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

how to style over-sized t-shirts
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The key to how to style oversized t-shirts is all about playing with shape and proportion. So much more than a humble base layer, an oversized t-shirt has can be easily dressed up or down for numerous occasions.

Your morning Americano, cinema popcorn, handbags - most things are better when you size up and t-shirts are no exception. When it comes to how to style oversized t-shirts the sartorial possibilities are endless when you step away from form-fitting styles. How oversized you go, is down to you, and the spectrum is broad, spanning from a one-size-up-from-your-usual to long enough to pass as a tunic or a dress. 

Although t-shirts are traditionally more associated with casualwear, oversized t-shirts can also be worn in a way that feels evening appropriate too. Instead of teaming with relaxed fabrics like jersey and denim, and footwear like your trusty trainers, elevate your tee with pieces like luxe leather pants, silk slip skirts, and a strappy heel. The high-low mix will create a cool contrast, giving your look an interesting edge. 

How to style oversized t-shirts

When it comes to nailing your oversized t-shirt outfit, there are a number of choices. As the look has grown in popularity there are an increasing number of specifically designed pieces from both designer and straight-to-market brands. However, you can also simply size up on a regular tee for a less dramatic look.

“There are brands that offer oversized t-shirts in their ranges, which means you don’t have to think about it too much, as they’re designed intentionally for an oversized look,” explains Farrah May Archer Boadi, Styling Team Lead at Stitch Fix (opens in new tab). “However if you’re shopping standard t-shirts in a larger size then there are various factors to consider - from body and sleeve length, to shoulder seam and neckline.” 

“The good thing about buying standard t-shirts in different sizes is that you can control just how oversized you go. Cropped t-shirts are a great style to embrace in larger sizes as they will be wider on the body, with longer-length sleeves and a dipped shoulder seam, but, most importantly, the body length won’t overwhelm your frame.” - says Farrah. This tip is especially handy for petites, who can feel swamped in swathes of excess cotton. 

But don't feel limited to your usual brands and categories. 

“It can also be fun to experiment with oversized t-shirts by shopping in the menswear section,” continues Farrah. “A lot of menswear styles aren’t fitted, so they already have a slightly looser fit. Experiment with a few sizes and once you’ve found what menswear size works for you, try French tucking the t-shirt into your jeans and roll up the sleeves for an effortlessly cool look.” Not au fait with a French tuck? It’s a styling trick that involves just tucking the front of your top in and leaving the back out, drawing attention to your waist without the added bulk of a full tuck. This is a great styling trick for all shapes but is also useful for how to style an oversized t-shirt for plus sizes as the gentle half tuck creates more of an hourglass silhouette, skimming your frame whilst lighting contouring. 

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 colorful or patterned blazer, choose a t-shirt in the same hue, or, keep it simple and chic with black or white version beneath. 

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 (one of the biggest fall winter shoe trends 2022). 

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 knee-high 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. “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 color 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 color, fabrication and silhouette of both pieces. 

For daytime, go as oversized as you like with your t-shirt, rolling up the sleeves to exaggerate the effect, and team with wide-leg 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 color 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 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 color t-shirt to wear with a printed or color-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 color, 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. 

Jess Beech is an experienced fashion and beauty editor, with more than eight years experience in the publishing industry. She has written for woman&home, GoodtoKnow, Now, Woman, Woman’s Weekly, Woman’s Own and Chat, and is a former Deputy Fashion & Beauty Editor at Future PLC. A beauty obsessive, Jess has tried everything from cryotherapy to chemical peels (minus the Samantha in Sex and The City-worthy redness) and interviewed experts including Jo Malone and Trinny Woodall.