How to style oversized shirts for every occasion

Wondering how to style oversized shirts without looking overwhelmed by fabric? This is how to wear them according to fashion experts

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

Pieces you can throw on and go 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 get maximum cost-per-wear, opt for an oversized shirt in a neutral, goes-with-anything hue like white or pale blue. Neutral shades can then be easily mixed and matched with other items, tucked into jeans and worn open layered over dresses. 

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).

Consider the proportions of your shirt compared to the rest of your look. You still want to highlight your shape - whether that's your waist, or an ankle, but maintaining an area of your silhouette will stop you looking overwhelmed in fabric.

“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.” advises Rachel Ingram, Editor in Chief at Threads Styling

How to style oversized shirts

Despite being 'oversized', the look is actually highly managed with proportions well-considered. Many shirts are purposefully leaning into this aesthetic, and are listed as 'oversized', meaning you can buy your usual size and still achieve the look. They’ll be bigger than normal, but still have taken the proportions of your body shape into consideration.  

“It’s always worth a look in the men's section (too) 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.”

Here's how to style oversized shirts for all occasions. 

1. How to style oversized shirts for day

street style influencers showing how to wear oversized shirts for day

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“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 favorite 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.

“Pair a plain colored or striped shirt with some loose-fitting, tailored trousers,” adds Katie Eastwood. “Deliberately oversized, is not only a really chic look, but super comfortable too.” Just add box fresh white trainers, or your best sandals and a pair of the best sunglasses and you're good to go. 

2. How to style oversized shirts for evening

street style influencers showing how to wear oversized shirts for evening

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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 jewelry, 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, or use it as an exercise in how to style leather pants 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 (opens in new tab)

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. 

3. How to style oversized shirts in summer

street style influencers showing how to wear oversized shirts in summer

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"This is also a great opportunity to add a pop of colour, by pairing your denim cut-offs with a bright button-up,” says Katie Eastwood. 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. Similarly with trousers, try a half tuck of your shirt into a pair of shorts or denim cut-offs for a beach-ready look.

“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 nailing how to wear oversized shirts as the best beach cover ups and embrace this season's obsession with the Coastal Grandmother trend, for effortless beachside style. “Throw yours over a stunning piece of swimwear, add a classic straw sun hat, a big chunky necklace and a cocktail,” advises Charlotte.

4. How to style oversized shirts in fall

street style influencers showing how to wear oversized shirts in winter

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When it comes to how to style oversized shirts, it's the standout features that make them great for layering when the weather turns. Instead of using yours purely for warmth, make a statement by letting the collar and/or cuffs peek out beneath a slouchy knit or tailored jacket. The crisp cotton will contrast beautifully with chunky wool or fuzzy faux fur too. If you're looking for to style oversized shirts 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, transforming it into a shacket. 

As for colors, this season’s fall 2022 fashion 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. 

Best oversized shirts to shop now

Jess Beech

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.

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