Oversized tee + layering: a match made in heaven

There’s something about the oversized tee that just works. It’s comfy, cool, and easy to throw on no matter what your plans are. But if you want to take your oversized tee from “just chillin’” to “I actually made an effort,” layering is the trick. Seriously – add a denim jacket, cardigan, or even a turtleneck underneath and suddenly it looks like you know exactly what you’re doing.

At Oh So Pretty, we’ve got a wide range of oversized tees and all the bits and pieces you need to style them right. So if you're wondering how to make the most of this wardrobe essential, keep reading. We’re breaking down why the oversized tee and layering are a match made in heaven.

Why oversized tees are so good for layering

Oversized tees are already roomy and relaxed, which makes them perfect for slipping over or under other pieces. Unlike fitted shirts, they don’t cling or bunch up when you layer. And because they usually sit a bit longer, they add that extra bit of length and balance that makes layered looks feel effortless. You get warmth, comfort, and style – all in one easy combo.

Plus, an oversized tee can work in every season. Just change up the layers depending on the weather, and you’ve got endless outfit ideas.

Throw a jacket over it

This is one of the easiest ways to style your oversized tee. Grab your favourite jacket – denim, leather, bomber, or even a shacket – and chuck it on over your tee. You don’t need to think too hard about it.

Pair your oversized tee and jacket with leggings, bike shorts, or jeans, and you’ve got a laid-back look that’s still cool. Bonus points if you add some chunky sneakers or boots. Don’t forget to roll the sleeves of your jacket just a bit to show off the tee underneath.

At Oh So Pretty, we love pairing a crisp white oversized tee with a structured black blazer or cropped denim jacket. It’s the kind of look that works for brunch or a casual meeting and doesn’t try too hard.

Long sleeves underneath? Yes please.

This one gives total 90s vibes – and we’re here for it. Layering a long sleeve top under your oversized tee adds warmth and style in one go. Go for a striped or printed long sleeve to give your outfit some personality, or stick with black or white if you want to keep it simple.

You can even layer a fitted turtleneck under your oversized tee for a more put-together winter look. It keeps your neck warm and looks super stylish. Add a beanie and boots, and you’ve got a cool-weather outfit that looks like you planned it all out.

This layered look works well with both mini skirts and pants. Try an oversized tee with a black turtleneck, leather-look leggings, and combat boots. It's comfy, warm, and has that little bit of edge.

Vest and oversized tees are besties

If you want something soft and cosy, try layering a vest over your oversized tee. It gives off that “I just threw this on but still look good” vibe. Pair it with jeans and loafers or even slippers if you’re just staying in.

Vest are also great for adding colour or texture to your outfit. You could keep it neutral or go for something bold – either way, the oversized tee is the perfect base to build from.

A go-to look we love? A grey oversized tee with a colourful knit vest, black jeans, and white sneakers. Super simple, but still cute.

Go big with outerwear

Don’t be afraid to go oversized on top of oversized. Big coats, trench coats, and puffers all look great over a loose tee. Because oversized tees are light and comfy, you won’t feel too bulky even with a big coat on top.

Try this in winter: oversized tee, thermal long sleeve underneath, puffer jacket on top, joggers on the bottom, and boots to finish it off. You'll be warm but still stylish. The layering makes it look like you’ve put some thought into your outfit – even if you haven’t.

At Oh So Pretty, we stock pieces that work well with layering, like oversized tees in all kinds of colours, as well as outerwear that ties the whole look together.

Dress it up (yes, really)

Oversized tees aren’t just for lazy days. You can actually dress them up with the right layers. A fitted blazer, some nice jeans or tailored pants, and a good pair of boots or heels – suddenly your tee looks like part of a proper outfit.

Tuck the oversized tee slightly at the front or add a belt over it to give it a bit of shape. Pop on some gold jewellery, a cute bag, and you’re ready for dinner or drinks.

This trick works really well with plain oversized tees in black, white, or beige. They act like a blank canvas so your layers and accessories can do the talking.

Don’t forget accessories

A layered look with an oversized tee isn’t just about clothing. Accessories make a big difference. Think beanies, caps, chunky necklaces, hoop earrings, crossbody bags, and sunglasses.

Add a printed scarf over your tee and jacket combo or a statement necklace over your tee and turtleneck. Small touches like this bring the whole look together and show off your style.

Mix it up with textures

One way to make your oversized tee outfit more interesting is by mixing fabrics. Cotton tees with leather, denim, wool, or knits always look good together. Try a soft tee with a leather-look skirt and long cardigan. Or a basic black oversized tee with a silky midi skirt and cropped jacket.

You can also play with prints and colours. A plain tee layered with a printed long sleeve or a patterned cardigan adds a bit of fun.

Find your perfect oversized tee at Oh So Pretty

Looking for oversized tees that are easy to style and perfect for layering? Check out our online range at Oh So Pretty. We’ve got soft fabrics, relaxed fits, and all the colours you could want.

Whether you’re into basic whites or bold graphics, we’ve got something that’ll suit your style. And don’t forget – we’ve also got the cardigans, jackets, and accessories to pull the whole look together.

In short – the oversized tee is one of the best things you can have in your wardrobe. It’s comfy, stylish, and super easy to layer. With the right extras, you can wear it anywhere – from school drop-off to brunch, from work to the weekend. Grab a few from Oh So Pretty and get layering.