How To Wear Oversized Shirts

How To Wear Oversized Shirts


We’re not over oversized shirts - and neither should you be. They’re versatile, easy to wear, and fit for almost anything. We know we don’t need to convince you any further - but you might be wondering the best way to wear an oversized shirt and how to elevate an outfit with one.

Luckily, we’ve got you covered (literally). Although oversized shirts have been a huge trend in recent years, they’re definitely a staple wardrobe piece. We’ll take you through how to wear, what to wear, and when to wear this perfect accompaniment to your capsule wardrobe.

The smart oversized look

We love casual as much as anyone else, but when it comes to making an impact, you don’t always have to sacrifice comfort for style and sophistication. An oversized shirt or baggy T can be dressed up easily (often with pieces already in your wardrobe).

Oversized meets oversized when you team a blazer and t-shirt. Matching neutral colours can really elevate a look (think Kim Kardashian pre-Pete Davidson), especially when teamed with heavy biker boots, or a dangerously high heel. Belted at the waist and plenty of gold jewellery, this is a look that will get heads turning.

If you don’t fancy layering your oversized pieces, a belted oversized shirt will look just as sophisticated - and is actually a really key look for the office. Team with thick tights and knee-high boots in the winter, as well as a colourful beanie - and then take the look into the warmer months. Summer will look more like chunky platform sandals and maybe a straw hat, if you’re feeling fancy.

The casual but chic look

Oversized shirts and t-shirts make the perfect outfit on their own. No bells and whistles with this little (large) number, literally accompany it with your favourite pair of trainers or hi-tops - but don’t forget to wear a big pair of knickers too (or don’t, who are we to judge!?).

Jewellery and accessories can then give your oversized shirt that oomph it might be needing, without much effort. We’re thinking of huge hoops, tiny bags, and plenty of attitude.

The classic 90s look

We never thought we’d be using the words ‘classic’ and ‘nineties’ in the same sentence, but here we are. 90s fashion has made a real comeback in the 2020s, with style icons such as Princess Diana and Jennifer Aniston (okay okay, Rachel from Friends) giving us the inspiration we crave for casual, chic looks.

And for the oversized shirt, it may have had a moment in the 90s, but that’s certainly been revived. Team with cycling shorts and chunky trainers for a classic outfit that can take you from the gym to brunch with the girls. It’s our go-to for a quick, but effective evening outfit too. Style with chunky gold jewellery, sleek bun, and sky-high stilettos, and you won’t even feel like you’ve dressed down.

The don’t mess with me look

Wearing an oversized t-shirt takes an oversized attitude - especially when paired with biker boots and a look that could kill. Add a leather or pleather jacket into the mix and you’ve got the perfect outfit for when you mean business.

We all know that Kim K has got the oversized T look down - as well as the don’t mess with me attitude. She keeps it simple with chunky chokers and equally chunky trainers. Try maintaining the same colour scheme throughout this look to really make an impact.

The stay out late look

Tucked in or out, the oversized shirt works. For our stay out late look, try with a mini skirt or layered over a slip dress. This might not be your usual style, but it’s definitely Rihanna’s - and who are we to argue with Rihanna?

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