Oversized shirts are a wardrobe staple, blending comfort with versatility. But there’s a fine line between relaxed chic and downright sloppy.
The secret to nailing the look is all about balance—pairing proportions, adding the right accessories, and playing with textures. Whether you’re heading to brunch, the office, or just lounging around, oversized shirts can work for every occasion.
These 17 styling tips will help you elevate your look while staying comfortable and effortlessly fashionable.
Tuck It Into High-Waisted Jeans
The ultimate casual-chic vibe. Tucking an oversized shirt into high-waisted jeans creates a flattering silhouette.
The loose top contrasts with the fitted bottom, defining your waist and elongating your legs. Add a belt for extra flair, and complete the look with sneakers or ankle boots for a stylish, everyday outfit.
Cinch It with a Belt
Define your waist in seconds. Transform an oversized shirt into a structured outfit by cinching it with a belt.
Choose a wide or statement belt to add drama, or go with a slim one for a subtle touch. This trick works well with oversized button-ups or tunics, instantly creating an hourglass shape.
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Pair It with Biker Shorts
Athleisure done right. For a trendy, casual look, pair an oversized shirt with biker shorts.
The fitted shorts balance the volume of the shirt, creating a modern silhouette. Add chunky sneakers and a crossbody bag for a sporty outfit perfect for errands or coffee runs.
Knot It at the Waist
Turn oversized into cropped. Tie a knot at the front of your oversized shirt for an instant cropped look. This style works perfectly with high-waisted skirts or pants.
It adds shape to your outfit while keeping things playful and relaxed.
Layer Over a Turtleneck
Sophisticated and cozy. For cooler days, layer your oversized shirt over a fitted turtleneck.
The combination of textures adds depth to your outfit while keeping you warm. Stick to neutral tones for a sleek look, or experiment with contrasting colors for a bolder vibe.
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Wear It as a Dress
Minimal effort, maximum style. If the length allows, oversized shirts can double as dresses. Pair yours with knee-high boots or tights for a chic and effortless ensemble.
Add a belt or blazer to elevate the look for more formal settings.
Roll Up the Sleeves
Simple tweaks, big difference. Rolling up the sleeves of an oversized shirt can make all the difference.
It adds structure to the look and creates a more polished vibe. Pair this with slim-fit pants or leggings for a balanced outfit.
Add a Blazer
Mix structured with loose. Throwing a tailored blazer over an oversized shirt creates an interesting juxtaposition.
The sharp lines of the blazer balance the relaxed fit of the shirt, making it a great option for work or smart-casual outings.
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Pair with Wide-Leg Pants
Go bold with proportions. Contrary to popular belief, oversized on oversized can work beautifully when done right.
Pair your shirt with wide-leg trousers, but make sure the colors and fabrics complement each other. Add a sleek accessory like a clutch to tie the look together.
Layer Under a Sweater Vest
Trendy and preppy. Layering an oversized shirt under a sweater vest is both fashionable and functional.
The combination creates a preppy vibe that’s perfect for fall. Let the shirt’s hem and cuffs peek out for added detail.
Add a Corset
From boxy to bold. A corset over an oversized shirt is a striking way to create contrast. It accentuates your curves while keeping the shirt’s relaxed vibe intact.
This is a great option for nights out or when you want to make a statement.
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Half-Tuck the Front
Effortless and stylish. Tuck just the front portion of your oversized shirt into your pants or skirt. This technique creates a relaxed yet intentional look.
Pair with loafers or heels for a polished finish.
Pair with Skinny Jeans
Keep it sleek on the bottom. Balancing an oversized top with skinny jeans is a classic move.
The contrast between the loose shirt and fitted pants creates a streamlined look. Add ankle boots or sneakers to complete the outfit.
Wear with Over-the-Knee Boots
Edgy and glamorous. Turn your oversized shirt into a bold statement piece by pairing it with over-the-knee boots.
This combination elongates your legs and gives off an effortlessly edgy vibe. Perfect for a night out or a stylish brunch.
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Add a Statement Necklace
Dress it up instantly. Oversized shirts can sometimes look too casual, but adding a bold necklace can change that.
Choose a chunky chain or colorful beads to draw attention to your neckline. This simple addition instantly elevates your look.
Layer Under a Sleeveless Dress
A fresh way to mix styles. An oversized shirt layered under a sleeveless dress creates an unconventional yet stylish outfit.
The shirt adds depth and makes the dress suitable for more casual settings. Choose a dress with a fitted silhouette for the perfect contrast.
Go Monochrome
Simplify with one color. Choose a single color palette for your entire outfit, pairing your oversized shirt with pants or skirts in the same shade.
This creates a cohesive, elegant look that’s effortlessly chic. Add a pop of color with your shoes or accessories for a standout finish.
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