Figuring out how to style an oversized button-up shirt will unlock so many outfits. Take it from someone whose wardrobe includes a full collection of button-downs in a whole variety of colours. This should come as no surprise, since fashion editors and French girls alike have long sworn by the magic of a classic collared top. It’s one of the key capsule wardrobe building blocks, and it can transform even the simplest warm-weather outfits into polished, head-turning looks.
What makes a button-down shirt (a slouchy one, especially) a timeless winner is its ability to look put-together while feeling so easy, like you're wearing nothing. No matter your personal style or fit of choice — slightly relaxed, totally baggy, or anywhere in between — these shirts are way more versatile than you’d think. Lounging at home, heading to the office, sipping an afternoon spritz… these light, sophisticated layers do, in fact, go with everything.
Here are six different ways to style an oversized shirt for any occasion.
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From morning meetings to happy hour
It doesn’t get more ’90s office-core than a crisp button-up and a form-fitting pencil skirt. This street-style-approved outfit combo balances the best of both worlds: a masculine white shirt with a feminine midi. We’re all for playing into the look that would command the office just as much as it would a front row at a fashion show. No need to overthink it – a minimalist pair of sandals and your favourite handbag will do the trick, and let your confidence take over.
Styling tip: Head to the office with your shirt layered underneath an equally oversized jumper – or throw on a blazer with rolled sleeves.
On a coffee date
A last-minute hangout calls for an outfit that requires zero effort, especially if you find yourself in a rush. Leave extra room for the commute by sticking to what you know works: Leave your button-down open and untucked, layering a basic T-shirt or tank top underneath. A pair of wide-leg jeans and ballet flats will never fail you. Plus, in flats, you’ll be able to reach your destination in comfort and style.
Styling tip: Let your loose-fitting top do the work and wear it partially tucked into a pair of jeans to emphasise your shape—or go rogue (in this case, untucked and unbuttoned) for brunch with friends.
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For a relaxed approach that’s always on-trend for the in-between seasons, style your oversized button-down with a chunky leather jacket. While I do love a baggy-on-baggy look, I’ll actually recommend playing with proportions here by opting for straight-leg or skinny trousers and some statement shoes for a well-balanced, polished feel. A pair of sleek Mary Janes will do just the trick.
Styling tip: This outfit also works well without the layer, meaning you can wear it all the way into summer—just roll up the sleeves or even tie it around your waist when things heat up.
When I say business casual, I don’t mean stuffy work clothes. Breathe new life into the preppy aesthetic by pairing your tailored blazer with a ribbed tee and your go-to pair of jeans. As for the button-up shirt, I’m all for an element of surprise. Throw it on over your shoulders or belted at the waist for an unexpected accent that puts all the emphasis on the casual, but still remains effortlessly stylish.
Styling tip: To dress it up a bit, swap the jeans for roomy slacks. On the weekends, throw on some slim, ballet trainers to keep your look feeling more grounded.
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Whether you’re heading out to run some errands, the office, or an after-hours gathering, let your outfit be the least of your worries. A billowy, button-down shirt pairs beautifully when tucked into an unexpected trouser silhouette like cargo pants – I speak from experience. Add workwear essentials like kitten heels and a structured handbag, making the ensemble ideal for meetings that transition seamlessly into the evening.
Styling tip: If you’ll be walking a lot during your odyssey of a day, flats also work perfectly here; decide between loafers for polished looks or sneakers for guaranteed comfort.
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There’s nothing that feels as timeless as a blouse and skirt for date night. To prime your oversized button-down for a special occasion, here’s a reliable hack: half-tuck the shirt into your skirt of choice. My favourite option? Well, it's safe to say you can never go wrong with a leather skirt. Accessorise your look with sandals or kitten heels, and throw on a chic purse. Sunglasses are optional, but highly recommended.
Styling tip: Throw on a trench coat for chilly evenings, or sub in a satin midi on warmer nights. This also makes a winning holiday look, just saying.
A version of this article originally appeared in Glamour US.
