15 Unique & Trendy Ways To Style An Oversized Shirt In 2025

In 2025, an oversized shirt is a wardrobe must-have. When styled correctly, an oversized shirt can add an air of effortlessness to any outfit. But, styling larger garments can be tricky! An oversized shirt without the correct pieces to pair it with can swallow you up and make you look sloppy. As ample blogs, celebrities, and influencers have shown us, styling an oversized shirt doesn’t have to be a herculean task. At the end of the day, fashion is supposed to be fun! But, don’t you worry, we’ve got you! We will break down a few simple ways in which you can style an oversized shirt without compromising on your style.

The secret to styling an oversized button-down shirt lies in the layering. Pairing the large silhouette with a slim-fit skirt, a chunky belt or high-waist jeans will help to subtly emphasize your waistline. You can also opt for a sporty look by wearing it open with a tank top. Or, you can pair it with sleek trousers for a more polished and refined look. The moral of the story is- an oversized shirt can be the most versatile piece of clothing in your wardrobe when the styling is on point! And the purpose of this blog is just that. Without further ado, let’s deep dive into the most fun, chic, and trendy ways you can style your oversized shirt in 2025.

15 Stylish Ways To Style An Oversized Shirt

It isn’t every day that we come across a trend that looks good and is extremely comfortable. Enter, oversized shirts. We’ve rounded up 15 trendy ways of styling this wardrobe staple that’ll make you look like the coolest cat on the street!

1. With high-waisted jeans

In this look, you can tuck in your oversized shirt in a pair of high-waisted jeans. In this way, you won’t feel gobbled up by the oversized silhouette. You can also add a belt to add extra emphasis on your waist. Complete the look with heels or ballet flats to add an air of effortlessness.

2. With denim shorts

For warmer days, simply wear your oversized shirt over a pair of denim shorts. You can choose to tuck in or not. Top off the look with cool sunglasses and a pair of sneakers. This daytime look guarantees comfort and an overall too-cool-to-care vibe.  

3. With sleek trousers

If ‘back to work’ is your vibe, an oversized shirt with a sleek pair of trousers is the ultimate combination for you! Complete the look with minimal accessories, strappy heels, or pumps for the perfect dressed-up look.

4. With a sweater

The oversized shirt, sweater, and skirt combination sounds preppy but is a perfect example of understanding how to balance an outfit without much effort. You can switch the sweater with a sleeveless vest too. Complete the look with a pair of tights, knee-high boots, and minimal jewelry.

5. With tank top and wide-leg trousers/jeans

This look is all about creating the right balance. The oversized silhouette of the wide-leg trousers/jeans and the shirt can be slimmed down by wearing a tank top. We suggest, wearing the oversized shirt open on top of the tank top. You cam complete the look with a pair of ballet flats or sneakers.

6. As a dress

Haven’t got anything to pair an oversized shirt with? No problem, just wear it as a dress! Aim for a casual and effortless look by styling the oversized silhouette with a pair of knee high boots and you are good to go for the day!

7. With a lean maxi skirt

Another interesting way to create a balanced outfit with an oversized shirt is to pair it with a lean maxi skirt. If you are bored with wide-leg jeans or slim-fit trousers, a maxi skirt is the best way to ruffle things up. You can elevate this look by adding minimal jewellery and a pair of stilettos.

8. With cycling shorts

Here's an easy but chic way to style an oversized button-up: wear it with fitted bottoms such as cycling shorts, leggings, or even a mini skirt for a well-proportioned silhouette. This pairing gives off super-relaxed cool-girl vibes; to keep it casual yet purposeful, don some sneakers or chunky sandals.

9. Cinched with a belt

By cinching it using the belt around the waist, transform your oversized shirt into a chic shirt dress. This is a simple tip that can outline that hourglass frame for you, relaxed and stylishly. Roll the sleeves up and pop on some sneakers for an everyday look or switch to heels for an elevated touch.

10. Layered with a vest

Layer an oversized shirt with a vest for an easy, trendy update. Be it a structured waistcoat or a cozy knitted vest, this layering technique adds extra dimension and plays with necklines and proportions. Very preppy or vintage style in your outfit!

11. Monochrome magic

Immediately, the oversized look gets that touch of class by literally dressing from head to toe in one shade. Put your oversized shirt over matching-color trousers, skirts, or shorts for tightening up that put-together, sleek aesthetic and matching heels for that monochromatic finish or match it with some Western boots for that sultry contrast.

12. Matching bottoms & bra

Leave the oversized shirt open unbuttoned and pair it with matching bottoms and a peekaboo bra for that effortless sultry look. Whether you're in sneakers, loafers, or strappy heels, you definitely will get that "chic pajama set" feel with an on-trend twist.

13. With a corset top

Layer in a corset top over the oversized shirt to elevate the style of the oversized shirt dress trend. This waist-cinching trick gives structure, introduces a new-age edgy touch, and achieves the desired effect—especially works like a sheer long-line corset, as it allows any prints or graphics on your tee to permeate subtly.

14. Leather jacket and boots combo

Wish to combine your oversized T with a cool, rock-chic effect? Then a motorbike structured leather jacket over it plus some chunky platform boots should do the trick. Finish that look off with bold jewelry, and you will have a dedicated grunge rock inspired style statement.

15. As a shacket

In fact, an enormous tunic shirt can work as a lightweight jacket-a.k.a. "shacket" for transitional weather. This is the layering piece, which adds warmth and an extra touch of fashion style. Leave it open over the fitted clothes and cinch it for a more structured look. Add a crossbody bag and sunglasses to this street-style-approved finish.

Where to shop for oversized shirts?

One can opt for oversized shirts from different brands such as Zara, HnM, and COS, or search on online shopping websites such as GoFynd and ASOS. You could always try your luck at thrift stores and vintage shops. Let's check out some sites with fantastic prices for oversized shirts, shall we?

1. GoFynd

Shopping here brings in great and excellent options of oversized shirts that are designed stylishly yet comfortable. With their main focus on streetwear, athleisure, and casual fashion, the site is a hotbed of oversized silhouettes from the best-selling brands so that you just might find the perfect relaxed-fit look.

2. Myntra

Being one of the largest fashion platforms in India, Myntra has a fabulous collection of oversized shirts for every style- be it minimal basics, bold prints, or designer-inspired looks. Whatever defines your look, you will get it here- be it high street or premium.

3. Ajio

Standing out with funky and avant-garde styles, Ajio is a great hub for oversized shirts where you can garb up clothes that have unique cuts, patterns, and other styling details. Dazzling up the collections with plenty of domestic brands is improper but definitely very encouraging.

4. Urbanic

If you're a fan of influencer-inspired fashion, Urbanic is the place to go when it comes to oversized shirts oozing modernized chic appeal. This is the place for trendy, stylish statement pieces that combine comfort with fashion. These can either wear out on their own for casual days, or can be worn mixing up with some accessories for an elevated look.

5. ASOS

ASOS is a very reputed global fashion hub having one of the broadest portfolios of oversized shirts on the planet. Whether you like classic minimalist fits or striking street-style ones, you have them all here under different brands and designs to cater to every aesthetic type. Oh, and their inclusive sizing also ensures a perfect fit for all.

6. Amazon Fashion

For oversized shirts with amazing variety but low prices, Amazon Fashion is the right choice. Local or imported brands from classic button-downs to big oversized graphic tees have something for every occasion and every price point.