How to Style an Oversized T-Shirt and Look Polished (for Guys)

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IN THIS ARTICLE

1 Choose a comfortable fit.

2 Let your shirt hang out.

3 Tuck your shirt in.

4 Layer your shirt with a denim jacket.

5 Wear a second shirt on top.

6 Pair with slim pants.

7 Pair with baggy pants.

8 Keep it light and bright.

9 Go sporty with some athletic shorts.

10 Layer with a plaid button shirt.

11 Pair your shirt with a sweater.

12 Throw it back with a retro look.

13 Add some personality with a graphic T-shirt.

14 Go with stripes and patterns.

15 Keep it simple with the plain oversized T-shirt.

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Co-authored by Lauren Schugar

Last Updated: October 1, 2024 Fact Checked

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Oversized T-shirts are back in style and a popular choice for many guys these days. It's a great way to stay cool while showing off your style. There are many simple and trendy ways to wear an oversized t-shirt, but how can you make sure you rock these looks effortlessly? Fear not, we got you covered with this great list of ways you can wear an oversized t-shirt that best suits you.

Steps

1

Choose a comfortable fit.

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1. Pick a shirt that best fits your body type. Looking good is important, but feeling good is as well. Just because your shirt is oversized, doesn’t mean it should be too big for you. The shape and cut is very important. The oversized shirt should be an item in your wardrobe that you can seamlessly rock any day of the week. Being confident and comfortable with your style will make any clothes you wear look even better.

   • The collar of the shirt should fit comfortably without sagging below your neck line.
   • The shoulder seam of the t-shirt should sit right where your shoulders and arms meet.
   • Your sleeves can reach as far as your elbow, but shouldn’t droop past them.
   • The length of your oversized t-shirt should run past your crotch, but stop well before your knees, preferably at your upper thigh.
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2

Let your shirt hang out.

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1. Nothing says casual quite like an untucked t-shirt. This laid back style is perfect for just about any low-key hangout or party. Whether you are wearing pants or shorts, an oversized t-shirt can remain untucked while still remaining fashionable and comfortable. No compromise needed with this look.

   • Your oversized t-shirt can be the focal point of your entire outfit. Let it do all the talking while sporting some classic blue jeans or with chino shorts.
   • Keep a chill vibe with a pair of slick sunglasses that can complete any look that incorporates an oversized t-shirt.

3

Tuck your shirt in.

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1. Reel in the length of your shirt by tucking it in. You can still enjoy the breeziness and comfortableness of an oversized t-shirt while going for a slightly more refined look. Or you can try the semi-tucked look and tuck just the front of your shirt in for a trendier style. Match either tucked in look with a pair of khakis or corduroy pants.

   • You can tuck your oversized t-shirt in while eating out at a restaurant or out while walking through town.
   • Tie your look together with a nice belt that doesn't clash with the oversized t-shirt.
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4

Layer your shirt with a denim jacket.

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1. This hip look is as cool as it is timeless. A denim jacket with an oversized white tee is a classic look that is always in style. The durability of a denim jacket also makes it a valuable clothing item that’ll hang with you for years. This simple yet edgy look is an excellent addition to just about any style.

   • Highlight your denim jacket with a pair of black jeans. This tried and true look can make a great impression for just about any occasion.
   • All white sneakers are an excellent and elegant option to complete this outfit and make your style pop.

5

Wear a second shirt on top.

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1. Pick this combination for an easy and chic look. The double tee has been a mainstay in men's wardrobes for ages, and for good reason. Its simplistic style means that it is perfect for any casual hangout or sporting event. Whether you go with sharp contrasting colors or a subtle complimentary style, this look is as comfortable as it is easy.

   • Proudly sport your favorite team on top as you pair it with your oversized shirt underneath.
   • The classic gray and white t-shirt combination is an easy way to pull off a cool and balanced look.
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6

Pair with slim pants.

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1. This contrasting, trendy look is an easy win. Pairing your oversized t-shirt with slim pants is the best of both worlds, allowing each to shine while they work together. A pair of ripped skinny jeans or some slim fitting workout pants would be great to wear as you head to the movies or head downtown to go shopping.

   • Throw on some sleek sneakers to complete this hip look as you head out to the mall or catch a ball game.
   • Adding a knit hat or baseball cap can go a long way with this breezy outfit.

