How to Wear Oversized Shirts

Vogue was all about oversized shirts this October – they even mentioned them on the front cover.  If Vogue says they can look fierce, then they definitely can… but only if they’re worn the right way.

Easy enough, right?  No, not quite.

Here’s the issue: figuring out how to compose an outfit with an oversized shirt can be frustrating and even downright impossible.

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Every time I put one on, I go through the same process.

  1. I question what on earth can even be done with so much extra fabric.
  2. I wonder whether, when left alone, the shirt looks fashionably flowy or like a potato sack.
  3. I try to determine what I should do with the sleeves, but I can’t seem to make up my mind.
  4. I mess around to see if the top needs to be tucked in, knotted, tied up with a scrunchie, or belted [like a dress].
  5. I likely proceed change my pants to match the style I’ve chosen – only to switch back to the ones I was wearing initially.
  6. I continue to toy around with the oversized shirt in each style, and I continue to fail.

When I’m done, the fabric looks crumpled and exhausted, essentially matching how I’m feeling by that point.  With all of those crinkles, it’s already past wrapping a belt around – so I yank off that oversized shirt and settle for something I didn’t plan on wearing… yet again.


It’s too bad that no one really tells us what on Earth to do with these enormous fashion enigmas.  It always looks so easy to wear them in the media, but figuring out oversized shirts in real life is miserable.

That’s why I’ve given it some serious thought and crafted this guide – so that we can have oversized shirts back in our lives with all of the style, and none of the misery. 

When to tuck it in

If you have a tiny bit of extra fabric, but less than a fistful of it, tuck the shirt in.  You won’t really be able to do anything else with it – there’s not enough fabric to knot, tie, or belt it, and it may look funky left alone.

Should you decide to tuck it in, you’ll want that something it’s tucked into (pants, shorts, or skirt) to be mid-rise or high-waisted.

If you love belts, then you’re in luck – this style looks great when belted.

Don’t forget to cuff the sleeves – you’ll probably want to for this look.

When to knot it

Just to clarify, when I say “knot it”, I mean tying up the shirt without using any type of a tie.  This is when you literally twist the shirt into itself to create a simple knot from its own fabric.

These knots generally look best in the front of your torso, whether that’s centered or slightly off to the side.

Knotting the shirt is best when there’s a little bit of extra cloth, since it’s still too much to be tucked in without causing fabric lumps and not enough for it to stay put in a tie.

If it seems to be somewhere in between “tucked in” and “tied up”, then go ahead and knot away – it should work out pretty well.

Consider rolling up your sleeves, depending on the style of shirt.

When to tie it

When it’s not long enough to be a dress and too thick or coarse to be knotted up, then use a hair tie or scrunchie to tie it.

Make sure you tuck the tail into the back of your shirt so that your figure doesn’t get any strange bumps from the gathered fabric.  Atleast if the shirt bulge is in the back, it’ll be clear that you just tied up your shirt – and that’s perfectly chic.

When you’re tying it, you may want to cuff your sleeves if the sleeves are very long – this creates a more unified look.

When to belt it [like a dress]


A good rule of thumb for knowing when to wrap a belt around your oversized shirt is asking yourself if it can pass as a dress in length [or as a potato sack].  If you decide that it can, then it’s probably safe to go with a belt at the waist.

If you’re belting it, then rolling up your sleeves is advisable.  Cuffed sleeves go brilliantly with belts.

For cold weather, belted oversized shirts are perfect to wear over skinny jeans or leggings.

Don’t forget the boots!

When to wear it as is

This one is really a judgment call scenario – if you pull on that oversized shirt and like it as is, then you’re done.  Don’t tuck it, knot it, tie it, or belt it – just let it be if it already works on its own.

If it’s pretty long and you’re somewhat nervous that it may actually still be a potato sack, then belt it just to be safe.

Oversized shirts are important style pieces, even if we “forget about” (avoid) them all too often.

But there will be no more of that – now is the time to stop being afraid of them and take our wardrobes back.

I know that the thought of looking like a scrunched up potato sack is terrifying, but the leap has to be made if we want to stop letting oversized shirts ruin our lives.

Just remember – Vogue still likes them.  That has to count for something, right?




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