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How To Style Oversized Shirts Like a Star in 2024

A quick glance at the current fashion trends is sufficient to confirm what fashion insiders have known all along: oversized shirts are the fastest ticket to envy-inducing street style. The ultimate weapon in the lazy girl’s wardrobe for casual chic, there are endless ways to wear this staple from vintage graphic tees to the classic button-down.

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Photo: Getty

For further proof, look no further than the current crop of sartorial savants for cues on styling oversized shirts for women. Margot Robbie has the last word on street style inspiration with her striped button-down and baggy jeans, while Zendaya loves accessorizing her oversized shirts with a belt at the waist and classic black pumps. Looking to skip the usual suspects? Anne Hathaway served up a dose of sunshine with a floor-grazing oversized yellow shirt and the most unexpected finishing touch: a statement diamond necklace. 

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Ready to get started? From the trendy oversized shirt looks to bookmark to layering tips and DIY fashion hacks, here’s all that you need to know. 

How can I style an oversized shirt for a casual look?

  • Fret not, this is a common question for those who want to lean in to the style mileage of this effortless staple while still looking like they have put in an effort.
  • If you are just getting started with the possibilities of an oversized shirt, it helps to play it safe by sticking to classics. 
  • A failsafe striped shirt makes for the wardrobe investment that will pay itself off infinite times over, whether you are teaming it with vintage denims or wearing it as a minidress with white sneakers.
  • Another styling hack includes slipping a few buttons open at the top and slipping out a shoulder for an insouciant finish. 

Catherine striped oversized shirt, Anine Bing

How to style an oversized shirt and shorts?

  • Once you have mastered the basics and are ready to level up, the next module on oversized shirts is dedicated to playing with proportions. 
  • If you have an on-the-go lifestyle, opting for a half-tuck with your go-to pair of shorts will deliver that effortless laidback appeal. Roll up the cuffs, leave a few buttons undone and you’ll be golden. 
  • Or if you have been wondering how to style an oversized shirt with denim shorts, you can always reach for light layers—such as a long button-down or shrug—to pull the look together. 
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Triangle logo oversized t-shirt in cotton jersey, Prada


Bite logo shorts in denim, Alexander Wang.T

How to style an oversized shirt with leggings?

  • Whether you are looking to nail the memo on athleisure or like to make heads turn your way while you dash to the gym, leggings are an inseparable mainstay of every wardrobe. 
  • For bringing about the merry union of these two lazy girl staples, it helps to turn your focus on your silhouette. 
  • Play with opposites by pulling an oversized tee over a pair of fitted leggings as you hit the juice bar after the gym. 
  • If you are looking for a more put-together look, a common styling hack for oversized shirts is to cinch it at the waist with a belt. 
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Hooded sweatshirt in cotton jersey, Valentino Garavani


Silverstone full length leggings in recycled polyester, P. E. Nation

How to style an oversized shirt with sweatpants?

  • The go-with-anything appeal of oversized shirts further proves its mettle when paired with sweatpants. 
  • For a weekend-ready look, be prepared to fully commit to the memo: pair your favorite oversized tee with graphic trackpants and add in Y2K-approved candy-coated jewelry. 
  • For the minimalists at heart, an all-white tee makes for a merry companion with monochromatic sweatpants and statement sneakers. Layer the look with a bomber jacket and you are good to go. 

Logo oversized crop top in cotton jersey, Miu Miu


Flocked DG logo-print sweatpants in cotton-jersey, Dolce & Gabbana

How to style an oversized shirt dress?

  • If you are looking to go down the no-fuss route with oversized silhouettes, a shirtdress is the easiest way to master this staple. 
  • The ultimate one-and-done weapon in the busy girl’s wardrobe, this silhouette doesn’t require much by way of accessorizing but you can choose to team it with a classic black handbag, chain link necklace and sleek sunnies for a polished look. 
  • On nights when you are looking to add some drama to your look, this silhouette can be easily teamed with over-the-knee boots for date nights. 
  • If you’d like to flex your sartorial muscles, oversized shirtdresses can also be worn unbuttoned over a classic white-tank-and-denims duet or tucked into a midi skirt for an office-ready look.  

Lena mini shirtdress in linen, Morton Mac

What accessories complement oversized shirts for women?

  • Once you have mastered the styling possibilities of oversized shirts, it is time to turn your attention to the accessories that they can be paired with. 
  • For those who favor sleek, polished looks, it helps to maintain fidelity to failsafe classics that can withstand the test of time and the onslaught of flash-in-the-pan trends.
  • Your choices include—but aren’t restricted to—patent leather pumps, cat-eye sunglasses and the holy grail of all finishing touches: a pair of gold hoops. 

Signature chain hoop earrings, Coach


Double C cat-eye sunglasses in recycled acetate, Cartier


Rockstud bow slingback pumps in patent leather, Valentino Garavani

What footwear goes well with oversized shirts?

  • The styling capabilities of a classic pair of white sneakers was never in question but you can put them to the test by pairing them with just about every iteration of oversized shirts. 
  • Knotting a relaxed tee over high-waisted shorts? Wearing this casual silhouette as a dress? Layering it under a bomber jacket and rounding off with casual joggers? There are scarcely any styling scenarios that a pair of white sneakers cannot do justice to. 
  • Other candidates commonly include Birkenstocks, chunky wedges or the internet’s newest obsession with layering socks with sandals. 

Air Force 1 ’07 sneakers in leather, Nike

Whether worn as it is or layered up for fall with a turtleneck underneath or made office-ready with tailored outerwear, the styling possibilities for an oversized shirt are endless. Make note: you heard it here first!

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