How to wear oversized shirts for an effortless everyday look

Here's how to wear oversized shirts for day, play, summer and winter according to the stylists in the know.

street style models showing how to wear oversized shirts
(Image credit: Getty)

Want to know how to wear oversized shirts without feeling like you’re being overwhelmed by fabric? You’re in the right place.

Pieces you can throw on at a moment's notice are always the ones that earn their keep in your wardrobe, and an oversized shirt definitely falls into that category. The breezy shape has the benefit of being both roomy and comfortable, while the crisp collar and cuffs will make any outfit feel polished and put together.

To max out your cost-per-wear, opt for an oversized shirt in a neutral, goes-with-anything hue like white or pale blue. These neutral shades can then be easily mixed and matched in your wardrobe—tucked into your best jeans and worn open layered over your best dresses. These classic shades will lean into the borrowed-from-the-boys aesthetic too, playing on the shirt’s androgynous features. 

So, just how oversized should you go? “I’d say this depends on your height and frame, as well as the style you want to achieve and the occasion you’re shopping for,” explains Katie Eastwood, Stylist Ambassador at Stitch Fix UK (opens in new tab). How the proportions of your oversized shirt compare to the rest of your outfit is important too. “There should always be something slim on show whether an ankle, a waist or shoulders,” advises Rachel Ingram, Editor in Chief at Threads Styling (opens in new tab). “For example pairing an oversized shirt with denim shorts and bare legs, or an oversized T-shirt tucked neatly into a high waist trouser. You want to show body shape beneath the bagginess.”

Helpfully, some shirts are listed as “oversized”, so you can buy your usual size with confidence. They’ll be a little bigger than normal, but still have taken the proportions of your body shape into consideration. Buying a couple of sizes larger in a regular shirt, or even shopping in the mens department are both options too, but keep in mind that they haven’t been designed with your frame in mind. 

“It’s always worth a look in the mens section if you can’t find anything you like in the women’s department, but it’s also worth remembering how sizes differ—men’s shirts will be made for different body types, so they may be bigger in the shoulders for example, and won’t take into account the female form,” says Katie Eastwood. They’re often bigger on the collar too. “A nice way to wear a men’s shirt is to wear it as a light layer—over a strappy top and jeans, to act as a shacket for when the sun dips.”

How to wear oversized shirts

Despite oversize shirts being very popular, they don't always feel easy to wear. We breakdown how to style them for different seasons and occasions. 

How to wear oversized shirts for day

street style influencers showing how to wear oversized shirts for day

(Image credit: Getty)

“Oversized shirts are one of my core capsule wardrobe staples,” says Ella Gaskell, celebrity stylist and founder of P.S. Online Styling (opens in new tab). “My favourite way to wear an oversized shirt for daytime is to wear it untucked and open over a tank top, with the bottom two buttons done up. I then tuck the front into jeans which instantly gives it a bit of shape, but yet it hangs down and feels slightly ‘undone’.” Alternatively, you could leave the buttons altogether, wearing your oversized shirt more like this season’s “shacket” - that’s a cross between a shirt and a jacket for the uninitiated.

“One of my favourite looks is to pair a plain colored or striped shirt with some loose-fitting, tailored trousers,” adds Katie Eastwood. “Deliberately (but stylishly) oversized, this is not only a really chic look, but super comfortable too—perfect for your post—lockdown office wardrobe.” Just add box fresh white trainers, your best sandals and a pair of statement sunglasses

How to wear oversized shirts for evening

street style influencers showing how to wear oversized shirts for evening

(Image credit: Getty)

An oversized shirt has the potential to take your outfit from day to night with minimal adjustments and just a few extra accessories. Katie Eastwood recommends adding “statement jewellery, a pair of heels or a bold lipstick” to your classic shirt and blue jeans combination to make it feel more evening-appropriate. If you’re going somewhere with a no denim policy, swap your jeans for high-shine leggings, tapered faux leather trousers or a slinky midi skirt instead. 

“Depending on the event and the proportions of the bottom half of your outfit, I would give the shirt a “french tuck”,” says style consultant Charlotte Verdeyen. This means tucking in your shirt at the front only, leaving the back loose. This will draw attention to your middle and give your frame definition, without losing the relaxed feel. Keep your hair simple - tied back or swept to the side - to put the focus on the collar, and finish your outfit with a chic leather blazer or biker worn draped across your shoulders. 

Kurt Geiger London Pierra sandal: £129 | Kurt Geiger (opens in new tab)

Sponsored

These strappy heels would be a great addition to any evening outfit featuring an oversized shirt. The multicoloured rainbow design of this shoe will add a major wow-factor to your outfit while the dainty straps with studded buckles introduce a touch of glamour. Pair these with an oversized shirt tucked into a pair of mom jeans (opens in new tab) for the ultimate evening look.

