Style Smart: How To Look Chic In An Oversized Shirt

Roomy and ritzy ‘fits ahead

There are many different ways to style an oversized shirt, and yes, it’s possible to look chic and put-together in it despite its roomier fit. Curious to know the not-so-hidden secret behind nailing this fashion woe? Well, it starts with understanding your proportions and playing them to your advantage. Read on as we highlight four fool-proof outfits that you can take style cues from, each one featuring the comfy, oversized shirt. 

The sculptural shirt: Make it the centrepiece of your look

Peek-a-boo, I see you. Stylist, photographer and creative @elkanters snapped a series of artsy self-portraits in a white shirt from Singapore-based fashion label Shirt Number White, which she’s paired with black bottoms. Keeping the focus on the shirt’s origami structure and flared hem, she completed her get-up with just a handful of rings. Note how she’s tucked her hair away neatly to lead the viewer’s attention to the details of her shirt. 

Shirt Number White Origami Shirt, Theory Pleat Skirt and Ancient Greek Sandals

(Left to Right) Shirt Number White Origami Shirt, USD138.04 ( Theory Pleat Skirt in Compact Crepe, ~USD461.88 ( Ancient Greek Sandals 'Celia' Leather Sandals, USD205 (

Style it: When your shirt is this unique and special, you won’t need to do much to make a lasting impression. Let its design speak for itself and keep the rest of your ensemble sleek and simple. Go with a pleated skirt in a dark, solid hue, such as charcoal or black. Then, slide your feet into a pair of black leather sandals with thin straps and you’re all set. 

The bright button-down: Treat it as an overshirt

Bright-coloured button-downs can be tricky to pull off, so you’re prone to committing a fashion faux pas if you were to style them carelessly. If colour blocking isn’t your strongest suit, try wearing only one bright-coloured item and leave the rest of your outfit as neutral-looking as possible. One great example of this is digital creator @shhtephs’ ensemble above, where she layered a “New Bottega”-worthy green button-down over a summery co-ord. For accessories, she went with a shoulder purse and a pair of heeled thong sandals. 

Arket Oversized Linen Shirt, Zara Knit Top with Straps and Zara Straight Jeans

(Left to Right) Arket Oversized Linen Shirt, USD99 ( Zara Knit Top with Straps, ~USD18.40 ( Zara Straight Jeans, ~USD44.27 (

Style it: Not too sure about green? You can consider other colours such as lilac, pink or orange instead. Then, apply @shhtephs’ styling formula by layering the shirt over an off-white outfit. When temperatures dip, you can also loosely tuck the shirt in the jeans and button it up to your chest. 

The blue striped basic: Wear it underneath a blazer

Peep Swedish fashion influencer @matildadjerf’s feed and you’ll quickly see that the wrinkled oversized shirt is part of her everyday style arsenal. In a recent photo she shared on Instagram, Matilda was spotted in a blue striped number with matching boxer shorts. She also restricted the rest of her ensemble’s colour palette to soft beiges and whites. A chic and timeless tribute to ‘90s fashion, don’t you think? 

Hommegirls Striped Cotton-Poplin Shirt, Pomelo Blazer, Axel Arigato Orbit Sneakers

(Left to Right) Hommegirls Striped Cotton-Poplin Shirt, USD231.92 ( Pomelo Sustainable Double Button Fitted Blazer, ~USD47.96 ( Axel Arigato Orbit Sneakers, ~USD213.57 (

Style it: Dust off your corporate button-down and give it a stylish spin by layering it underneath a cream blazer. Balance these heavier layers with a simple white crop top and a pair of cotton shorts to maintain a stylish, laidback vibe. For footwear, go for a pair of lived-in sneakers just like Matilda’s. 

The classic white number: Layer it underneath a corset top

Last but not least, have a go at rocking two separates — the classic oversized white shirt and the corset top — in the same outfit just like Kuwaiti fashion blogger @ascia. Leaving her shirt untucked and unbuttoned makes her get-up even more effortlessly stylish and, dare we say, comfortable too. For bottoms, Ascia went with an equally roomy pair of trousers. Accessories-wise, she brought a little sparkle to her outfit with a few necklaces. 

Cos Oversized Shirt, Dion Lee Panelled Corset Top and By Invite Only Gold Choker

(Left to Right) Cos Oversized Shirt, USD99 ( Dion Lee Panelled Corset Top, ~USD433.80 ( By Invite Only Gold Vermeil Spacer Choker, ~USD87.94 (

Style it: Opt for an oversized shirt that’s not too sheer so that it acts as a solid foundation for the rest of your look. Then, layer a black corset top over the shirt. Ensure the corset is able to cinch your waist snugly so that it helps you to achieve a flattering silhouette instead of making you look frumpy and messy. Dress your neck in a variety of chokers and necklaces to complete your outfit.

Which of the above looks featuring an oversized shirt is your favourite? 

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