How to Style Oversized Shirts: 14 Fashionable Looks - Maves Apparel

How to Style Oversized Shirts: 14 Fashionable Looks

Oversized shirts have become a major trend in the fashion world, and for good reason. Not only do they offer a comfortable fit, but they also exude a stylish and effortless vibe. However, there is a fine line between looking intentionally fashionable and appearing sloppy when it comes to styling oversized shirts. To help you master this trend, we have curated 14 fashionable looks that will make you look like a street style star. From monochromatic matching sets to casual but modern pairings, these outfit ideas will take your oversized shirt game to the next level.

1. Start Simple with a Monochromatic Matching Set

One of the easiest ways to style an oversized shirt is by opting for a monochromatic matching set. This coordinated look instantly elevates the loose-fitting silhouette of the shirt. You can choose a set in a neutral color like black or white, or go for a bold hue to make a statement. Pair your oversized shirt with matching trousers or a skirt for a cohesive and polished look. To add a touch of unexpected flair, consider pairing the ensemble with western boots or other unconventional footwear.

2. Knot Your Average Shirt for a Chic Twist

For a trendy and stylish twist on the oversized shirt, try knotting it at the front to create a crop top effect. This simple styling trick instantly adds shape and definition to your outfit. Pair the knotted shirt with high-waisted trousers or a long skirt to accentuate your curves. The combination of the loose-fitting shirt and the fitted bottoms creates a flattering silhouette that is reminiscent of a bodycon dress. This look is perfect for both casual and dressier occasions.

3. Add a Preppy Touch with a Structured Vest

To give your oversized button-down shirt a preppy and sophisticated touch, layer it with a structured or knit vest. This combination adds a touch of academic-inspired style to your outfit. You can choose to add a tie for a more traditional prep school look. Pair the shirt and vest combo with your preferred bottoms, whether it's tailored trousers or a skirt. This outfit is perfect for achieving a light academia aesthetic while maintaining a polished and put-together appearance.

4. Go Classic but Modern with Shorts

Pairing an oversized top with shorts is a timeless and versatile combination that works well in any weather. For a classic and coordinated look, opt for a black-and-white color palette. However, to keep the outfit from feeling stale, pay attention to the details. Consider incorporating a zebra print skirt or mismatched footwear to add a playful spin to the ensemble. This combination of casual and modern elements creates a fashionable and eye-catching look.

5. Tuck and Accessorize for a Chic Transition

On warm fall days, you can elevate your oversized graphic tee by tucking it into a pair of baggy shorts. This combination creates an effortless and laid-back look that is perfect for transitioning from day to night. To enhance the overall style, add a chunky statement necklace and a structured jacket. These accessories will help pull the outfit together and make it suitable for various occasions. Whether you're running errands during the day or going out for drinks in the evening, this outfit will keep you looking chic and stylish.

6. Go Minimalist with an Oversized Muscle Tee

For a minimalist and effortlessly cool look, try styling an oversized muscle tee. Pair it with baggy trousers or leather joggers for a relaxed and understated vibe. This combination is perfect for casual outings or after-work drinks. The loose-fitting muscle tee adds a touch of edginess to the outfit, while the baggy bottoms maintain a comfortable and relaxed feel. This look is ideal for those who prefer a more laid-back and minimalist approach to fashion.

7. Stick with the Timeless Combo: Oversized Button-Down and Jeans

When in doubt, you can never go wrong with the timeless pairing of an oversized button-down shirt and jeans. This classic combination exudes a sense of effortlessness and versatility. To add a touch of personality to the outfit, leave a few buttons undone, including the cuffs. This casual styling choice sends the message that you are serious yet laid-back. Whether you're running errands or meeting friends for lunch, this outfit will always be a reliable go-to option.

8. Coordinate Your Look with a Matching Shirt and Bottoms

For a coordinated and sexy look, try wearing an unbuttoned oversized shirt with matching bottoms and an exposed bra. This monochromatic ensemble is both stylish and attention-grabbing. The best part is that you can pair it with any shoes you desire, whether it's sneakers or slip-on loafers. This outfit is perfect for those who want to make a bold statement and showcase their fashion-forward style. It can be worn for a night out or a special occasion where you want to stand out from the crowd.

9. Embrace the Baggy Look from Top to Bottom

Sometimes, we all crave the comfort of going completely baggy from top to bottom. This styling choice is incredibly comfortable and gives the feeling of being effortlessly chic. Pair your oversized shirt with baggy pants or joggers and slip-on sneakers for the ultimate laid-back weekend outfit. This look is perfect for running errands, grabbing brunch with friends, or simply lounging around in style. Embrace the comfort and fashion-forwardness of the baggy trend with this easy-to-wear outfit.

10. Top Things Off with an Oversized Shirt Jacket

For those crisp in-between days, an oversized shirt can double as a jacket or "shacket". This versatile piece provides both warmth and style. Layer it over your outfit and choose whether to leave it open or button it up. You can further enhance the overall look by adding a few key accessories that will pull the whole ensemble together. This outfit is perfect for transitional weather and adds an extra dose of style to your overall appearance.

11. Explore the Lampshading Trend with Over-the-Knee Boots

For an easy and sleek outfit, try embracing the lampshading trend by styling your oversized shirt or sweater with over-the-knee boots. This combination creates a sexy and fashionable look that works year-round. It's especially perfect for those months when you want to keep your legs warm while maintaining a stylish appearance. The oversized shirt adds a relaxed feel to the ensemble, while the over-the-knee boots elevate the overall look and add a touch of sophistication.

12. Show Some Skin with an Unfastened Button-Down

If you want to add a little spice to your button-down outfit, try unfastening the top and slipping out a single shoulder. This quick styling trick instantly transforms your look and adds a touch of allure. To further enhance the outfit, incorporate elaborate jewelry, such as pearl necklaces and drop earrings. You can also play with different footwear options, depending on the occasion. This look can be dressed up or down and is suitable for a variety of events, including more formal occasions where you can trade the jeans for bare legs, tights, or trousers.

13. Cinch It In for a Modern Twist

If you want to make a statement, try wearing an oversized shirt as a dress by cinching it at the waist with a corset top. This modern update on the trend adds a unique and fashion-forward touch to your outfit. There are numerous ways to make this look your own, but a sheer long-line corset is particularly eye-catching as it allows any graphic on your tee to shine through. Experiment with different corset styles and colors to create a personalized and trendy look.

14. Layer Up for an Apple-Picking Adventure

For an early fall apple-picking adventure, you can create a chic and practical outfit by layering an oversized shirt with a turtleneck underneath. This layered look not only adds a stylish touch but also keeps you warm as the temperature begins to drop. Pair the ensemble with rugged boots to ensure you're prepared for any muddy terrain. The combination of the oversized shirt, turtleneck, and boots creates a chic and autumn-appropriate look that is perfect for outdoor activities.


In conclusion, styling oversized shirts can be a fun and fashionable way to express your personal style. Whether you prefer a casual and laid-back look or a more polished and put-together ensemble, there are numerous ways to incorporate oversized shirts into your wardrobe. From monochromatic matching sets to trendy knotted tops, there is a style for every occasion and personal preference. Remember to experiment, have fun, and embrace your individuality when styling oversized shirts.

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This article was written by Muhammad Saleem Shahzad, Managing Editor of Fashion and Manufacturing. With more than a decade of experience in the Fashion industry, Muhammad reports on breaking news and provides analysis and commentary on all things related to fashion, clothing and manufacturing.