Marilyn Monroe on set of The Misfits Credit Eve Arnold via classiq.me 

The masculine clothing on her famously feminine figure created a striking contrast. This probably helped ignite the timeless trend that has since been adopted by both celebrities and everyday individuals alike. 

Today, it’s become so popular that you can cut out the middleman (or bf): many brands offer “masculine” over-sized jeans, sweatpants, and shirts directly to women.  

Endless Styling Options 

The oversized dress shirt is a style-chameleon that can adapt to any environment. It’s just as suitable for an evening hopping between nightspots as it is for a day jumping between meetings.  

Styling this shirt for almost any situation is easy. The options are only limited by your imagination:  

• Beach Vibes: Wear it open or partially buttoned up as a breezy sun protection layer over your bathing suit or shorts. It adds a touch of casual sophistication to your beach look. 
• Work It: Tucked, untucked, buttoned or unbuttoned, it's the perfect blend of professionalism and relaxed elegance when paired with trousers, skirts, or even jeans (for those casual Fridays). 
• Casual Chic: Leave it open over a crop top, t-shirt, or tank for an easygoing classy-casual look. This can work at the office, brunch dates, or for running errands.

As you can see, an over-sized boyfriend shirt has versatility. From a comfy yet professional workplace shirt to a light beach jacket, it’s got you covered.  

Boyfriend Shirt: Bottom Combinations 

When it comes to bottoms, the boyfriend shirt can couple with just about anything. Its versatility allows you to match it with a wide range of bottoms: 

• Shorts: Whether it's denim shorts or capris, there are plenty of combos that will keep you cool and comfortable in both casual and professional situations. 
• Dress pants: Wear it with wide-leg trousers or tailored slacks and strike the perfect balance between comfort and style, ideal for the office or formal events. 
• Skirts: The contrast between the relaxed fit of the shirt and the feminine silhouette of a skirt can create a striking juxtaposition. Try experimenting with different skirt lengths, such as midi or mini. 
• Jeans: Dress it up with heels and accessories for a night out or keep it casual with sneakers for a laid-back weekend look. 

Still more versatility: Tuck and Roll! Button and Fold! 

What makes this item even more versatile is the almost infinite combinations you can achieve just by the way you wear it. There are countless fun and creative way to tuck, fold, button, and roll up this item to get a unique look. 

• Cross over tuck: Pull each side across the other, tucking each front shirttail into your pants at the opposite hip, creating an almost blazer-like V-shape for a touch of class.
• One side tucked: For a casual yet put-together appearance, tuck in just one side of the shirt and let the other side hang loose for an asymmetrical style. 
• Both sides tucked: Get a polished and tailored appearance by tucking both sides of the shirt into your bottoms. Tip: After tucking it in tightly, “scoop” or gently pull out the shirt for a relaxed look. 
• Open: Embrace an easygoing vibe by leaving the shirt open and letting it flow. This is a cool and casual summer look when layered over a crop top or tank.  
• All buttoned up: For a touch of sophistication, button up the shirt all the way to the top and pair it with a statement necklace. 
• Knotted: Add a playful twist by knotting the front of the shirt over your navel. This can accentuate your waist and add a flirty edge to your look.   
• Belted: With longer shirts, define your waist by adding a belt over the shirt. This can create a dress-like effect that goes great with leggings. 
• Off one or both shoulders: Get a bit sultry by draping the shirt off a shoulder or two. This look pairs well with a cami or crop top.

Feeling inspired? You can check online for a treasure trove of videos showcasing super creative ways to fold, twist, button, and roll your boyfriend shirt into plenty of fun and inventive styles.  

Combine these with different bottoms and accessories to create infinite looks that can suit almost any occasion. 

Make a date with a button-up boyfriend shirt 

From shorts and skirts to slacks and jeans, this shirt is your ultimate style companion. It’s a timeless piece that can elevate almost any look. The classic plain white boyfriend shirt is a staple, but you can also add pastels, stripes, and more to your repertoire.  

In conclusion, the button-up shirt is a must-have addition to your wardrobe. Remember, fashion is all about having fun, taking risks, and embracing your unique sense of personal style. So go ahead and experiment with different combinations to create your own signature look. The possibilities are endless.