Let’s face it: oversized t-shirts are very comfortable. Comfortable to the point that you can give off lazy vibes if you don’t get the look right! Sometimes the look doesn’t matter, for example, you’re just chilling at home and just need something that allows you to feel relaxed. However, if you’re wearing an oversized t-shirt out and about, getting some details right could make you look like a chill guy.
Before we discuss the tips, there is one thing that we have to clear up to avoid some confusion.
What is the difference between a boxy t-shirt and an oversized t-shirt?
Oversized clothing does not necessarily mean a boxy fit.
Most boxy fit items are not oversized.
This is mainly down to the fact that boxy fits are shorter than oversized items even if both are wide.
Boxy fits will therefore usually only be as long as regular items and end at or just below your waist. Oversized items will usually end close to the middle of your thighs (or perhaps lower!)
Here’s how to maximise the potential of your oversized t-shirt with practical, fashion-forward tips.
1. Classic casual
Combine your oversized tee with straight-fit jeans or chinos. Go for darker colours for an elevated casual look. Roll up the sleeves slightly to give structure and pair with classic white sneakers for a timeless finish.
This iteration is slightly different to the classic power combination or red, white and blue but still makes an impact with its bold colours.
2. The art of layering
Layering adds depth and versatility to your outfit. Wear an open flannel shirt, lightweight denim jacket, or casual bomber jacket over your oversized tee. Keep the layering pieces neutral or complementary to the tee's colour for a cohesive look. In the spring and autumn where perhaps you cannot come down to single-layer outfits, layered outfits will be your go-to and there is a place for oversized t-shirts in this fit even if they are not the most visible.
3. Urban streetwear style
Capture the urban streetwear vibe by pairing your oversized t-shirt with tapered joggers, cargo pants, or distressed jeans. Bold sneakers, a bucket hat, and a trendy cross-body bag will enhance this look. Consider graphic prints or bold colours to make a strong fashion statement.
Our model above opted to tuck in the t-shirt as way of managing his outfit proportions (see tip no. 7 below).
4. Smart-casual balance
Contrary to belief, oversized tees can also feature in smart-casual outfits. Tuck your tee into tailored trousers or chinos, and complement the look with loafers or minimalist sneakers. Adding a structured blazer or a stylish cardigan creates an effortlessly sophisticated appearance.
Our model opted for quiet luxury colours to add even more smartness into the mix.
5. Summer-ready styles
Oversized t-shirts excel in hot weather due to their breathability and comfort. Pair them with casual shorts, such as chinos or denim shorts, and finish the look with slides or canvas sneakers. Choose lighter colours and breathable fabrics like organic cotton for maximum comfort.
In summer, it can be tricky to get the right balance between catching attention with bright colours and staying cool with lighter colours. Footwear could be one way to get attention.
6. Elevated accessories
Accessories can transform your oversized tee outfit from basic to stylish instantly. Opt for a minimalist watch, layered necklaces, or sleek sunglasses to enhance your outfit. Accessories provide subtle detail without overwhelming the laid-back charm of an oversized tee.
The point here is not about extravagant choices but coherent ones. There are two watch styles on this page (compare the one above with outfit 3); if we had flipped these two watches in the respective images, they would look out of place, irrespective of whichever brand they are.
7. Proportions matter
But not in the way you might think. When styling oversized clothing, often the advice is to maintain balance. You’ll frequently hear things like pair loose tops with more fitted bottoms to maintain shape and avoid an overly baggy appearance. Similarly, advice may extend to suggesting a tapered or slim-fit bottom to ensure your style stays intentional and flattering.
Our thoughts on this are perhaps more nuanced than we have expressed before. A lot of this depends on the body shape of the person wearing these outfits. So it’s not as simple as saying that the outfit is either wrong or it works for everyone. Just that it may not work for a lot of people and if it doesn’t for you, that’s ok. Confidence in our clothes matters a lot!
Final thoughts
Oversized t-shirts are incredibly versatile wardrobe essentials. With thoughtful styling, they can provide you with outfit options for casual outings to more polished affairs. Experiment with proportions, layers, and accessories to find your perfect oversized tee style.
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