Fit. Is. Everything. Or so the menswear traditionalists like to espouse. But if form-hugging silhouettes truly are that important, then how do you explain fashion’s ongoing obsession with oversized T-shirts?
These things are everywhere, and that’s no exaggeration. Oversized T-shirts have been trending for so long that you may have become blind to them. From the thigh-tickling longline tees popularised by Kanye West and Jerry Lorenzo in the mid 2010s to the cropped, slouchy ones favoured by Gen Z fashion TikTokkers. It could be argued that it’s beyond a trend now. Slouchy, boxy, baggy – it’s near enough the default setting for tees here in the 2020s, and that’s no bad thing.
Oversized T-shirts are airier, more comfortable and excellent for layering. Sure, there’s still a time and a place for a slim-fitting, Steve McQueen-esque plain white tee – there always will be – but the best oversized t-shirts deserve their own spot in the pantheon of menswear staples. And if you don’t own one already, here’s what you need to know…
How should an oversized T-shirt fit?
Don’t get it twisted, ‘oversized’ is not a synonym for ‘too big’. There’s a difference, and it’s important to understand it if you want to get this piece right.
Men’s oversized T-shirts should be loose without appearing unintentionally sloppy. The shoulder seams should sit slightly lower than your natural shoulder line (those in the business call this a ‘dropped shoulder’), and the sleeves should extend a few inches past the bicep without going past the elbow.
Length is more of a grey area. Some oversized tees are designed to fall just above mid-thigh, while others are deliberately cropped for more of a boxy look. If you go for the former, it’s important that the T-shirt doesn’t completely swallow your frame. Look for designs that offer a boxy shape without excessive fabric, keeping the proportions balanced and intentional.
How to style an oversized T-shirt
Styling an oversized T-shirt is all about balance. The key is to pair it with more fitted pieces to create contrast, avoiding an overly baggy look. For a casual outfit, wear it with slim-fit jeans or tailored chinos. This helps maintain structure in the overall outfit while allowing the oversized shirt to be the focal point. If you’re going for a more relaxed, streetwear-inspired look, consider pairing the tee with sweatpants or relaxed-fit jeans.
Layering is another effective way to style an oversized T-shirt. Throwing on a jacket or an open flannel shirt can add depth to the outfit while also refining the silhouette. But that’s just the beginning. You could throw on some knitwear, an overshirt, a gilet… hell, why not even top it off with some more substantial outerwear. Even underneath all of this, the best oversized T-shirts will still be visible, poking out at the bottom to give your outfit depth.
Footwear matters, too. Chunky sneakers or high-top trainers complement the oversized aesthetic, especially in streetwear contexts. For a more refined approach, clean white sneakers or loafers work well when paired with smarter trousers or chinos.
By keeping the rest of your outfit fitted and considering layers, you can ensure your oversized T-shirt looks intentional and stylish, rather than just loose and unstructured.
The best oversized T-shirt brands
Artknit Studios
Artknit Studios is a brand quietly excelling with a focus on sustainability and craftsmanship. Based in Italy, it offers timeless essentials built to last. Their oversized T-shirts are a perfect example of this ethos.
These tees are made from organic cotton with a soft, broken-in feel. The neutral colour palette of whites, greys, and blues makes them versatile enough to wear solo or under a blazer for a refined casual look. With a relaxed yet structured fit, they avoid the sloppy connotations of oversized styles. And while not cheap at £70 to £100, they are a solid investment you'll wear repeatedly.
Uniqlo U
Designed by Christophe Lemaire, Uniqlo U presents high-quality basics at affordable prices. Known for its relaxed, structured fit, the oversized T-shirts from this line offer a premium feel without a premium price tag.
These tees are crafted from heavyweight cotton and come in a wide range of neutral and seasonal colours, making them versatile for both casual and smart outfits. Their attention to detail, like boxy proportions and dropped shoulders, ensures a modern oversized look that’s accessible to everyone. You’ll typically find these tees for under £20, proving that high-end design doesn’t have to break the bank.
CLOSED
CLOSED, a German brand founded in 1978, has built its reputation on European craftsmanship and understated style. Their oversized T-shirts reflect this blend of simplicity and sophistication.
Made from premium cotton, these tees feature a structured fit that feels polished rather than sloppy. The muted colour options like navy, off-white, and grey are versatile enough for any occasion, from casual outings to smarter settings with tailored trousers. Reinforced stitching and dropped shoulders add a refined touch. Priced between £90 and £120, these tees offer a lasting investment in effortless, everyday style.
COS
COS is synonymous with minimalist elegance, and their oversized T-shirts carry that signature refinement. Known for clean lines and quality fabrics, COS focuses on creating wardrobe staples that transcend trends.
