It seems like it just yesterday the golden age of baggy clothes began. People have long been trading in their tailored and fitted looks for clothes with a bit more volume and space to accommodate our style needs. While the origins of oversized clothing can be dated back to Ancient Rome with the invention of the toga, or parts of South Asia with the loose-fitting kurta, oversized garments have been essential since pretty much forever. For this reason, it’s time to show some love to the oversized shirt and all it’s baggy glory.

Before it became a mainstream trend during the early ‘90s, baggy clothes were an expressive way to rebel against the tight-fitting track suits and kangol bucket hats of the ‘80s. Brands like Polo and Coogi grew to prominence and still hold an important place in streetwear to this day.

Fast forward to now, more than thirty years later oversized shirts remain a staple in the streetwear community and have been co-opted by luxury fashion houses as well. One look at Balenciaga or Louis Vuitton’s catalogue and you’ll see how baggy fits have become seasonal items in more ways than one.

Simply throwing on an oversized shirt with any outfit won’t do — you’ve got to carefully consider the proportions of the rest of your ‘fit too. Over the years we’ve seen countless ‘dad fits’ from Adam Sandler with his wide array of baggy shirts, to Rihanna opting for an oversized shirt for a dinner date with A$AP Rocky.

Regardless of your gender, there’s a way to style oversized shirts that fits with the clothes you already have in closet. Pair it with some loose or relaxed pants, or opt for a complete fit like Justin Beiber and bask in your baggy glory. We've rounded up some of out favorite oversized shirts from workwear-inspired luxury options by Visvim to contemporary classics from Urban Outfitters.

Cop the best oversized shirts below

Diomene by Damir Doma Button-Down Overshirt

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Button-Down Overshirt


Diomene by Damir Doma

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Diomene’s Overshirt makes it easy to achieve a baggy ‘fit as the shirt is already cut largely for a comfortable and cozy overall look. Small details like the monochrome embroidery on the left sleeve and the button down collar will set you apart for seasons to come.

Visvim Contrary Dept Wallis Shirt

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Contrary Dept Wallis Shirt



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Visvim’s catalogue, specifically its CONTRARY DEPT has often blurred the lines between military-inspired workwear and comfy lifestyle options. For those that can appreciate quality in products that last, this all-over graphic print shirt is one of a kind.

Kenzo Boke Flower Crest Overshirt

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Boke Flower Crest Overshirt



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Overshirts are essential for those days when the weather is a bit uncertain, but also work really well when paired with a nice tee underneath. Kenzo’s offering, seen here embroidered with its boke flower logo is truly versatile for any formal or idle situation.

Urban Outfitters UO Marc Oversized Oxford Shirt

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Oversized Oxford Shirt


Urban Outfitters

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When the model pictured is over six feet tall and wearing a medium you’ve truly stepped into oversized territory. UO save you the guess work and sizes up its classic Oxford shirt so you look as comfortable as you feel.

Acne Studios Plaid Shirt

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Plaid Shirt


Acne Studios

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Acne sticks to the basics for its Plaid Shirt made with oversized connoisseurs in mind. The brown and grey color pattern is just Iin time for autumn, and if you want folks to know you’re wearing Acne, simply make use of the shirt’s front pocket.

GmbH Tahir Twill Tartan Shirt

Tahir Twill Tartan Shirt



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While most folks might know GmbH for its club-ready apparel, the brand is well-versed in producing lifestyle wear from deadstock fabrics too. This large flannel is perfect for seasonal layering and comes with reinforced sleeves, guaranteeing you’ll keep it in your wardrobe for as long as you like.

Maison Margiela Décortiqué Oxford Shirt White

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Décortiqué Oxford Shirt


Maison Margiela

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Margiela’s Décortiqué Oxford Shirt is a fitting example of how luxurious baggy looks when done well. No frills, no extra gimmicks or stitching, just a quality oversized shirt you can wear in any setting.

OrSlow Convertible-Collar Shirt

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Cotton-Chambray Shirt



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OrSlow cuts out the middle men and emissions by locally sourcing the fabrics and artisans used for its products from Japan. Although the shirt is made in a relaxed fit, I'd recommend sizing up for a loose feel.

Highsnobiety Rayon Short-Sleeve Shirt

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Rayon Short-Sleeve Shirt



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Our Rayon Shirt is ideal for those warm days when you’re taking it easy and can be worn throughout the year or paired with a long sleeve underneath. Made in a boxy fit with embroidery on the pocket, I’d recommend sizing up for proper oversized proportions.

Standard Cloth Ellis Relaxed Dress Shirt

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Ellis Relaxed Dress Shirt


Standard Cloth

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Standard Cloth's Relaxed Dress Shirt is one of those items that just stays in your rotation simply because you can pair it with anything. Whether you’re wearing it to work or for a casual outing, the drapey silhouette is a timeless choice.

Pop Trading Company Pop BD Shirt

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Pop BD Shirt


Pop Trading Co.

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It’s been long understood that (some) skaters have great style, and naturally the ones that do venture in fashion or start brands themselves like Pop Trading Company. Aside from the low key embroidery towards the waist, the BD Shirt feature an extra-large pocket on the chest which arguably makes the shirt more oversized than the rest.

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