How to Style Oversized Tees and Shirts

Chrissie Milan
by Chrissie Milan

I wear oversized t-shirts and shirts with basically everything. They add layers to really simple looks which give your outfits a little bit more of an edge. I have three pieces, and I’ve styled each of them in two different ways, so I’m going to be showing you six looks.

Styling an oversized shirt

Outfit 1

Here I’ve styled an oversized white shirt with a v-neck crop top and some blue denim shorts along with the trainers and long socks, which is one of my favorite looks right now. This outfit is giving me holiday, summery vibes. Adding a shirt to a simple outfit like this just gives it a bit more character and makes you look a bit more put together.

How to style an oversized shirt

Outfit 2

I decided to style the shirt with a gray dress for the second outfit, and I added my pink converses for a pop of color. Truth be told, I’m not actually the biggest fan of bodycon dresses, but it makes it look a bit more put together with the shirt worn over it. 

Having a white shirt like this is such a great addition to your wardrobe - you can literally throw it on, and it just gives a look so much more oomph. There are also so many other ways to wear it: you can tie it up, wear it with jeans, wear it by itself with some heels - it’s just a very versatile top.

Easy oversized shirt style

Outfit 3

For look 3, I decided to go with an oversized black top. Graphic tees are a really big thing that are in right now; however, having just a plain black one is sometimes so much handier because it has so much more life in it. When you have a graphic tee, you can wear it so many times, and everyone knows that you’re wearing the same t-shirt. But just a plain black shirt, I could wear it a million times, and no one would say anything because it’s just a plain shirt.

Here I’m wearing it with some neon green cycling shorts, black heels, and a trapezoid-shaped bag. I think that the gold in the bag and the green of the cycling shorts go together really well. This is a cute and simple look that would be great for going out in the evenings.

Oversized shirt style

Outfit 4

I styled the black top again with some ripped blue jeans and some white trainers. I think it's just such a classic look to wear. It's just an outfit that you can pull on at any point, and when you wear it, you look stylish, but you probably 100% didn't even try. A black top with jeans is a completely effortless look.

Basic oversized shirt style

Outfit 5

Here I have my oversized pink tee. In this look, I've styled it with some white cycling shorts. I think that the pink and the white really go. Pastel colors like this pink are really in at the moment. I've also got on my white trainers and long socks and a Guess logo vintage bag. This is just a really cute and fun look with girly vibes.

White oversized shirt style

Outfit 6

This look is a bit more out there for me because I most likely would not wear this in public; it's just a bit too pink. But I don't know; maybe I would. I think that it looks kind of good? Here I decided to pair the same shirt with the matching pink sweatpants. I really like the pinks together. An oversized shirt with sweatpants is a really nice trend that is in right now that you can style up and look trendy. I decided to put these together with my white crocs. You're probably going to stand out quite a lot - everyone's going to see that you're wearing crocs and a matching pink sweatsuit, but that's ok, that's fine, stand out - don't dim your light for anyone else.

So there’s the lookbook for you. We’ve had a dress in there, we’ve had jeans, we’ve had shorts, we’ve had sweatpants, we’ve had cycling shorts - what more could you need? Oversized shirts and t-shirts are staples for you to have in your wardrobe. There are so many ways that you can wear them, so see what outfits you can create. They say go big or go home, I say go oversized or go home!

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