How to Wear an Oversized Shirt

Co-authored by Lauren Schugar

Last Updated: November 25, 2022 References

Oversized shirts are usually really comfortable and great for lounging around all day. Oversized shirts are great for relaxation, but they can also be worn in a fashionable way if styled correctly. You could buy a cheap T-shirt, or buy a very large button-up shirt. There are as many possibilities as you can imagine when it comes to styling an oversized shirt. You can keep it casual, dress it up, or, if the shirt is long enough, wear it as a dress.

Method 1

Method 1 of 3:

Keeping it Casual

1
Wear it with slim fit jeans and sneakers. This is a very simple and cute look that can be worn around the house, to run errands, or out to lunch with a friend. You can choose a plain white T-shirt, or a button-up shirt. Choose a pair of jeans that are fairly tight on you. You can wear any sneakers, but a pair of solid-colored sneakers would be especially cute.
- Wear a T-shirt with ripped skinny jeans and plain white sneakers.
- Put on a large button-up shirt and leave it untucked. Pair it with black jeans and dark sneakers.
2
Layer it over a long sleeved shirt. Go for an edgy look by wearing an oversized black shirt over a long sleeved, form-fitting black shirt. Tuck the shirts into a pair of high-rise pants. Wear it with black boots or sneakers.^{[1]
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- Wear a shirt with your heavy metal or rock band logo on it.
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3
Pair it with a long skirt. This is a super comfortable look that is pretty trendy lately. Put on an oversized T-shirt. Then, tuck it into a long pencil skirt. Pair the outfit with white sneakers and you will be stylish, yet comfy enough to curl up for a nap.^{[2]
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- Wear a black shirt with a white design on it, black pencil skirt, and plain white sneakers.
4
Go for sweatpants to be ultra comfortable. Luckily, wearing loungewear and sportswear are acceptable now to wear as a fashionable outfit if styled the right way. Look for an oversized T-shirt in a solid color. Wear a pair of sweatpants that match the color of the shirt. Then, put on a pair solid-colored sneakers or sneakers that match the color of the rest of your outfit.^{[3]
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- Wear a black shirt, black sweatpants, and white sneakers.
- Look for a pair of sweatpants that are fairly form-fitting.

Method 2

Method 2 of 3:

Dressing it Up

1
Wear it with a blazer. An oversized T-shirt isn’t just for an ultra casual look if you pair it with the right outfit. Look for a blazer that is fairly form-fitting but long. Put on an oversized button-up and leave a few of the bottom buttons undone. Pair this with a pair of dress pants and the shoes of your choice. Then, you have an office look for a relaxed work environment, or a stylish look for a night out.
- Wear a black blazer, a white button-up, black pants, and white sneakers.
2
Let it fall off of the shoulders. This is a great look for a night out. Look for a long-sleeved shirt that could easily be worn off the shoulders. Pair the shirt with a nice pair of pants and stilettos. You can choose to wear ballerina flats or sandals if heels aren’t your thing.
- Wear a long-sleeved button up with a few of the top buttons undone. Then, wear a pair of ankle-length dress pants and nude-colored stilettos.
3
Mix your patterns. This is a fun and quirky look that is great for either a day or night out. Look for an oversized T-shirt with the pattern of your choice. Stripes would be a good option. Then, put on a pair of pants with a loud print. For shoes, espadrilles, sandals, or plain sneakers would work well.^{[4]
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- You can completely clash with the patterns by choosing different prints and colors, or wear different patterns but similar colors.
- Wear a T-shirt with thin stripes, pants with a large geometric pattern, and plain sandals.
4
Leave it unbuttoned. Transform your office look for a night out. Wear a button-up T-shirt and leave a few of the top buttons undone. Pair the shirt with a belt and high-rise skinny jeans. You can wear stilettos, loafers, or ballerina flats.
- Wear a silk button-up, lace bralette, and black skinny jeans.
5
Put on a skirt and heels. This is a look that says laid back but also very sexy. You can wear just about any shirt for this look, but a button-up is an easy way to dress the outfit up. Pair the shirt with a black mini skirt and pair of heels or ankle boots.
- Wear a white button-up and tuck in only one side of it. Pair it with leather mini skirt and black ankle boots.

Method 3

Method 3 of 3:

Wearing it as a Dress

1
Turn it into a shirt dress. Wearing your oversized T-shirt as a dress doesn’t take any effort at all if it’s long enough. Try on the T-shirt first and make sure that it’s long enough for you to feel properly covered and comfortable with wearing it out in public. Keep it simple with a pair of sneakers, or dress it up with a pair of high heel ankle boots.^{[5]
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- Wear an oversized T-shirt with a pair of sandals and simple jewelry—like a pair of small hoops and a basic necklace.
2
Wear a belt around your waist. You can trick anyone (including yourself) into thinking your shirt is actually a dress with the right belt. This is also a great way to add some form to an otherwise formless style. Make sure the belt fits around your waist. You can wear a broad belt or thin, braided belt for a less obvious look.^{[6]
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- Wear an oversized button-up with a braided belt and ballerina flats.
3
Pair it with leggings. Wearing a shirt as a dress can be kind of intimidated if you’re worried about showing too much leg. A great way to stay modest is to wear layer up your look. Wear a pair of leggings and put a tank top on underneath the shirt if it’s a little sheer or you plan to undo some of the buttons.^{[7]
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- Wear a white button-up with black tights and black ballerina flats.

Expert Q&A

Question

How do you wear an oversized shirt without cutting it?

Lauren Schugar
Professional Stylist
Lauren Schugar is a professional fashion and wardrobe stylist. She has worked in the fashion industry for 20 years, and currently specializes in production wardrobes for print and video shoots.

Lauren Schugar

Professional Stylist

Expert Answer

Do a messy tuck in your pants — or whatever bottoms you're wearing — to give yourself a waist.
Question

Is it possible to casually style a tee-shirt with shorts? Would tying it up in a knot by my waist work?

Community Answer

Yes, you can tie it in a knot by your waist.