Their oversized T-shirts are crafted from soft organic cotton and feature boxy cuts that offer a structured, polished look. Available in muted colours, these tees work well for layering or as a statement piece in casual outfits. Prices range from £25 to £50, offering a blend of high-quality construction with timeless appeal.
PANGAIA
PANGAIA redefines sustainable fashion with innovative, eco-friendly practices, and their oversized T-shirts are no exception. This brand fuses cutting-edge materials with bold design.
The oversized tees come in a wide range of vivid colours, from bright pinks to earthy tones, offering a pop of personality in your wardrobe. Made from organic cotton and sometimes blended with recycled fibres, these tees are designed to be both planet-friendly and supremely comfortable. Priced around £70 to £90, PANGAIA’s T-shirts are an excellent investment for anyone committed to sustainability without sacrificing style.
Acne Studios
Swedish brand Acne Studios is celebrated for its avant-garde approach, and their oversized T-shirts perfectly blend streetwear and high-fashion influences.
These tees feature dropped shoulders and boxy cuts that give them a bold yet wearable silhouette. Acne’s use of high-quality fabrics ensures comfort while maintaining structure. With prices ranging from £120 to £200, these tees make a statement, offering a designer edge for those looking to elevate their casual wardrobe.
CDLP
Swedish brand CDLP offers minimalist luxury in every piece, and their oversized T-shirts are no exception. Known for its focus on sustainability, CDLP crafts these tees from a blend of organic Pima cotton and Lyocell, making them ultra-soft and breathable.
With a generous fit that remains polished, these tees come in classic shades like black, white, and navy. They are versatile for both lounging and layering, priced between £70 and £95. CDLP is perfect for those seeking a blend of simplicity and sophistication in their everyday essentials.
Noah NYC
Noah NYC, the brainchild of former Supreme creative director Brendon Babenzien, merges streetwear, surf, and skate culture with a commitment to sustainability.
Their oversized T-shirts feature bold graphics and minimalist branding, adding a laid-back, casual vibe. The relaxed fit is comfortable yet intentional, offering high-quality construction at a price point that typically falls around £50 to £90. Noah NYC’s tees reflect a blend of streetwear influence and ethical production, making them both fashionable and responsible.
Carhartt WIP
Carhartt Work In Progress (WIP) is the fashion-forward arm of the iconic American workwear brand Carhartt, known for rugged, durable clothing with an urban twist.
Their oversized T-shirts are crafted from heavyweight cotton, designed to last while maintaining a relaxed fit. With subtle logos and a focus on quality, these tees blend workwear durability with modern street style. Priced from £40 to £70, Carhartt WIP is ideal for those who want reliable, long-lasting pieces that work across casual and streetwear wardrobes.
Stüssy
A pioneer in streetwear, Stüssy has been making waves since the 1980s with its surf and skate-inspired aesthetic. Their oversized T-shirts are an emblem of laid-back California cool.
These tees often feature bold graphics and the iconic Stüssy logo, offering a loose, comfortable fit perfect for casual wear. They pair well with a variety of outfits, from denim to sweatpants. Typically priced between £40 and £60, Stüssy’s tees are a must-have for anyone looking to tap into the streetwear culture.
Wax London
Wax London combines classic British casualwear with modern sustainability, and their oversized T-shirts reflect this blend of tradition and innovation.
Crafted from soft organic cotton, these tees offer a boxy silhouette that provides a relaxed yet considered look. Available in muted tones and playful stripes, they bring a subtle character to any outfit. Priced between £50 and £70, Wax London offers an accessible way to incorporate British craftsmanship into your wardrobe.
Oversized T-shirt FAQs
What is an oversized T-shirt?
An oversized T-shirt is a loose-fitting top with a relaxed silhouette, offering more room in the body and sleeves compared to standard tees.
Should I size up for an oversized T-shirt?
Not necessarily. Most oversized T-shirts are designed with extra room, so your regular size should give the desired fit.
Are oversized T-shirts flattering?
Yes, they can be! The looser fit works well on most body types and creates a laid-back, effortless style.
Can I wear an oversized T-shirt to work?
For a smart-casual setting, an oversized tee paired with tailored trousers and a blazer can work, but avoid it in more formal environments.
What fabric is best for oversized T-shirts?
Soft, breathable fabrics like organic cotton or cotton blends are ideal for comfort and durability.
Are oversized T-shirts in fashion?
Yes, oversized T-shirts remain a key trend in casual menswear, offering both comfort and style.
How do I care for oversized T-shirts?
Always check the label, but most can be machine washed on a gentle cycle to maintain their shape and softness.
What's the difference between oversized and baggy T-shirts?
Oversized T-shirts are designed with a relaxed fit but still maintain a shape, while baggy tees are often shapeless and extra loose-fitting.
Up next, organic cotton T-shirts every modern man should own.
