What is a Boyfriend Shirt? (How to Style It)

If you’re in love with the boyfriend shirt style style, you’re in good company. The iconic style dates back to the 1960s when none other than Marilyn Monroe sparked a global trend when she wore boyfriend jeans. The loose-fitting pants and masculine aesthetic contrasted beautifully with her ultra-feminine figure.

What Is a Boyfriend Shirt? 

Technically, a boyfriend shirt is a unisex loose-fitting shirt. Boyfriend shirts can be either a boyfriend T-shirt or a button-up shirt with long sleeves, collars, and a front pocket. A boyfriend shirt is an effortless way to have a stylish, feminine look over jeans or other pants. 

While you can raid your boyfriend’s closet for an oversized shirt, you can also buy a boyfriend shirt that’s designed for women. 

2310035 Sydney Oxford Boyfriend Shirt HTB 1 1440x
Source: Outerknown

The History of Boyfriend-Style Dressing

We have already mentioned the incomparable Marilyn Monroe, but the history of women wearing menswear goes back even further than the 1960s. In the 1800s, women were expected to wear uncomfortable tight-fitting whalebone corsets, long skirts, and cumbersome dresses. A women’s rights activist named Amelia Bloomer saw this style of dressing as unnecessary (and rightly so!). 

Bloomer introduced (you guessed it!) bloomers. Bloomers were long, loose pants that went all the way down to the ankles. These pants allowed women more freedom, and most importantly, they weren’t as harmful to women’s health as the fashion of the time. 

Several decades later, in the 1930s, movie stars such as Marlene Dietrich and Katharine Hepburn had both men and traditional women raising their eyebrows in disapproval when they started wearing menswear-style fashion. 

Source: Shein

During World War II, women began taking more jobs that involved physical labor, and the move toward women wearing masculine clothing quickly gained momentum. After the war, most women returned to dressing in feminine clothing, but by the time the 1960s and 1970s rolled around, the menswear-inspired fashion trend took off, and it shows no sign of going anywhere anytime soon. 

The Difference Between Boyfriend Shirts and Men’s Shirts

Women’s boyfriend shirts were modified from men’s dress shirts for a relaxed fit than traditional tailored women’s clothing. A boyfriend shirt that’s designed for women has a more feminine fit than a man’s shirt, but the long sleeves fit better than a men’s shirt does. Boyfriend shirts curve in for a more natural waist, and they usually have a capped sleeve. 

How to Style a Boyfriend Shirt

The most popular way to wear a boyfriend shirt is to throw it on with a pair of ripped tighter-fitting jeans. However, you can dress boyfriend shirts up for a chic, effortless vibe. Here are some creative ideas for styling a boyfriend shirt. 

Fun Casual

A boyfriend tee doesn’t have to be solid-colored. Now, women can enjoy styles that have traditionally been reserved for men. For example, Consider boyfriend tees such as Batman T-shirts or a vintage Coca-Cola tee for a fun, casual look. 

2310042 Sydney Boyfriend Shirt MGB 1 1440x
Source: Outerknown


If you work in a casual office environment, a boyfriend shirt looks great with pants and a pair of boots or flats. You can dress this look up with dainty jewelry that offsets the casual style of a boyfriend shirt. Another option is to style a white boyfriend shirt with dark denim and a colorful blazer. 

Casual Date Night

When date night comes around, the last thing you want to do after a busy workday is spend hours getting dressed up. Instead, pull on your favorite pair of leggings or vegan leather pants and pair them with a white or colored boyfriend shirt. 

To make this look dressier, add an arm party with thin and chunky bangles, a small choker chain, and diamond earrings. 

Girls’ Night Out

For glam girls’ night style, nothing beats a boyfriend T-shirt or loose button-down shirt. You can wear your boyfriend shirt over any type of pants, including jeans. Another idea is to pair your boyfriend shirt with a solid-colored skirt. Feel free to wear your stilettos with this look. Heads will be turning!

2310031 Sydney Silky Boyfriend Shirt PCH 1 1440x
Source: Outerknown

Flirty Weekend Looks

For running errands, attending kids’ weekend activities, or enjoying a lazy lunch with friends, consider wearing a boyfriend T-shirt with a comfy-casual skirt. Finish this look with flats or sandals and a chunky necklace. 

Girlfriend Shirt vs. Boyfriend Shirt

In our research for this article, we learned that some clothing brands offer both a “girlfriend shirt” and a “boyfriend shirt.” These styles look nearly identical, with just a couple of key differences. 

  • Roominess: The boyfriend shirt is oversized and roomier by design. Alternatively, the girlfriend shirt fits truer to size. 
  • The sleeves of the boyfriend shirt are boxier, roomier, and come down to just below the elbows. On the girlfriend shirt, the sleeves stop above the elbow.
  • The boyfriend shirt is slightly longer than the girlfriend shirt, which gives it a more elegant look. On the boyfriend shirt, the bottom of the shirt reaches to slightly below the hips, while the girlfriend shirt stops right above the hips. 

Dive into Boyfriend Shirt Style

The menswear style trend is probably here to stay, and what’s not to love? The boyfriend shirt is a stylish way to dress up or dress down, and it works well for people of all ages. Are you ready to dive into boyfriend style? Go for it!