8 Ways To Wear Oversized T-Shirts

8 Ways To Wear Oversized T-Shirts



When looking for an everyday outfit, wearing oversized t-shirts can easy option for styling. This article explores the nuanced differences between a t-shirt that is merely 'too big' and one that is oversized. While both may seem similar, achieving the right oversized look requires careful consideration of fit and proportion to enhance rather than diminish style. This article will explore how you can select an oversized t-shirt that flatters your frame and elevates your wardrobe, ensuring that your casual wear never looks like an afterthought.

How An Oversized T-Shirt Should Fit

Despite what some people believe, there's a big difference between a t-shirt that is simply 'too big' and an oversized tee. An oversized top should always be fitted to suit your frame, otherwise it looks less chic - like you've dragged it out of your laundry hamper!

So, how should an oversized tee fit? Well, here are a few key factors to consider when you want to add one of these stylish pieces to your wardrobe (and yes, this goes for both men's and women's oversized t-shirts!):

  • Loose fit: An oversized tee should have a loose fit throughout the body, giving you a relaxed and effortless look. It should never cling to your body but instead drape effortlessly, giving you more freedom of movement so that you feel incredible and comfortable.

  • Length: Although the length of an oversized t-shirt can vary, it typically falls just below your waist or your hip. The longer length is what adds to the relaxed vibe and offers more coverage, especially when it's worn over more slim-fitting pants or shorter pants like cycling shorts.

  • Shoulder seams: The shoulder seam of your shirt should always align with your shoulders - without pulling, hanging, or stretching. The top should also sit on your shoulders without feeling tight. After all, we're going for a loose, comfortable piece of clothing.

  • Sleeves: Unless you're picking a sleeveless tee, it's important to pick one with sleeves that are proportionate to the overall size of the shirt itself. They can be long or short - or somewhere in between - but they should always suit the overall style of the tee.

  • Neckline: Since we're going for a relaxed and understated look, the neck of your tee is really important. The neckline should never hang or look stretched out. No matter whether it's a crew, scoop, or even V-neck, it should fit your neck correctly without being too loose or too tight.


The Best Oversized T-Shirts

If you want to elevate your wardrobe with premium oversized tees, then Represent has some amazing options. These tees have been meticulously designed for style, comfort, and individuality. From bold graphics to understated luxury, our range of tees embodies modern fashion with a casually chic aesthetic.

Represent Owners Club T-Shirt

The Represent Owners Club T-Shirt is a testament to luxury and exclusivity. Made from medium-weight cotton, this jersey tee has a slightly oversized fit, giving you space and comfort rolled into one. It also boasts a ribbed crewneck collar with bold graphic branding on the back, meaning you'll always make a statement with this shirt.

Overall, this oversized t-shirt has a wide and square silhouette, which is perfect if you want both style and comfort. Plus, it comes in almost every colour, making it easy to add to your existing wardrobe.

Initial T-Shirt

Another one of our top picks is the Initial T-Shirt: the epitome of understated luxury and sophistication. Made from mineral-dyed 205 gsm jersey cotton, it has a sense of refinement that is really hard to find in an oversized top! Luckily, the Initial Tee does it effortlessly.

With its boxy look and premium jersey construction, this t-shirt is an ideal choice for anyone who wants a timeless staple piece that will go with anything. The external overlock seams and cropped arm length also add a unique edge, while the embroidered Initial logo at the back gives it an extra touch of style.

Spirits of Summer T-Shirt

Want more of a laid-back style? Then the Spirits of Summer T-Shirt has you covered. Like all our tees, this piece is made from the finest fabrics. But what really makes it stand out is the captivating pigment dye and spray that we've used, giving it a mesmerising gradient wash that makes each and every tee one-of-a-kind.

Additionally, this tee comes with the Spirits of Summer puff print graphic on the back and front, adding more dimension to the design. Finished with a Represent metal logo bar at the hem, the Spirits of Summer tee is a standout when you want to combine sophistication with effortless cool.


Ways To Style Oversized T-Shirts

Layering oversized tees with a varsity jacket

Layering a varsity jacket over an oversized t-shirt exudes an understated chic with contrast between the sporty feel of the jacket and the relaxed feel of the tee. What we really love is that this style is super adaptable, making it ideal for everything from casual hangouts with friends or relaxed weekend get-togethers.

To get the look, you can pair a tee like the Heavyweight Initial T-Shirt with the Cherub Wool Varsity Jacket. The crisp white tee beneath the jacket will create a good amount of contrast while tying in the colour design of the jacket's graphics. Simple and understated, yet stylish and on-trend!

