Let’s be honest: the oversized shirt is like that dependable friend who’s always there when you need them—effortlessly cool, endlessly versatile, and universally flattering. But let’s face it, styling a shirt that’s three sizes too big (by design) can sometimes leave you feeling like you’re drowning in fabric rather than swimming in style. Fret not! We’ve cracked the code on how to make this wardrobe essential work for every occasion. Whether you’re aiming for polished, playful, or off-duty vibes, these tips will have you rocking your oversized shirt with confidence.
Ways to Style an Oversized Shirt
1. With High-Waisted Jeans and a Belt
Why it works: High-waisted jeans balance the loose fit of the shirt, while a belt cinches your waist to give structure to the look.
Pro Tip: Opt for a statement belt to add a pop of personality—think chunky buckles, bold colours, or textured leather. For an added twist, roll up the sleeves for a relaxed vibe.
2. With a Sweater and Miniskirt
Why it works: A fitted sweater layered over the oversized shirt adds shape, while a miniskirt creates a playful, youthful silhouette.
Pro Tip: Let the shirt’s hem and collar peek out for added texture. Finish the look with knee-high boots or chunky loafers to nail the preppy aesthetic.
3. With Biker Shorts and Sneakers
Why it works: The slim silhouette of biker shorts contrasts perfectly with the oversized shirt, creating a sporty yet chic outfit.
Pro Tip: Go for a slightly unbuttoned look and pair it with bold sneakers and a crossbody bag. For extra flair, layer a crop top underneath the shirt.
4. As a Dress with a Belt
Why it works: Wearing an oversized shirt as a dress keeps things simple and effortlessly stylish, while a belt adds definition to your waist.
Pro Tip: Choose a shirt that’s long enough to work as a dress and pair it with heeled boots or strappy sandals. Add tights or leggings for colder weather.
5. Open Over a Tank Top and Shorts
Why it works: This relaxed, open-shirt look exudes casual coolness, perfect for summer days or beach vacations.
Pro Tip: Stick to contrasting colors—like a white tank with black shorts or vice versa—for a sleek, minimalist look. Accessorize with layered necklaces.
6. Tucked into Wide-Leg Pants
Why it works: Wide-leg trousers create a flowy silhouette that pairs beautifully with a tucked-in oversized shirt for a high-fashion look.
Pro Tip: Opt for a monochrome palette to keep it elegant and cohesive. Add heels or platform shoes to elongate your frame.
7. Knotted at the Waist with a Maxi Skirt
Why it works: Tying the shirt at the waist adds a playful touch to the oversized silhouette, while a maxi skirt brings bohemian elegance.
Pro Tip: Choose a skirt with a bold print or texture to contrast with the simplicity of the shirt. Add a pair of gladiator sandals or espadrilles.
8. Under a Corset Top with Pants
Why it works: Layering an oversized shirt under a corset adds structure and drama.
Pro Tip: Go for a cropped corset to highlight your waist. Add bold earrings or a clutch for a night-out look.
9. With a Slip Dress and Heels
Why it works: A slip dress brings femininity, while the oversized shirt adds a casual, effortless layer.
Pro Tip: Leave the shirt unbuttoned for a laid-back vibe. Choose heels or mules for an elevated touch.
10. Half-Tucked with Straight-Leg Trousers
Why it works: The half-tuck creates an asymmetrical, effortlessly chic silhouette.
Pro Tip: Use a silk or satin oversized shirt for a touch of luxury. Add gold jewelry for a polished finish.
11. As a Beach Cover-Up with Sandals
Why it works: An oversized linen or cotton shirt doubles as a breezy, stylish cover-up.
Pro Tip: Roll up the sleeves and accessorize with a straw hat and tote bag for full vacation vibes.
12. Under an Oversized Blazer with Bike Shorts
Why it works: The structured blazer contrasts with the relaxed shirt, creating a modern, layered look.
Pro Tip: Stick to neutral tones for a sophisticated streetwear vibe. Complete the look with sleek sneakers or ankle boots.
13. With Skinny Jeans and Over-the-Knee Boots
Why it works: Skinny jeans and tall boots balance the oversized silhouette of the shirt, creating a streamlined look.
Pro Tip: Go for a shirt with a bold print to keep it interesting, and add a sleek crossbody bag.
14. With a Sweater Vest and Chunky Loafers
Why it works: Sweater vests add structure to the oversized shirt, while chunky loafers keep it grounded.
Pro Tip: Experiment with bright or pastel colors to make the outfit pop. Add crew socks for a retro vibe.
15. With Denim Shorts and Sneakers
Why it works: The contrast between the oversized shirt and fitted shorts creates a balanced, relaxed outfit.
Pro Tip: Tuck one side of the shirt into the shorts for a playful, undone look.
16. Layered Under a Crop Top with Cargo Pants
Why it works: The oversized shirt adds dimension to the crop top, while cargo pants keep the look functional and cool.
Pro Tip: Roll up the sleeves and add chunky sneakers or combat boots for extra edge.
17. Over a Midi Dress
Why it works: If you tie the shirt at the waist it creates shape, while the midi dress keeps things feminine.
Pro Tip: Choose a shirt in a contrasting fabric or color to add depth to the outfit.
18. With a Turtleneck and Plaid Skirt
Why it works: A turtleneck adds warmth, while a plaid skirt brings a preppy, seasonal touch.
Pro Tip: Layer with tights and ankle boots for a cozy fall outfit.
19. Open Over a Jumpsuit
Why it works: An oversized shirt acts as a stylish layering piece over a fitted jumpsuit.
Pro Tip: Choose a lightweight fabric for easy movement. Add hoop earrings and sneakers to complete the look.
20. As a Statement Piece with Monochrome Layers
Why it works: A bold oversized shirt stands out when paired with simple, monochrome pieces.
Pro Tip: Keep accessories minimal and let the shirt do the talking.
The oversized shirt isn’t just a wardrobe staple—it’s a styling powerhouse. From casual beach days to polished work outfits, this piece proves its versatility time and again. So the next time you reach for that oversized button-up, remember: the possibilities are as endless as your creativity. Style it your way, and let your outfit do all the talking!
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