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As the 90s come back in style, or even Y2K style for that matter, we will see some oversized and baggy clothing coming back. We looked at hundreds of AI generated images for how to wear oversized shirts men.

What did we find? The best ways for how to wear oversized shirts for men is to wear cuffed and cropped pants, low-cut shoes, and sometimes it’s cool to do the top buttons fully.

1. Ankle Pants with rolled-up cuffs


This is an interesting way to wear an oversized button-up collared shirt. Leave it unbuttoned and wear some pleated rolled-up ankle pants that are also slightly loose. I really think the thing that makes an aesthetic difference here is the rolling of the sleeves and how the dress shirt seems to go up and cut on the sides.

2. Rolled-Up Pants Showing Ankle


From what I’ve looked at, there seems to a general consensus that you can wear an oversized shirt with slightly looser pants as long as the cuffs are rolled up and you show some ankle. Haha I like it.

3. Wear With Shorts


This is kind of cool to me because you can see how it correlates with the rolled up look and the 3/4 style pants showing ankle. I probably wouldn’t wear this but fashion is fashion and this could actually work.

4. Make it patterned or checkered


Some of the coolest options that I’ve seen are oversized shirts that have a pattern to them. Usually the checkered or plaid style works really well.

See also  Black Polo With What Color Pants?

5. Tight Ripped Jeans


I think this just makes the look more like it was planned as opposed to your clothes don’t fit. Also the color choice here is important as they completely oppose each other. Also notice the sleeves are rolled or short on this one so that plays a factor as well.

6. Fully Button To The Top Button


I see many of the options doing the top button up fully with the oversize shirt look with tight jeans.

7. Use Bold Colors


Using a single bold color as your oversized shirt is a really cool way to add a little bit of flair to the fashion. Honestly, using the more dull colors with the oversized shirt look kind of just looks like someone trying to wear a shirt but it doesn’t fit them. There is a fine line between them, and you want to be on the right side of it.

Hey, my name is Matt Edward. My life changed when I started dressing better and taking care of my appearance. I wanted to share that enthusiasm and passion with you through these carefully curated and designed blog posts about men's fashion and lifestyle improvements. Cheers.

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