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How to Style a Relaxed Fit T Shirt |Drunk Tees

by Chiranjeev Singh on Sep 28, 2026
How to Style a Relaxed Fit T Shirt |Drunk Tees

How to Style a Relaxed Fit T Shirt

You've probably noticed it.

T shirts are getting looser. More room through the body. Longer sleeves. Relaxed shoulders. That effortless “I just threw this on” kind of look that somehow looks cooler than an outfit you spent an hour putting together.

But here's the thing.

You don't need a specially designed oversized t shirt to get that relaxed look.

Sometimes, all you need is the right fit, the right size and a little bit of confidence.

At Drunk Tees, we make unisex t shirts from XS all the way to 7XL, so there's plenty of room to find the fit that feels right for you.

Whether you like your tee sitting closer to the body or prefer something with a little more breathing room, let's get into it.

What Is a Relaxed Fit T Shirt?

A relaxed fit t-shirt gives you a little more room than a traditional regular fit.

There's more space through the body, the sleeves have a little more freedom and the overall silhouette feels comfortable without looking like you've borrowed someone else's clothes.

A regular fit generally follows your natural shoulder line and sits closer to the torso.

A relaxed fit gives you more room to move.

And then there's the deliberately loose look, which you can create simply by sizing up.

They're all different ways of wearing the same basic piece.

The trick is figuring out what feels like you.

Regular Fit vs Relaxed Fit

This isn't really about body type.

It's about proportion and personal preference.

A regular fit t-shirt works beautifully with wider trousers, cargos or loose denim because the closer fit on top gives the outfit some structure.

A relaxed fit gives you a little more freedom. Pair it with straight jeans, tapered joggers or shorts and you've got an easy everyday look without looking like you're trying too hard.

And if you want an even looser silhouette, simply go up a size.

That's one of the easiest ways to change the way a t- shirt sits on your body without completely changing your wardrobe.

How to Style a Relaxed Fit T Shirt

This is where things get interesting.

With Jeans

You really can't go wrong here.

A relaxed graphic tee with straight or slim jeans gives you an easy balance. There's enough room up top while the jeans keep the overall silhouette clean.

Want something more streetwear?

Try cargos or wider denim.

The key is contrast. If the tee is loose, keeping the bottom half a little more structured can stop the whole outfit from becoming one giant cloud of fabric.

Unless that's exactly what you're going for.

In which case, carry on.

With Joggers

The relaxed tee and joggers combination is basically a love letter to comfort.

Go for tapered joggers if you want a cleaner look. The roomier tee gives you freedom up top while the tapered ankle keeps the outfit from looking shapeless.

Add sneakers.

Maybe a cap.

Maybe a watch.

Done.

You don't need a fashion degree for this.

With a Jacket or Overshirt

This is one of the easiest ways to add some structure to a relaxed fit.

Throw on a denim jacket, bomber, flannel or open overshirt and you've instantly got more definition.

The tee stays comfortable while the outer layer gives the outfit some shape.

It looks considered without looking like you tried too hard.

Which is usually the sweet spot.

With Shorts

Perfect for warm weather.

A relaxed graphic tee with denim shorts, cargo shorts or fitted shorts is an easy combination for weekends, holidays, road trips or those days when the weather decides it has had enough of you.

Finish it with sneakers or slides and you're good.

Styling Relaxed Fit T Shirts for Men

For men, one of the easiest things to get right is the length.

A relaxed t-shirt should have enough room to feel comfortable without drowning your proportions.

If you've sized up, pay a little attention to where the hem falls.

If it gets too long, try a simple front tuck.

You can also roll the sleeves once if they feel a little loose. It's a tiny adjustment, but it can make the entire outfit feel more deliberate.

Pair it with straight trousers, jeans, cargos or joggers.

Add sneakers.

Maybe a simple chain or cap.

And stop there.

You don't need twelve accessories to prove you have style.

Styling Relaxed Fit T Shirts for Women

Relaxed fit t-shirt are ridiculously versatile.

Wear one with high waisted jeans and tuck the front in.

Pair it with denim shorts.

Wear it with bike shorts.

Layer it over a slip dress.

Or tuck it into wide leg trousers and add a belt for something a little more polished.

You can completely change the silhouette just by changing what you do with the bottom half.

Tuck it.

Knot it.

Leave it loose.

Layer it.

Same tee.

Completely different outfit.

Relaxed Fit T Shirt Outfit Ideas

Looking for somewhere to start?

Here are a few combinations that are hard to mess up.

Everyday: Relaxed graphic tee, straight jeans and sneakers.

Gym to street: Relaxed tee, tapered joggers, sneakers and a cap.

Streetwear: Graphic tee, cargo pants, sneakers and an open overshirt.

Weekend: Relaxed tee, denim shorts and slides.

A little smarter: Tee tucked into tailored trousers with a structured jacket and clean sneakers.

The common thread?

Balance.

Something loose with something structured.

Something casual with something a little sharper.

That's what makes an outfit feel intentional rather than accidental.

Want a Looser Look?

This is where sizing comes into play.

At Drunk Tees, our t-shirts are available from XS to 7XL.

So if you normally wear an M and want a little more room, you can try an L.

Normally wear XL?

Try XXL for a more relaxed silhouette.

It's not complicated.

You're simply choosing how you want your tee to sit.

Your usual size for a more natural fit.

One size up for more room.

And if you like your tees really roomy, you can go further.

That's the beauty of having options all the way up to 7XL.

A Few Things That Can Throw Off the Look

There is a "relaxed fit”.

And then there's “did you borrow that from your older brother?”

The difference usually comes down to a few simple things.

Going loose everywhere. A relaxed tee with very loose trousers can work, but it takes a little more styling. If you're just getting into the look, keep one part of the outfit more structured.

Ignoring the shoulders. If you've sized up, make sure the shoulder still sits comfortably. A little drop is fine. Too much can make it look like you simply picked the wrong size.

Forgetting about length. A little extra length works well. Too much can throw off the proportions.

Doing too much everywhere else. A good graphic tee already has a personality of its own. You don't need ten accessories competing for attention.

Sometimes the tee should just be the tee.

The Real Trick?

Don't overthink it.

That's probably the biggest secret to dressing well.

Wear something comfortable.

Find proportions that work.

Add a couple of things that actually feel like you.

Then get on with your day.

Clothes aren't supposed to make you spend half your morning wondering whether the outfit is working.

They're supposed to let you live in them.

Go out.

Ride somewhere.

Meet your people.

Have a few drinks.

Make questionable decisions.

Come home.

Throw the tee in the wash.

And wear it again.

That's what a good t shirt is supposed to do.

FAQs

Do Drunk Tees sell oversized t-shirts?

Not specifically. Drunk Tees currently offers unisex regular and relaxed fit t-shirts in sizes XS through 7XL.

Can I get a looser look with a Drunk Tees t-shirt?

Absolutely. If you normally wear a particular size, going one size up can give you a roomier, more relaxed silhouette.

What sizes does Drunk Tees offer?

Our t-shirts are available from XS to 7XL.

Because good designs shouldn't come with a size limit.

Can relaxed fit t shirts work for every body type?

Yes. The important thing is finding the size and proportions that feel comfortable and look right to you.

What can I wear with a relaxed fit t shirt?

Pretty much everything you'd expect from a good everyday tee. Jeans, cargos, shorts, joggers, trousers, jackets and overshirts all work.

The rules aren't complicated.

Find your fit.

Find your style.

Then make it yours.

Drunk Tees.

Soul Wear.

Tags: T-Shirt
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T-Shirt Size Chart & Fit Guide | Drunk Tees
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