Bigger is Better: The Best Oversized Shirts to Wear this Fall
It seems like it just yesterday the golden age of oversized shirts and 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 its baggy glory.
Before it became a mainstream trend during the early ‘90s, oversized shirts were an expressive way to rebel against the tight-fitting tracksuits 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 catalog 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 fit with the clothes you already have in your closet.
We've rounded up some of our favorite oversized shirts from workwear-inspired luxury options to contemporary classics.
Cop the best oversized shirts for this fall below.
Jean Paul Gualtier - Poplin Tie Shirt
This Jean Paul Gaultier oversized button-down comes with a matching tie and a contrasting JPG screenprint. The shirt is made in Italy from 100% cotton and cut for a loose fit at hip length. Definitely one of those statement oversized shirts for your fall outfits.
Lemaire - Souble Pockert Shirt
The Double Pocket Shirt is a newer Lemaire style that brings some comfort and a relaxed look to an essential oversized short-sleeve shirt. Crafted from a cotton-nylon blend fabric and outfitted with mother-of-pearl buttons that line down the center front, this shirt has all the features to be a fall staple in your wardrobe.
Y/Project - Evergreen Shirt
Since the appointment of Glenn Martens as Creative Director of Y/Project in 2013, the Paris-based label has combined conceptual and inventive detailing like the pinching feature. This slightly oversized long-sleeve button-down showcases the label’s pinched design by way of an embroidered logo implemented at the upper left torso. A clean yet sophisticated look.
Our Legacy - Popover Shirt
Swedish brand Our Legacy does not play when it comes to making garments truly oversized. Their Popover Shirt is definitely much more relaxed than your traditional button-down. Details like mother-of-pearl buttons, high side vents, and a dropped tail, as a single pocket is incorporated at the left chest, make this one of the best oversized shirts on this list, and an absolute gem in your fall wardrobe. No frills, no extra gimmicks or stitching, just a quality oversized shirt you can wear in any setting.
WACKO MARIA - Ghost In The Shell 2
For its latest pop culture-inspired delivery, WACKO MARIA is back with a capsule in homage to Ghost in the Shell 2: Innocence. The best piece? An oversized Hawaiian-style shirt.
Neighborhood - Solid Hawaiian Shirt
For the Japanese fashion aficionados looking at this list of the best-oversized shirts for fall, we have an open-collar shirt in cotton rayon with an embroidered Neighborhood logo on the left chest. Made of wood and pulp-based traceable material created with environmental considerations in mind, such as reducing carbon dioxide emissions and water pollution by up to 50%, you will not only sport an iconic Japanese streetwear brand, but you will be owning a timeless piece from their collection that is perfect for that weird transitional weather during fall.
Homme Plissè Issey Miyake
Another Japanese entry that doesn't need an introduction. Open spread collar, dropped shoulders, 100% polyester made in Japan. A classic and iconic oversized shirt to truly elevate your look this fall.
Comme Des Garcons Homme - Striped Shirt
Oversized shirts are essential for those days when the weather is a bit uncertain but also work really well when paired with a nice tee underneath. CMG Home offering, seen here embroidered with its boke flower logo is truly versatile for any formal or idle situation. Guaranteeing you’ll keep it in your wardrobe for as long as you like, this is one of those items that just stay 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.
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