How to style oversized t-shirts: The looks you need to add to your wardrobe stat

A versatile summer must-have, here's how to style oversized t-shirts according to the street style set

composite of three women in street style shots showing how to style oversized t-shirts
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Learning how to style oversized t-shirts will add infinite versatility to your wardrobe. A simple and comfortable staple, knowing how to wear it to suit your personal style is key to sartorial success.

No capsule wardrobe is complete without a collection of oversized t-shirts, but they don't just have to be reserved for lazy days at home or sweaty gym sessions. One of the easiest items to dress up or down for every season, this style essential has endless styling possibilities. From cropped boxy fits to longer tunic shapes, how oversized you go is up to you.

Pair with relaxed fabrics like jersey and denim for off-duty days, or elevate your look with pieces like luxe leather pants, silk slip skirts, and a strappy heel for more formal occasions. For a more in depth guide on how to style oversized t-shirts, you can't go wrong with these foolproof outfit formulas that will reframe how you view this slouchy wardrobe basic.

1. How to style oversized t-shirts with a blazer

How to style oversized t-shirts with a blazer

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When it comes to how to style a blazer with an oversized t-shirt, the sharp cut, structured shoulders, and longline length of a classic blazer will make even the baggiest of oversized t-shirts feel smarter. To avoid overwhelming your frame, it’s best to keep your blazer true to size, as long as there’s enough room for your t-shirt to sit comfortably beneath it without ruching the sleeves or adding unwanted volume at the shoulders. 

Robing (wearing your blazer over your shoulders like a cape instead of putting your arms through the sleeves) is a chic way to style a blazer if you find your t-shirt is too oversized for straightforward layering. When opting for a colourful or patterned blazer, choose a t-shirt in the same hue, or, keep it simple and chic with black or white version beneath to effortlessly channel the rich mom trend.

2. How to style oversized t-shirts with boots

How to style over-sized t-shirts with boots

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The category of boots is pretty broad, with a vast number of designs coming under the same fashion umbrella. Your boots could be a directional stompy pair of Doc Martens, an elegant knee-high iteration with a pointed toe and a block heel, or even a pair of cowboy boots to channel the shoe trends 2023.

The kind of boots you choose to pair with your oversized t-shirt will depend on the overall feel of your look, the length of your t-shirt and your signature style. Offset oversized t-shirts and chunky boots with a slinky slip skirt, or double-down with straight-leg dark wash jeans. If you're looking to wear your oversized t-shirt as a dress but don't want to have a lot of leg on show, try a pair of the best knee-high boots or over-the-knee boots to add extra coverage.

3. How to style over-sized t-shirts with shorts

How to style over-sized t-shirts with shorts

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Fashion’s love affair with the '80s and '90s was one of the big fashion trends 2022 and shows no signs of waning, keeping oversized t-shirts and cycling shorts very much on-trend. 

“A chic way to wear an oversized t-shirt is with tight cycling shorts, ankle socks, and trainers,” comments Farrah. “Princess Diana rocked this look and it remains on trend today. The key to this outfit is balance, and the oversized t-shirt works in perfect partnership with a tighter garment on the bottom half to balance out the silhouette.” 

That's not to say form-fitting shorts are a necessary requirement. There's plenty of potential for tailored, utility, and longline city shorts too. To keep the balance, choose a style with a nipped-in waist, or colour block with a darker shade on either your top or bottom half. 

4. How to style oversized t-shirts with jeans

How to style over-sized t-shirts with jeans

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If two pieces were to form a sartorial sisterhood, it would be oversized t-shirts and jeans. The fabrics work perfectly together for an effortless and relaxed feel. But that’s not to say this look can’t cut it for evening or smarter occasions too - you just need to consider the colour, fabrication and silhouette of both pieces and select the right type of jeans.

For daytime, go as oversized as you like with your t-shirt, rolling up the sleeves to exaggerate the effect, and team with the best wide-leg jeans or boyfriend jeans in mid to light washes (think stone blue through to white). 

When it comes to how to style oversized t-shirts for the evening, on the other hand, this requires a slightly more structured silhouette and darker tones. Ideally, your t-shirt should be more subtly oversized (think one or two sizes up from your regular size) rather than all-out baggy. Looking for silk jersey fabrics for added luxe and tuck your oversized tee into tapered straight jeans or your best skinny jeans in black or indigo and finish with a pair of on-trend heeled mules. 

5. How to style oversized t-shirts with trousers

How to style over-sized t-shirts with trousers

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We’ve fallen hard for the wide-leg trouser trend, but choosing what to wear with wide leg pants can prove tricky. The best shirts can feel too formal, and a billowing blouse too fussy, but have you tried learning how to style oversized t-shirts with a pair?

For the whole look to work in synergy, select a t-shirt in the same hue as your trousers, or, if they’re patterned, pick just one colour out from within the print, or opt for a neutral hue to tone the look down. How oversized you can go with your t-shirt is dependent on the fabric of your trousers. 

If they’re lightweight, with enough swish and movement to allow them to allude to the shape of your legs when you walk, you can get away with a long-line t-shirt, worn loose over the waistband of your trouser. Alternatively, if the fabric of your pants is starchy or structured, a cropped or shorter t-shirt is best to help you regain your shape by giving a flash of your waistband to nip you in. 

6. How to style oversized t-shirts with skirts

How to style oversized t-shirts with skirts

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Want to add a cooler edge to a pretty skirt? An oversized t-shirt grounds a skirt look, making them feel slightly more androgynous in the process. For the most flattering fit, make your skirt a high-waisted one. Anything with a low or drop waist will not only make tucking your t-shirt in tricky, but also means you lose definition around your middle. To make this look work you'll want the kind of oversized t-shirt that says you've sized up once or twice, rather than going for something overly baggy, it should feel gently relaxed. 

This look is also ideal for what to wear in the heat, as you'll get greater airflow to your skin in an oversized t-shirt. Not sure what colour t-shirt to wear with a printed or colour-pop skirt? You can’t go wrong with a classic neutral such as the best white t-shirts or a basic, plain black design. 

“In terms of colour, I always suggest that my clients have an oversized white t-shirt in their wardrobes,” says Farrah. “It will go with everything, from midi skirts to jeans, and can easily be dressed up with chunky gold jewelry and a slick of lipstick.” 

7. How to style oversized t-shirts with trainers

How to style oversized t-shirts with trainers

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Fully embrace the sporty feel of an oversized t-shirt by teaming yours with trainers - all you need to do is pick a side. The fashion industry is currently divided into two teams when it comes to trainers: sleek and streamlined, or super chunky. The former works best with long trousers, while the latter works well with anything that finishes mid-calf or above, such as the best midi dresses

Both styles of trainers are not only extremely practical, making hot-footing around town an all-around comfortable experience, but will keep your oversized t-shirt look feeling suitably relaxed. One of the easiest holiday outfit ideas for any destination, this is an outfit formula you'll turn to over and over again.