How to Properly Style an Oversized Shirt

Oversized shirts are taking over the fashion world by storm. From runways to Instagram feeds, chances are you’ve seen your favorite celebs and influencers rocking this effortlessly chic look. But let’s be honest, there’s a fine line between fashionably oversized and looking like you accidentally grabbed something from your dad’s vintage collection. That’s where things get tricky.
If you’ve been eyeing this trend but aren’t sure how to properly style an oversized shirt without feeling swallowed alive, this guide is your ultimate cheat sheet. You’ll strut away with all the know-how to nail that perfect balance between comfort and fashion-forward style.
Whether you’re heading to brunch, running errands, or even dressing up for date night, oversized shirts can do it all. Here’s how to make the trend work for you!
Why Oversized Shirts Are a Trend
There’s something irresistibly cool about oversized shirts. They exude effortless style while being comfy enough to wear all day long.
This trend is all about merging comfort with versatility. You can wear an oversized shirt with heels and bold accessories or dress down with sneakers and a messy bun. Plus, they flatter different body types, making them a go-to piece for anyone who wants to look polished yet relaxed.
And let’s be honest, anything that lets you slay in style and breathe easily after that second brunch mimosa is already a win, right?
Tips for Choosing the Right Oversized Shirt
The key to nailing this trend starts with finding the perfect oversized shirt. It’s more than just choosing a bigger size. Here’s your shopping game plan when shopping at your favorite online clothing boutique or in-store.
You’ll want to size up, but not too much. You want the shirt to be oversized but still flattering. Aim for one or two sizes bigger than your regular fit. Anything larger might have you swimming in fabric rather than sporting a stylish look.
Fabric is your friend. Look for structured fabrics like cotton or linen if you want a polished look. For something more flowy and casual, go for a lightweight material.
Focus on the length. The longer the shirt, the more versatile it’ll be for tucking, knotting, and layering. Ideally, it should at least cover your hips and possibly more.
The goal here is oversized, not drowning. Keep it oversized with the intent to nail the chic factor.

Avoid Baggy Bottoms
When styling an oversized shirt, balance is everything. Pairing an oversized shirt with equally loose or baggy bottoms can quickly take your outfit into frumpy town. Don’t get us wrong, that look is comfortable, but it might not exactly scream stylish.
Instead, choose bottoms that keep things proportional. Skinny jeans, leggings, or fitted shorts work wonders to balance out the volume on top. If you’re feeling adventurous, you can try biker shorts for that sporty-chic vibe.
The secret? Keep the focus on the shirt while creating a sleek silhouette on the bottom.
The Art of Tucking the Shirt In
Tucking in an oversized shirt is your secret weapon to transform your look. Whether a full tuck, a half tuck, or a French tuck, this technique makes your outfit look polished and intentional.
- Full Tuck: Great for high-waisted jeans, pants, or skirts. It creates a defined waistline and makes your legs look longer.
- Half Tuck: Keep it casual and cool by tucking in the front half of your shirt while leaving the back loose. Perfect for that effortlessly stylish vibe.
- French Tuck: Just tuck in a small section at the front center of your shirt. This works particularly well with jeans and gives your outfit a relaxed feel.
Consider Layering the Oversized Shirt
If you’re looking to play around with textures and add depth to your outfit, layering is your best friend. Oversized shirts are perfect for that effortlessly layered look.
Layer your oversized shirt like a fashion pro by wearing it over a tank top or crop top for a casual, relaxed vibe. For a more polished edge, try wearing it under a structured blazer, balancing professional and edgy in one outfit. Alternatively, leaving the shirt open and unbuttoned over a fitted dress or top creates a light and breezy aesthetic.
Think of your oversized shirt as the fashion gift that keeps on giving; it’s one piece that can be styled in dozens of ways to give you countless outfit options.
Give a Cropped Effect With Knots
Knots are a game-changer when it comes to styling oversized shirts. They take something loose and flowy and give it a tailored, cropped effect with minimal effort.
Here’s how to master the knot game.
- Unbutton the bottom half of your oversized shirt.
- Tie the ends together snugly at your waist or just above your belly button.
- If it’s an oversized graphic tee, you can twist the hem to give you a place to tie the knot.
- Adjust the rest of the shirt for a flattering fit.

Use a Belt To Create a Silhouette
Oversized shirts are great, but sometimes they need a little structure. A chic belt is your go-to for this. Cinching your shirt at the waist with a statement belt can completely change the vibe of your outfit.
This works particularly well with button-up oversized shirts that can double as shirt dresses. Add knee-high boots to the mix, and you’ve got an outfit that’s both chic and comfy.
Pro tip: Experiment with wide belts for bold, defining looks, or stick to slim belts for subtler silhouettes.
Quick Styling Ideas for Different Occasions
Need some inspiration? We’ve got you covered! You might have an outfit idea in your head, but here is how you can pair it with the right occasion or event.
- Brunch with friends: Pair a flowy oversized shirt with skinny jeans and ankle boots. Throw on a cute crossbody bag, and you’re ready to sip mimosas in style.
- Date night: Knot your shirt at the waist and pair it with a leather skirt and strappy heels for an effortlessly glam look.
- Running errands: Keep it casual by layering your oversized shirt with high-waisted biker shorts. Add sneakers to complete the look.
- Office chic: Tuck your shirt into tailored trousers, layer it under a blazer, and finish with loafers or pumps.
You’re now a pro in properly styling an oversized shirt! Now, it’s time to put these tips into practice. Whether you’re playing with knots, layering, or cinching your shirt with a belt, there are endless ways to make this trend work for you.
Still searching for that perfect oversized shirt? Check out Arrow 22’s trendy online boutique for pieces that’ll make your fashion-loving heart skip a beat. Whatever you choose, owning an oversized shirt is a serious fashion win!
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