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How to Style an Oversized Shirt

Button-down shirts come in a variety of shapes, sizes, prints, and fabrics. They can be a basic white shirt that is your office go-to, or of the frilly floral variety for an evening out. This season, the oversized version seems to be on trend, and while you might think there’s only one way to wear a shirt, you may be surprised that a few styling tricks can transform this basic wardrobe staple into a stylish look.

First up, layering. It’s easy to get lost in a larger shirt, which is why layering it with tailored outerwear can be a simple way to add structure to your overall outfit. Outerwear can include a trench coat, a blazer, a vest, or a denim jacket. When layering outerwear with a button-down, you want a bit of zhuzhing. So, definitely pull out the cuffs and do some rolling and tucking of the sleeves on your outerwear, and just out the collar of the shirt. You don’t need to meticulously flip and fold over the collar; just have it peek out a bit.

Also consider under layers. An oversized shirt, especially if sporting a striped print like Quince’s 100% Organic Cotton Poplin Long Sleeve Shirt in light blue stripe, adds texture and visual interest. Wear it with the hem tied up over a solid-colored shift dress or tuck it into black straight-leg pants and layer over a black turtleneck.

I also like the idea of pairing an oversized button-down with unexpected pieces like athletic or leisure wear. Try a white, borrowed-from-the-boys shirt half-tucked into a pair of track pants like Walmart’s No Boundaries Track Pants in classic red, throw a navy sweater around your shoulders, and finish the look with white sneakers and a ballcap for weekend errands. Or utilize a big button-down as a workout cover-up over leggings and a sports tank.

You can also attempt to elevate more casual pieces with a button-down. Take Uniqlo’s Crepe Jersey Boat Neck T-shirt and matching Straight Pants, layer a button-down underneath the sleeveless tee, and pair with loafers for an easy-breezy office look.

Or, for an evening out, pair a button-down over a jumpsuit like Dick’s Calia Women’s Jersey Jumpsuit, tie up the tails, or try an askew buttoning and wear with flats or heels and gold jewelry.

Speaking of “askew buttoning,” there are a ton of tutorials online on how to alternatively button or fasten an oversized shirt to achieve various silhouettes. There are even tricks that utilize hair-ties to create wrap and cropped allusions. I’m not going to try and type out the mechanics of these methods, but I advise watching these reels and videos in slow motion, with your shirt on, in front of a mirror, and pause as needed to achieve various style hacks when it comes to oversized shirts.

I can address tucking and recommend experimenting with full-tucks, half-tucks, and French-tucks when wearing an oversized shirt. Basically, with any tuck, you want to fluff out the shirt and consider uneven tails for a front tuck. You can also find how-to videos on these as well, but you can probably achieve whatever dimensions you find most flattering through trial and error.

And speaking of dimension, try playing with proportions when styling oversized shirts. If you have a lot of volume up top, you’ll want to balance that on the bottom. There are two approaches to achieve this balance: first, a more fitted pant, skirt, or short. I love the look of a long Bermuda short, like J.Crew’s 9” Pleated Heritage chino short with knee-high boots and a button-down. The second option is to match volume with volume, but cinch in the middle. Pair an oversized shirt with flared or wide-leg pants, like Loft’s Faux Leather Buckel Wide Leg Corduroy Pants. The built-in buckle feature creates the “cinch” when the shirt is tucked, whether partially or fully, to create an hourglass effect. Of course, any wider pant with belt loops and a belt can also achieve this volume balance.

Another stylish aspect of oversized shirts are statement cuffs. You can look for the traditional white cuff, like Old Navy’s Oversized Button-Down Boyfriend shirt in navy stripe with a matching white collar, and play around with zhuzhing. Wear it with jeans and a sweatshirt for a casual look. Or go for some drama with Commense’s Pleated Cuff Collar Tied Button shirt that, as the name indicates, has a pleated and flared cuffs perfect for peeking out of a cardigan or blazer. This definitely has a luxe feel, so I would pair this with a rich fabric like velvet or stain.

Lastly, accessories. Wearing oversized shirts may tend to look a bit sloppy, especially when worn loose and untucked with more casual pieces like track pants and jeans. To amp up the style factor while still feeling comfortable, try accessorizing with chic closet staples like simplistic handbags, a sleek pair of sunglasses, gold jewelry, and unscuffed shoes.