8 Effortless and Sexy Ways to Wear an Oversize Shirt (Plus One Look That's a Total No-No)

Never frumpy, always flirty

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How to Wear an Oversize Shirt
McKenzie Cordell for PureWow

We’ve said it time and time again: The oversize shirt is a workhorse in our capsule wardrobe. It’s comfy, it’s spacious and it emits a cool nonchalance when styled with with sundresses, cargo pants, trousers, jeans, skirts and countless other pieces. However, billowing button-up shirts can occasionally veer sloppy—especially when proportions are askew—or end up looking like a beach cover-up instead of a wispy, makeshift mini dress. Read on for eight chic ways to wear an oversize shirt that are anything but frumpy, plus one look that’s *so* four years ago. 

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How to Wear an Oversize Shirt: Belt It into a Dress
Getty Images / Rachpoot/Bauer-Griffin

1. Make Like Carrie Bradshaw and Belt It into a Dress

If we learned anything while watching Sex and the City for the umpteenth time, sometimes less is more. Simplify getting dressed by sticking to *only* your oversize button-up shirt, plus a belt at your narrowest part to cinch you in at the waist and keep your impromptu shirtdress from looking like you forgot your pants while running out the door. This look works with every button-down regardless of the print or color. Finish it off with a strappy heeled sandal and tousled, wind-swept hair.

How to Wear an Oversize Shirt: Break Up a Double Denim ‘Fit with a Belt

2. Break Up a Double Denim ‘Fit with a Belt

Paris Fashion Week surprised us with a micro trend we never thought would make its way to the City of Love: Canadian tuxedos. We’re taking a page from their French fashion book and tucking an oversize denim shirt into a pair of straight-leg jeans for a double denim ‘fit that looks well-balanced. You get the billowy sleeves and volume up top from the roomy blouse, plus the slim cut of the pants will make it look like you have legs for days. Don’t forget to break up the sea of denim with a classic, black belt for an elevated, modern look.

How to Wear an Oversize Shirt: Pair an Oversize Button-Down with Other Loose-Fitting Pieces

3. Pair an Oversize Button-Down with Other Loose-Fitting Pieces

Go big or go home with a head-to-toe oversize ensemble. To avoid looking sloppy or like you’re drowning in excess fabric, pay attention to proportion and fit: Consider tucking in half of the button-up into your jeans to highlight your waist and find a jacket with a similar length as your shirt if you can. Lastly, opt for relaxed wide-leg jeans that aren’t too baggy to keep from looking shapeless.

How to Wear an Oversize Shirt: Couple It with Boxer Shorts and Kitten Heels

4. Couple It with Boxer Shorts and Kitten Heels for an Unlikely Blend

For spring, we’re enjoying how carefree an oversize shirt looks when styled with boxer shorts and comfortable kitten heels. Feel free to wear a matching set or add a beachy twist to it by leaving a white button-up shirt undone over a white tank top. Wondering how to add a fashionable flair? Look for colorful heels that will make the casual fit feel dressier.

How to Wear an Oversize Shirt: Tie Your Oversize Shirt in a Knot

5. Tie Your Oversize Shirt in a Knot

When it comes to our oversize shirts, this may be one of the few instances when we want to get things twisted. Loop that excess fabric into a knot just below your chest and watch how you go from drab to fab. The gathering can help pull everything together and even show off a little skin in the process.

How to Wear an Oversize Shirt: Elevate an Otherwise Basic Outfit with Standout Accessories

6. Elevate an Otherwise Basic Outfit with Standout Accessories

We love a tried-and-true uniform just as much as the next person, so we’ll always gravitate to the reliable pairing of an oversize white shirt and blue jeans, especially when the denim has a mid- or low-rise, slouchy fit. To elevate this rather simple pairing, finish off your look with more glamorous accessories like strappy black heels.

How to Wear an Oversize Shirt: Have Fun Mixing Fabrics

7. Have Fun Mixing Fabrics

An oversize button-down in a crisp cotton plays beautifully with contrasting fabrics like leather (or faux leather). Coupling the traditional cloth and structured silhouette of an Oxford shirt with a rock ‘n’ roll-inspired material below creates a fortuitous balance between the soft and grunge, marrying the two opposing fashions rather beautifully. This pairing is a bit of a dark horse, giving you plenty of variations depending on how you style it. For day, dress it down with comfortable sneakers and a work tote bag, then undo a few top buttons and spruce it up with stilettos and a slinky baguette bag for a cheeky nightcap.

Shop Similar Styles

How to Wear an Oversize Shirt: Use a Big Shirt to Lean Into Cowboy Core

8. Use a Big Shirt to Lean Into Cowboy Core

Cowboy boots, mom-fit cut-off denim shorts and an oversize button-up may seem wrong, but we assure you it’s oh-so right. Western-inspired fashion is everywhere right now, thanks to Beyoncé, who sparked the cowboy core craze when she released two singles from her upcoming album, Cowboy Carter. Rustic yet classy, this leggy look feels unexpectedly fresh.

How to Wear an Oversize Shirt Skip An Oversize Shirt with Bike Shorts

One Look to Skip: An Oversize Shirt with Bike Shorts

It seems like just yesterday we were sporting Oxford shirts, bike shorts and dad sneakers, and while we continue to have a soft spot in our hearts (and closets!) for all those pieces individually, we’re no longer wearing them together. Those quarantine days spent in back-to-back Zoom meetings and trudging through at-home workouts are a thing of the past, so we’ll gladly wear any one of the previous outfit ideas in their place.

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Associate Fashion Commerce Editor

Stephanie is a natural savant in the fashion, beauty, and dating & relationships beats. She graduated with a bachelor of arts at the University of San Diego, where she majored...

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