The best ways to style oversized t-shirts for a chic look

November 27, 2023

In the world of fashion, the oversized trend never seems to lose its appeal. The oversized t-shirt, in particular, is a staple item in many wardrobes, recognized for both its comfort and versatility. Yet, achieving an effortlessly stylish look with an oversized shirt, instead of appearing swamped in fabric, can sometimes feel like a daunting task. But fear not, because we are here to guide you. In this article, we will explore the numerous ways to style oversized shirts, pairing them with jeans, shorts, skirts and more to create fashionable outfits that cater to your personal style.

Pairing with Jeans

There is a certain classic appeal to pairing an oversized shirt with jeans. This combination is a casual, yet stylish option that is versatile enough for various occasions. The trick to mastering this look is to balance your proportions.

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You want to prevent the outfit from becoming too baggy or shapeless. Therefore, pairing your oversized tee with skinny or straight-leg jeans will add some structure and form to your silhouette. If your shirt is especially long, consider doing a half or full tuck to add a level of sophistication and prevent the outfit from looking too sloppy. To finish off the look, accessories like a statement belt or a chic handbag can add some personality to the ensemble.

Dressing Up with a Skirt

One of the great things about oversized shirts is that they can easily transition from a casual day look to a more dressy evening outfit. And this is particularly true when you pair your shirt with a skirt.

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Whether it’s a mini, midi, or maxi skirt, the combination of an oversized shirt adds a certain level of chicness that is hard to match. For a more relaxed look, try a loose knot at the waist of your shirt over a midi skirt. If you’re in the mood for something more classy, tuck your shirt into a high-waisted pencil skirt. It’s a very stylish look that screams sophistication.

Going Casual with Shorts

When the warmer weather kicks in, pairing your oversized shirt with shorts can create a comfortable, yet fashionable casual look.

Just as with jeans, it’s important to balance your proportions when wearing shorts. Opt for shorts that are more fitted and not too long – think denim cut-offs or tailored shorts. If your shirt is particularly oversized, try tucking it in or tying a knot at your waist to prevent your figure from being completely swallowed up by the fabric. Add some sandals or sneakers, and you’ve got a relaxed summer outfit that is both stylish and comfortable.

The Oversized T-Shirt Dress

Another popular way to style an oversized t-shirt is to wear it as a dress. This look is a trendy, comfortable option that’s perfect for those days when you want to keep it simple, yet stylish.

The key to this look is ensuring the shirt is long enough to be worn as a dress. Pair it with some chunky sneakers for a casual daytime look, or dress it up with some strappy heels for an evening out. Adding accessories like a statement belt or a crossbody bag can add some extra flair and make the outfit more unique.

Layering with an Oversized Shirt

Layering provides an opportunity to add some depth and dimension to your outfit, and an oversized shirt is the perfect piece for this.

You can wear a cropped jacket or a blazer over your shirt for a sophisticated look, or add a long coat for a dramatic effect. Layering a thin tee underneath an oversized shirt can also be interesting, especially if the shirt has a unique design or cut-out. Layering not only makes your outfit more intricate and stylish, but it also allows you to adapt to changing weather conditions.

Making a Statement with Accessories

Accessories will always play a huge role in completing any outfit. This is especially true when styling oversized shirts, as they can help break up the bulkiness and add some visual interest.

Use belts to cinch in your waist and create a more defined silhouette. Statement necklaces or earrings can draw the eye and add some sparkle to your outfit. A stylish handbag or a pair of cool sunglasses can also elevate your look. Remember, the key is to choose accessories that complement your outfit rather than overwhelm it.

The world of oversized t-shirts is one full of style and comfort. With just a bit of imagination and creativity, you can transform this basic garment into a chic and trendy outfit. So, go ahead and experiment with different styles and looks. You may be surprised at just how versatile your oversized shirt can be.

Oversized Shirt with a Denim Jacket

Adding a denim jacket to your oversized shirt outfit can transform your look entirely, making it especially trendy and cool. Denim jackets are a timeless staple that never go out of fashion, which makes them an excellent piece for pairing with your oversized shirt.

For a complete look that is both comfortable and stylish, try a light-washed denim jacket over a white or brightly coloured oversized shirt. For a more vintage vibe, a dark denim jacket over a printed or graphic tee can make a bold statement. To ensure balance and avoid looking drowned in fabric, it’s essential to choose a denim jacket that is fitted and not too long.

Make sure to roll up the sleeves of your jacket for a relaxed, easy-going look. This can also help to show off the sleeves of your shirt. If you want to make your outfit more feminine and flattering, you can tie a knot in the front of your oversized shirt, just above your waistline.

For the bottom, consider wearing skinny jeans or fitted trousers. This will help create an appealing contrast with the oversized top. Complete your outfit with a cool pair of sneakers or ankle boots and don’t forget to accessorize with a trendy backpack or crossbody bag.

Styling Oversized Shirts for All Seasons

Believe it or not, your oversized tee has the potential to be a year-round staple. It’s all about knowing how to style it appropriately for each season.

During the warmer months, opt for a casual look by tying your oversized shirt at the waist and pairing it with high waisted shorts or a cute mini skirt. A pair of sandals and a straw hat could be your go-to accessories for a summer-ready outfit.

As temperatures start to drop, your oversized shirt can be paired with skinny jeans or leggings. Add a chunky knit cardigan for extra warmth and style. Ankle boots and a big scarf can add a cozy feel to your outfit.

In colder weather, layering is key. Wear your oversized shirt under a warm coat or a stylish blazer. You can also add a thermal turtleneck underneath for extra warmth. High-waisted jeans or thick leggings and knee-high boots can complete the look.

Remember, the beauty of an oversized shirt lies in its versatility. It can be dressed up or down, layered or tied, tucked in or left out. It’s truly a fashion staple that everyone should have in their closet.


In conclusion, styling oversized shirts is about striking a balance. It’s about mastering the art of proportions and knowing how to use accessories to your advantage. So, whether you’re pairing your shirt with jeans, a skirt, shorts or wearing it as a shirt dress, remember the importance of balance.

Experiment with different styles and find what works best for you. With the right combination, your oversized shirt can be your go-to piece for a chic and comfortable look.

Remember, an oversized tee isn’t just a piece of clothing; it’s a fashion statement. So, put on your statement piece and wear it with confidence. After all, confidence is the best accessory you can wear.