15+ Ways To Style An Oversized Shirt

Oversized shirts have become a beloved staple in many wardrobes for their comfort, versatility, and effortlessly chic appearance. Whether you are aiming for a casual, laid-back vibe or trying to make a bold statement, an oversized shirt can be your go-to piece. With the right styling, it can be worn in countless ways to suit any occasion. In this article, we’ll explore 15 trendy ways to style an oversized shirt, making it a key player in your wardrobe rotation.

From pairing it with different types of bottoms to layering it with accessories, an oversized shirt offers a multitude of styling options. It’s ideal for days when you want to be comfortable yet stylish, and with the following ideas, you’ll be able to transform your oversized shirt into an outfit that turns heads.

With summer in full swing, it’s time to get extra creative when putting together the perfect baggy outfit. From mixing patterns, to dressing up sweatshirts with heels, to pairing western boots with menswear-inspired button-downs, we’ve rounded up 10 of our favorite takes on this must-have style, ahead.

Fun Fact

Oversized shirts became a popular fashion statement in the 1990s and were often associated with hip-hop culture, symbolizing comfort, confidence, and a laid-back attitude.

15+ Trendy Ways To Style An Oversized Shirt

1. Tucked in with High-Waisted Jeans

One of the easiest ways to style an oversized shirt is to tuck it into a pair of high-waisted jeans. This look gives you a defined waist while maintaining the relaxed fit of the shirt on top. Opt for mom jeans or straight-leg jeans to create a laid-back yet polished outfit. Pair it with sneakers or ankle boots to complete the look.

2. Belted as a Shirt Dress

Turn your oversized shirt into a stylish shirt dress by adding a belt at the waist. This styling helps create an hourglass silhouette and makes the outfit more feminine. Wear it with knee-high boots or sandals, depending on the weather, and accessorize with statement jewelry to elevate the look.

3. Layered Over a Crop Top and Leggings

For a sporty and comfortable look, wear your oversized shirt open over a crop top and a pair of leggings. This outfit is perfect for running errands or hanging out with friends. You can tie the shirt at the waist for added style, and wear it with sneakers for an easy, relaxed vibe.

4. Knotting the Front

Knotting the front of an oversized shirt is a great way to add some shape and structure to your outfit. You can pair it with high-waisted shorts or skirts to create a playful and casual look. This style is especially great for summer outings and can be worn with sandals or casual flats.

5. Off-Shoulder Look

Create an off-shoulder look by letting one side of your oversized shirt fall off your shoulder. This styling adds a touch of femininity and can be paired with denim shorts, skinny jeans, or a mini skirt. Accessorize with layered necklaces to add a chic flair to the outfit.

Trivia

The oversized shirt trend gained significant momentum in high fashion when celebrities like Julia Roberts wore her husband’s oversized white shirt on the red carpet at the 1990 Golden Globe Awards, making it a fashionable and bold statement.

6. Layered Under a Sweater

Oversized shirts are perfect for layering under sweaters, especially during the cooler months. Let the collar and hem of the shirt peek out for a preppy look. You can pair this with jeans or tailored pants and complete the outfit with loafers or ankle boots for a sophisticated look.

7. Half-Tucked with Leather Pants

For an edgy look, try half-tucking your oversized shirt into a pair of leather pants. This asymmetrical style adds visual interest and keeps the outfit casual yet cool. Pair it with ankle boots or heeled sandals to add some height and create a bold statement.

8. Paired with Biker Shorts

An oversized shirt paired with biker shorts is a trendy and comfortable combination. This athleisure-inspired look is perfect for casual outings and can be paired with chunky sneakers or slides. Accessorize with a baseball cap or a mini backpack to complete the sporty look.

9. Layered Over a Slip Dress

Layering an oversized shirt over a slip dress adds a casual element to an otherwise feminine outfit. You can leave the shirt unbuttoned for a relaxed look or tie it at the waist to add some definition. Wear this outfit with strappy sandals or flats for a chic and effortless vibe.

10. French Tuck with Tailored Trousers

The French tuck—where you tuck in just the front of your shirt and leave the back loose—is perfect for styling an oversized shirt with tailored trousers. This look is great for a business-casual setting and gives you a polished yet comfortable feel. Pair it with loafers or heels for an office-ready outfit.

Did You Know

Did you know that oversized shirts are considered a gender-neutral style staple? They can be worn by anyone, regardless of gender, and their versatility makes them a popular choice for both casual and formal occasions.

11. Tied Around the Waist

Another casual way to style an oversized shirt is to tie it around your waist. This is a great way to add some style to a basic t-shirt and jeans combo. It also comes in handy as an extra layer when the weather gets chilly. Pair it with sneakers to keep the outfit comfortable and relaxed.

12. Under a Blazer

Layering an oversized shirt under a fitted blazer can create a stylish juxtaposition between the loose and structured elements. Pair it with jeans or tailored pants and add heels for a sophisticated and fashion-forward look that works for both casual Fridays and weekend outings.

13. Paired with a Mini Skirt

For a cute and playful look, pair your oversized shirt with a mini skirt. You can tuck the shirt in or leave it loose, depending on the style you’re going for. This outfit is perfect for a day out, and you can complete it with ankle boots or strappy heels.

14. Worn as a Beach Cover-Up

An oversized shirt can also double as a stylish beach cover-up. Throw it over your swimsuit when you’re heading to the beach or the pool. Leave it unbuttoned for a breezy look, and pair it with flip-flops and a straw hat for the perfect beach-day ensemble.

15. Layered with a Corset Belt

To add some edge and structure to your oversized shirt, wear a corset belt over it. This helps define your waist and creates a statement look. Pair this outfit with skinny jeans or leggings and heeled boots for a bold and confident style.

16. Pattern Play 

Having great style means confidently breaking the rules. You can wear an oversized striped shirt with colorful pants. In this case, it’s all about the colors — the cool tones of pink and red make this pattern combination work.

17. The Classic Combo

Speaking of different combinations, a classic, crisp white button-down and jeans never fails. With some of your shirt buttons undone, including your cuffs, you’re telling the world you’re serious but can chill out, too. Whether you complete the look with boots, sneakers, or heels, all are acceptable options that work for brunch, date night, or the office.  

18. Just Add Sneakers

Pull a Hailey Baldwin or Emily Ratajkowski and style your oversized shirt with white sneakers, such as Nike Air Max or a trusty Cortez pair. Tiny cutoffs or bike shorts will create that celeb-approved no-pants look, otherwise you can slip on a longer, Bermuda option and let them peek out.

Oversized shirts are versatile pieces that can be styled in numerous ways to create trendy and fashionable outfits for any occasion. Whether you’re aiming for a casual, laid-back look or something more polished and structured, an oversized shirt can easily adapt to your needs. With these 15 trendy styling ideas, you can confidently experiment with different outfits and find the ones that suit your style and personality best. So, grab your favorite oversized shirt and start creating some stunning looks today!