Styling oversized tees with sweatpants

For some urban flair, you can always pair an oversized t-shirt with a pair of well-fitted sweatpants. No matter where you're going - running errands, chilling with friends, or just lounging at home - this combo is unbeatable when it comes to comfort.

For a laid-back yet put-together look, consider pairing a bold graphic tee like the Enduring Spirit T-Shirt with a pair of tailored sweatpants, like the Represent Owners Club Sweatpant. This monochromatic look will create a silhouette that is sleek and clean, which complements the slouchy aesthetic of this ensemble perfectly.

Wearing an oversized t-shirt with denim

Denim is timeless - and for a good reason. You can dress it up or down for a unique look every time, and the options are endless when it comes to pairing denim with an oversized tee!

One of our favourite looks is adding a neutral-coloured top to a pair of loose-fitted jeans, like our R3CA Cargo Denim Jeans. This breezy look is great for an everyday casual outfit.

If you want something a little more form-fitting that can transition from every day to a casual night out, our R2 Straight Leg Denim Jeans are a great pick. For both of these looks, a more understated tee like this Mascot T-Shirt works perfectly.

Of course, you don't have to limit yourself to denim bottoms. A denim jacket can also elevate your oversized top, especially when you pick a contemporary piece like our R4 Monogram Denim Jacket. You can wear it open for a casual look or let the bottom of your tee have a peek-a-boo moment for a more sleek aesthetic.

Smart casual oversized t-shirt outfit

You wouldn't usually associate the words 'formal' or 'smart' with an oversized t-shirt. But in reality, it's really easy to take a casual, loose-fitted tee from casual to smart - it just takes a little accessorising and careful consideration of what you pair your tee with.

For example, you can create the perfect smart-casual outfit by pairing a plain oversized tee like the Heavy Initial T-Shirt in Stained Black with more fitted trousers like the Wide Tailored Pant. Then, it's just a matter of adding the finishing touches to your outfit.

To elevate your look, a simple Trouser Chain can take your overall ensemble from drab to fab in seconds. A chic pair of glasses keeps your outfit casual while maintaining its overall smart and well-put-together look. We highly recommend a pair of our Represent California Sunglasses!

Summer oversized t-shirt outfits

Baggy, oversized tees don't only go with longer trousers. They're the perfect item for your summer wardrobe! For a breezy summer outfit that will keep you cool and comfortable, you can't go wrong with a slouchy tee, shorts, and some fashion-forward accessories.

To show you just how stylish these outfits can be, we've put together a full ensemble:

Incorporate shirting layers with oversized tees

An effortless way to elevate your shirt game is to add simple layers. Yip - it's really that simple! Again, here you have a few options that could help you to create an outfit that changes the game.

You can layer a graphic tee like our Higher Truth T-Shirt with a plain overshirt like the Black Bowling Shirt. If you want to express yourself more outwardly, a plain tee like the Flat White Heavyweight Initial T-Shirt with a graphic overshirt like the Higher Truth Shirt will ensure you're always dressed to impress!

Go with a baggy fit

Step out in style - baggy style - with a fashionable oversized T-shirt with a baggier outfit all around. Since oversized tees already have a relaxed and roomy silhouette, they pair perfectly with baggier pant styles for a laid-back look.

A good pair of baggy jeans like R3 Initial Baggy Denim Jeans (or really any of our baggy jeans) can give you a more casual look. And, while baggy cargo pants still give off a relaxed look, they can give your outfit a little more pizazz if you don't want the old denim-and-a-tee look. We'd highly recommend the R3CA Cargo Denim Bottoms to tie this ensemble together.

Best footwear to pair with oversized t-shirts

When it comes to styling oversized shirts, consider your footwear carefully to maintain balance and proportion in your outfit. Oversized or chunkier footwear styles are perfect and maintain a sense of cohesion throughout the entire look.

Some of the best chunky sneakers include our Studio Sneaker or Bully Sneaker, both of which come in several colour variations that can transform your outfit and create a more uniform aesthetic.


To conclude, the perfect oversized t-shirt should strike a balance between comfort and style, creating a relaxed yet sophisticated aesthetic. Adhering to key fit parameters, such as loose fitting yet proportional sleeves, appropriate lengths, and well placed seams are absolutely key to nailing this garment. Whether paired with some slimmer fitting jeans or layered under a sophisticated jacket, an oversized t-shirt can be a versatile and fashionable choice for an array of occasions. Remember, the ultimate goal is to create a look that feels effortless and looks impeccably chic, proving that sometimes, bigger really is better.