Style Oversized Shirts Four Ways


Oversized shirts have a lot of potential when it comes to fashion, but they are also really easy to screw up. This tutorial will go through a number of different looks and teach you how to style oversized t-shirts. Stick around for some awesome inspiration.


Style oversized shirts

Casual with a pop of dressy 

For the first look, we are starting with a simple gray cropped top and some matching joggers. Next, I am adding an oversized checkered shirt. I went for one with a hood that matches my sweatsuit and is about three sizes too big. The bigger size will give it length as well as that baggy look. I went a little bold with my shoes and matched the maroon from my top to some cool heeled boots. I think the boots just added that extra detail and personality I was looking for! 

Oversized shirt style

Baggy and sporty

For the second outfit, we are starting with an all-white base. I am wearing a dress length white oversized t-shirt with some matching white socks and sneakers. Next, I threw a blue checkered shirt over the white t-shirt for a baggy and sporty look. 

How to style oversized t-shirt

Rock a little red 

This time, the base we are starting with is full black. I went with some biker shorts and a crop top, but you can totally wear a full-length shirt if you’re not comfortable with showing so much skin. I added a red checkered shirt (one that’s the same length as my shorts) and pulled the sleeves up. To finish the outfit, I added a chunky boot. Chunky boots are super in right now and really great for adding a little personality to an outfit. 

Women’s oversized shirt style

Button up dress style 

Finally, we’ve come to our last look! We are starting off with a nice pair of overalls with a small cropped white shirt underneath. Next, we are adding a button-up shirt dress in the same color as the overalls. Cuff up the sleeves and keep the dress hanging open. Add a pair of white sneakers and you’re ready to go! 


There you have it, four fun ways to style oversized shirts. I think a little baggy detail looks great - especially with some tighter bases. I’d love to see the ways you guys style your oversized shirts as well - let me see down below! 

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