How to wear oversized shirts in winter

street style influencers showing how to wear oversized shirts in winter

(Image credit: Getty)

The stand-out features of an oversized shirt make them great for layering when the weather turns. Instead of using yours purely for warmth, make a statement by letting the collar or cuffs peek out beneath a slouchy knit or tailored jacket. The crisp cotton will contrast beautifully with chunky wool or fuzzy faux fur. If your oversized shirt is made from a heavier fabric, like flannel or corduroy, you could even use it as outerwear, buttoned up and layered over a fine knit jumper or long-sleeved top. 

As for colors, this season’s clothing trends predict a commitment to rich, earthy reds and browns, alongside biscuit and caramel-hued beiges. Oversized shirts in these shades will serve you well through the colder months, or, if you don’t want to invest, your trusty white or blue shirt will coordinate with trousers or skirts in any of these colorways. 

How to wear oversized shirts in summer

street style influencers showing how to wear oversized shirts in summer

(Image credit: Getty)

Incredibly versatile, the question of how to wear oversized shirts applies just as much to the summer months as it does the colder ones. Now’s the time to really think outside the box, instead of limiting your oversized shirt to just being worn with jeans. 

“On a warmer day, you can replicate the same look as with your jeans, but with a pair of denim shorts instead,” says Katie Eastwood. “This is also a great opportunity to add a pop of colour, by pairing your denim cut-offs with a bright button-up.” Sunset shades of pink, red and orange are all gorgeous choices for during the summer months, while icy blue and white will really show off your tan.

“Another option is to try the dress technique—shop a shirt in a few sizes above and wear it as a summer evening dress, paired with sandals, trainers, or heels,” continues Katie. “It’s a lovely look for a warm summer’s evening. For those that like to accentuate their waist, the addition of a belt can be a really magic touch here too.”

If you’re lucky enough to be heading to sunnier climes, cut down on packing by using your oversized shirt as a beach cover-up. “Throw yours over a stunning piece of swimwear, add a classic straw sun hat, a big chunky necklace and a cocktail,” advises Charlotte.

Kurt Geiger London Meena Eagle Slider: £99 | Kurt Geiger (opens in new tab)

Sponsored

Finish off any casual daytime oversized shirt outfit with these glam sliders that feature a quilted strap for a luxe look. The curved outsole means that these will support your feet and keep your comfortable while you're out and about walking around while giving you a trendy appearance at the same time. And the brand's staple eagle embellishment adds an extra touch of high-fashion.

Best oversized shirts to shop now

& Other Stories Oversized Linen Shirt

(Image credit: & Other Stories)
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Specifications

RRP: $89/£65
Sizes: XS-L

Reasons to buy

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Side vents for a flattering cut
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Pretty pastel colour way 

Uniqlo Linen Blend Short Sleeved Long Shirt

(Image credit: Uniqlo)

Uniqlo Linen Blend Short Sleeved Long Shirt

Specifications

RRP: $35/£24.90
Sizes: XS-XL

Reasons to buy

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Short sleeves great for layering
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Neutral shade 

H&M Oversized Linen-Blend Shirt

(Image credit: H&M)
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H&M Oversized Linen-Blend Shirt

Specifications

RRP: $34.99/£24.99
Sizes: XS-XXL

Reasons to buy

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Eye-catching print
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Chest pocket 

Zara Striped Poplin Shirt

(Image credit: Zara)
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Zara Striped Poplin Shirt

Specifications

RRP: $39.90/£25.99
Sizes: XS-XL

Reasons to buy

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Bold statement cuffs
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Goes-with-anything stripes 

Mango Oversize Poplin Shirt

(Image credit: Mango)
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Mango Oversize Poplin Shirt

Specifications

RRP: $49.99/£29.99
Sizes: US: 2-10/UK: 6-14

Reasons to buy

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On-trend shade
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Flattering asymmetric length 

M&S Collection Pure Linen Oversized Long Sleeve Shirt

(Image credit: M&S)
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M&S Collection Pure Linen Oversized Long Sleeve Shirt

Specifications

RRP: $50/£29.50
Sizes: US: 2-20 / UK: 6-24

Reasons to buy

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Made from 100% linen
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Classic shape 

Boden Hannah Linen Shirt

(Image credit: Boden)
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Boden Hannah Linen Shirt

Specifications

RRP: $110/£75
Sizes: US: 2-22/UK: 6-26

Reasons to buy

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Available in a wide range of colours
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Flattering V neckline

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.