you wear a button down shirt tucked in. 

1. With Trousers

Tuck a button down shirt into a pair of trousers for a traditional, dapper look. You can wear this outfit in a professional or formal setting. All you need to complete it is a pair of dress shoes. A belt is a nice touch but not a deal-breaker—just make sure to match the belt to the color of your shoes if you do wear one. 

This simple shirt and pants pairing is the base for a number of traditional inspired looks. Change the outfit's vibe to something more casual by substituting dress shoes for a pair of minimalistic sneakers. Make it more formal by adding suspenders or a tie. 

2. With Jeans and a Belt

A button down paired with jeans and a belt can come across several different ways depending on the choice of shirt, jeans, and shoes you wear. 

Black or dark wash jeans will look more dressed up with a solid-colored button down and dress shoes or ankle boots. 

Light wash denim with a button down will look more rugged and casual but can be trickier to pull off. Be selective with the shoes you wear. Sleek brown leather shoes or boots will go well, such as oxfords or Chelsea boots. Stay away from bulky shoes or sneakers, as this runs the risk of looking like a contractor or a dad from the 90s. 

3. Under a Jacket or Coat

Another popular way to wear a button down is under a jacket or coat. A neutral button down will take on the characteristics of the jacket you wear it with. 

For example, if you wear it with a sport coat, you will achieve a traditional tailored look. Choose your pants and shoes to match a formal look. Wingtips and slacks that compliment your coat work naturally.  

On the other hand, if you wear a versatile zip-up jacket over your button down, you’ll be sporting a modern professional look. You can wear this with Workday Pant or All Day Every Day Pant for a comfortable but sharp outfit. 

Untucked Button Downs

While the button down shirt is traditionally worn tucked in, the decline of formality in American fashion has made wearing button down shirts untucked just as acceptable. The untucked style makes button down shirts more casual and allows for many more outfit possibilities. 

One thing to note when wearing an untucked button down shirt is the style of hem. Some button down shirts have a long or scalloped hem that’s designed to be worn tucked in. Shirts with these styles may not be the best option for wearing untucked. For an untucked look, choose a button down with a straight hem that falls around the waist. 

4. With Chest Pockets

A button down with a chest pocket on each side is a detail that adds style versatility. Typical button down shirts catered for more traditional wear usually have one or zero chest pockets. Two chest pockets with button enclosures make your shirt stand out in a subtle way and will help create polished casual outfits. 

On top of the smart design, this shirt is made from a blend of materials that stretch and keep you warm without adding bulk. The technical fabric blend is enhanced with a 22% Thermolite Core for well-balanced insulation.

5. With Joggers

Wearing a button down with joggers is a trendy way to mix traditional with modern, though not every pair of joggers will rise to the occasion of pairing with a button down. You don’t want to wear a button down with joggers made entirely of cotton, for example. 

However, a pair of quality joggers made from performance materials will have a sheen and fit that creates a luxurious feel and appearance. This allows them to compliment a button down well. 

6. With Loafers

Loafers and untucked button downs are similar. An untucked button down is a laid-back interpretation of a traditional shirt, and loafers are the most laid-back of the dress shoes. It’s in the name: _loaf_ers. 

An untucked button down and pair of loafers go together to create a look that nods to formality as it deliberately bends the rules of tradition in a tastefully carefree way. Wear this combination with a pair of the comfortable All Day Every Day Pant to match the fresh, easy-going look. 

7. With Sleeves Rolled Up

Rolling up the sleeves on your button down is another way to style it casually. It’s decidedly informal while maintaining some element of traditional dress. It’s a cool way to adjust your office attire for an after-work look that you can wear to meet up with friends. 

8. With a Slick Backpack

A modern, on-the-go professional needs the option of bringing their work with them. Between remote work, video calls, commuting, and traveling, a professional backpack for all your essentials makes a huge difference in practicality and style.

The untucked button down is a look that maintains professionalism but is casual enough to rock a backpack—a professional backpack at least. 

Unbuttoned Button Downs

The unbuttoned button down is the most casual way to wear the shirt. It’s a modern interpretation of the style that’s cool and comfortable. 

9. With Shorts

The most casual look you can get out of a button down is wearing shorts with your unbuttoned shirt. This look is perfect for warm weekends and has summertime in its DNA. Pair your unbuttoned shirt with Workday Shorts to keep up with the traditional origins of your shirt or with the All Day Every Day Shorts for a fit choice that matches the laid-back, unbuttoned look. 

Wear sneakers or leather sandals to complete the look. Sunglasses will match the vibe as well.

10. With a V-Neck

A v-neck is a good choice to wear under your unbuttoned shirt because it will show off the shape of the neck and add subtle detail to your outfit. Consider matching the color of your v-neck with a pair of slim fit pants and showing contrast with the color of your button down.

For example, a dark v-neck and pants paired with a light-colored button down or vice-versa will create a contrast that allows the different elements of your outfit to stand out and, at the same time, complement one another. 

11. Color-Blocked With T-Shirt and Pants

An unbuttoned shirt obviously allows the shirt you wear underneath it to be seen. One way you can use this to your advantage when putting an outfit together is to think about the concept of color blocking. 

Color blocking is the concept of pairing two or more bold colors together to create an exciting ensemble. Traditionally it applies to bold colors, but you can work it the same with subtle colors and shades as well. 

For example, you can wear a navy button down with a white t-shirt underneath and khaki pants. The key is to keep each individual piece basic and solid in color and let the complementary colors take the lead in how your outfit pops.

Another easy color combination is to wear a light grey shirt with a dark grey t-shirt and black pants. In this case, you’re color blocking with three distinct shades, showing an entire spectrum within one cohesive outfit. 

12. With Joggers and Sneakers

Joggers and sneakers are athletic by themselves; you wear them both to exercise. However, since athleisure has become so popular, the doors have been opened to mixing athletic clothing with pieces outside of the athletic wear category. 

Wearing an unbuttoned shirt with joggers and sneakers is a perfect example of the dynamic range you can show with athleisure clothing to create a fit and professional look all in one. Choose quality joggers with a smooth finish and leather sneakers free from logos and embellishment for a clean-cut look. 

The Button Down Shirt: A Can't-Miss Classic

The button down shirt is a timeless style that can’t be replaced. It’s a staple in every man’s wardrobe. Traditional and familiar, the button down is often attributed to business or formal occasions but is not limited to a single domain. You can get several looks out of a button down shirt—and anyone can pull them off. 

Because the button down shirt has a full range of how it can be styled between casual and formal, start with the occasion you’re dressing for. If it’s a proper occasion, plan on wearing it tucked in and style accordingly with dressier choices for the rest of your outfit. If you’re dressing for a more casual occasion, consider the many ways you can style a button down shirt untucked or unbuttoned so that you look sharp but relaxed at the same time. 

Any way you style it, the button down will maintain an element of class and confidence that follows you wherever you wear it.