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

Button-Down Overshirt

Button-Down Overshirt

$420

Diomene by Damir Doma

Buy at Highsnobiety

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

Contrary Dept Wallis Shirt

Contrary Dept Wallis Shirt

$590

visvim

Buy at Slam Jam

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

Boke Flower Crest Overshirt

Boke Flower Crest Overshirt

$390

KENZO

Buy at Highsnobiety

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

Oversized Oxford Shirt

Oversized Oxford Shirt

$59

Urban Outfitters

Buy at Urban Outfitters

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

Plaid Shirt

Plaid Shirt

$230

Acne Studios

Buy at ssense

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

$280

GmbH

Buy at Highsnobiety

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

Décortiqué Oxford Shirt

Décortiqué Oxford Shirt

$720

Maison Margiela

Buy at Slam Jam

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

Cotton-Chambray Shirt

Cotton-Chambray Shirt

$290

OrSlow

Buy at Mr Porter

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

Rayon Short-Sleeve Shirt

Rayon Short-Sleeve Shirt

$84

Highsnobiety

Buy at Highsnobiety

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

Ellis Relaxed Dress Shirt

Ellis Relaxed Dress Shirt

$69

Standard Cloth

Buy at Urban Outfitters

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

Pop BD Shirt

Pop BD Shirt

$140

Pop Trading Co.

Buy at Pop Trading Co.

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.

Want to keep browsing? Head to the Highsnobiety Shop for more products that we love. Highsnobiety has affiliate marketing partnerships, which means we may receive a commission from your purchase.

What To Read Next

  • Image on Highsnobiety

    At Bally SS23, Rhuigi Villaseñor Strikes Gold

    Style
  • Image on Highsnobiety

    Leave It to A$AP Rocky to Make the Western Tuxedo Look Cool

    Style
  • Image on Highsnobiety

    Bottega Veneta SS23 Is Full of Moods

    Style
  • Image on Highsnobiety

    HAL STUDIOS & ASICS Go Forest Mode

    Sneakers
  • Image on Highsnobiety

    Ferragamo Enters Its Sexy Era Under Maximilian Davis

    Style
  • Image on Highsnobiety

    All Things Julia Fox at Highsnobiety's Milan Fashion Week Party

    Culture
*If you submitted your e-mail address and placed an order, we may use your e-mail address to inform you regularly about similar products without prior explicit consent. You can object to the use of your e-mail address for this purpose at any time without incurring any costs other than the transmission costs according to the basic tariffs. Each newsletter contains an unsubscribe link. Alternatively, you can object to receiving the newsletter at any time by sending an e-mail to info@highsnobiety.com

Web Accessibility Statement

Titelmedia (Highsnobiety), is committed to facilitating and improving the accessibility and usability of its Website, www.highsnobiety.com. Titelmedia strives to ensure that its Website services and content are accessible to persons with disabilities including users of screen reader technology. To accomplish this, Titelmedia has engaged UsableNet Inc, a leading web accessibility consultant to help test, remediate and maintain our Website in-line with the Web Content Accessibility Guidelines (WCAG), which also bring the Website into conformance with the Americans with Disabilities Act of 1990.

Disclaimer

Please be aware that our efforts to maintain accessibility and usability are ongoing. While we strive to make the Website as accessible as possible some issues can be encountered by different assistive technology as the range of assistive technology is wide and varied.

Contact Us

If, at any time, you have specific questions or concerns about the accessibility of any particular webpage on this Website, please contact us at accessibility@highsnobiety.com, +49 (0)30 235 908 500. If you do encounter an accessibility issue, please be sure to specify the web page and nature of the issue in your email and/or phone call, and we will make all reasonable efforts to make that page or the information contained therein accessible for you.