7

Pair with baggy pants.

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1. The slouchy look is perfect for those lazy days. Lounge pants are a great option to wear with your oversized t-shirt. You can either let your tee hang freely or tuck it inside your pants. A partial or complete tuck offers two unique variations to your look.

   • Sliding on some breezy crocs or comfortable sandals offers a great compliment to this very casual and laid back look.
   • Baggy jeans are another great option to wear with your oversized t-shirt if your lazy day takes you out and about on an impromptu trip.
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8

Keep it light and bright.

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1. Look for colorful oversized t-shirts. During the springtime, the temperatures begin to rise and the sun starts to really shine. Pair your outfit with the season of blooming flowers and lively colors. Whether you’re attending a casual brunch or heading to your favorite winery, oversized t-shirts in pastel colors offer some great style with minimal effort.

   • Experiment with a few different colors as you try and find the style that best fits you. There is a perfect look out there for everyone.
   • A pair of boat shorts or bermuda shorts would make an excellent choice to go with your light colored oversized t-shirt.

9

Go sporty with some athletic shorts.

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1. The oversized shirt and shorts combo is a perfect look for a casual hangout or light workout. With its cool and breezy style, this look is the definition of casual attire. An oversized t-shirt and shorts are also a great way to stay cool during those late summer workouts.

   • Try and wear some sneakers or lightweight sandals to stylishly compliment this cool summer look.
   • Top off your look with a ball cap to complete your outfit as you head to the beach or meet up with some friends at the pool.
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10

Layer with a plaid button shirt.

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1. Go with this hip option during the fall. Nothing says autumn is here quite like the classic plaid button shirt. And paired with an oversized t-shirt and skinny jeans and sneakers? You got yourself a surefire hit.

   • Boots are an excellent footwear option when paired with flannel and jeans.
   • A warm beanie tops off this cozy look as the temperatures fall and the pumpkin spice ramps up.

11

Pair your shirt with a sweater.

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1. Cozy up with this hot style. Whether it's a crew neck or a comfy hoodie, wearing a sweater over the top of an oversized t-shirt is a classic look. You'll look completely chill as you stay warm and stylish during the winter months.

   • When the winter months roll around, a pair of joggers or sweatpants make this outfit the perfect thing to wear around the house.
   • Going to a casual hangout instead? Any pair of jeans would work perfectly with your sweater and oversized t-shirt.
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12

Throw it back with a retro look.

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1. Bring some new cool to that old school style. The strangest thing about fashion is that it works in cycles. And right now, the 80s and 90s are back in style. So turn heads at your next party and show up with some bold colors and baggy jeans.

   • High top sneakers are a great addition to round out any retro style if you’re heading to the arcade or brewpub.
   • A solid pair of sunglasses would be an excellent complementary piece to cap off this vintage fashion statement.

13

Add some personality with a graphic T-shirt.

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1. Let your shirt reflect your personality. Who you are and what you have to say is important. Let your T-shirt become an extension of who you are. There are countless designs, so finding an oversized graphic T-shirt that fits your style should always be within reach.

   • Be as bold or as subtle as you like. Graphic tees are limitless in their creativity.
   • A pair of ripped jeans would go nicely with your oversized graphic T-shirt, adding a touch of edginess to your look.
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14

Go with stripes and patterns.

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1. Show off your style with a little more restraint. Wearing an oversized t-shirt with a trendy pattern is perfect for when your style demands a little more subtlety than a graphic tee while still staying true to your personality. There are countless designs out there, so you’ll never run out of unique shirts that speak to your own personal flair.

   • Pair your striped or patterned shirt with some classic blue jeans or chinos to balance out your look.
   • Joggers are another great option to wear with your oversized shirt when you are looking at a casual or informal hangout session.

15

Keep it simple with the plain oversized T-shirt.

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1. Embrace the oversized t-shirt and wear it alone. Let it be the focal point of your outfit. Its simplicity and casual look means it will go with just about any style of pants or shorts. This look is perfect for lowkey gatherings or just for lounging around.

   • From plain white to mocha brown, there is a color that can match your style and personality.
   • For a bolder style, color coordinate your shoes with your shirt to take your outfit to the next level.
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