Oversized shirts are particularly on trend right now. However, they can be tricky to pull off, adding unwanted width or bulk depending on how you wear them. Take a look below at how to style an oversized shirt for the most flattering look…
oversized shirts you can choose
Before looking at how to style one, let’s take a look at some of the most stylish oversized shirts you can choose.
Susanne @textelle above (read her style interview here) opts for a color block outfit in yellow and pink. She breaks up the width of her shirt by wearing a few buttons open at the bottom.
Recreate her outfit with this similar shirt, trousers and heels.
oversized silk shirt
A silk shirt is always a wardrobe classic that won’t go out of style. You could wear this with skinny jeans or leggings, or tucked into wider pants, making it a great option when thinking about how to style an oversized shirt.
print shirt
Opt to make your oversized shirt the statement piece of your outfit by choosing a print like the shirt (below) from COS.
amazon shirt
Reviewers of the Minibee shirt from Amazon (below) say it is the ideal tunic length to wear with leggings, and is cut in such a way that it is not boxy.
Minibee button down tunic blouse
Menswear inspired from Club Monaco
Oversized shirts are inspired by menswear, so you could take this idea further by choosing a design which nods to a man’s work shirt.
Club Monaco button-up shirtdress
black shirt
Just as white is always on trend, so too is a black oversized shirt. The & Other Stories shirt (below) has a flattering deep v-neck as well as interesting tie sleeves.
& Other Stories relaxed cuff tie blouse
oversized tee
Of course, you don’t have to opt for a traditional button down. You could choose an oversized t-shirt.
4th & Reckless oversized shirt
Oversized poplin shirt
Another striped option for you, the poplin shirt (below) from Favorite Daughter could be worn for work or with jeans for a casual look.
Favorite Daughter poplin shirt
How to wear your oversized shirt
Now that you’ve chosen your favorite oversized shirt, what should you wear it with?
With leggings or skinny jeans
Wearing your oversized shirt with leggings or skinny jeans is always a good idea as it adds balance to your outfit. The shirt is loose but the bottoms are tighter, ensuring your outfit doesn’t look wide all over.
Sharryn @thestylishwoman above (read her style interview here) looks stylish and casual in her oversized shirt worn with high-top sneakers and accessorized with a headband and red lipstick.
Steal her look with this similar shirt, pants, sneakers and head wrap.
COS printed silk blouse – Good American skinny jeans – Bella Vita sandal – See by Chloé leather wallet on a chain – Panacea geometric hoop earrings
with a shorter jacket
This is a good way to hide a belly as the different lengths of the top and the jacket confuse the eye. This is also a good technique for making your legs look longer. Even though the shirt finishes further down your thighs, the jacket stops at your waist. That visually shortens your torso and lengthens your legs.
COS cropped denim jacket – COS silk oversized shirt – Max Mara Leisure rib knit pants – Jeffrey Campbell slide sandal – Nordstrom leather clutch – Jane Basch Designs hoop earrings
With a belt
If you want to define your waist, or you just want to wear your oversized shirt in different ways, a belt is always a good accessory.
There are more tips and tricks to get the most out of your belt as an accessory in this article.
& Other Stories relaxed cuff tie blouse – Good American skinny jeans – MIA espadrille wedge sandal – Tory Burch leather crossbody bag – Treasure & Bond braided leather belt – Jane Basch Designs hoop earrings
Tucked in (or half tucked)
By tucking in part of your shirt, it allows your waistline to be seen, while adding a nonchalant look. Adaline @sdmomstyles above shows how you could style the half tuck.
Note that wearing shoes in a similar color to her skintone has a leg-lengthening effect.
Steal her look with this similar shirt, denim shorts, loafers and belt.
4th & Reckless oversized shirt – Madewell vintage jeans – Tommy Hilfiger sneaker – See by Chloé leather wallet on a chain – Panacea geometric hoop earrings
inspired by MENSWEAR
If you’ve opted for a menswear inspired shirt, you could keep this theme through the rest of your outfit with a pair of smart pants and loafers.
Club Monaco button-up shirtdress – Anne Klein flare leg pants – Franco Sarto loafer – Nordstrom leather clutch – AllSaints linear chain necklace
Layered with a top over
Think differently when it comes to your layering. Try wearing your vest top over your shirt. This works best when your vest has thick straps and stops at, or above, your waistline.
Madewell sweater tank – COS silk oversized shirt – Madewell high waist jeans – Franco Sarto loafer – See by Chloé leather wallet on a chain – AllSaints linear chain necklace
As a dress
You could go with the ultimate oversized shirt look and wear a shirt dress. Angela @angelamashelle above looks fabulous in her long shirt. If you prefer a longer length, you could choose a knee-length, midi or maxi option.
Get her look with this similar shirtdress, sandals, bag and earrings.
Nordstorm Signature silk shirtdress – Jeffrey Campbell slide sandal – Tory Burch leather crossbody bag – Jane Basch Designs hoop earrings
with leather pants
For a rock chick vibe, you could always choose a pair of edgy leather pants with your long shirt. Your bottom will be covered and just your legs on show.
4th & Reckless oversized shirt – Felina sueded croc embossed leggings – Marc Fisher LTD block heel pump – Nordstrom leather clutch – AllSaints linear chain necklace
Breaking the “rules” with wide pants
While it’s harder to wear wide with wide, that doesn’t mean it can’t be done. You can wear your wide shirt with a pair of wide pants and still create a stylish effect.
Dayle @artfulcitystyle above (read her style interview here) shows how you could do this. You’ll see that the addition of wedge heels ensures her legs still look long.
Recreate her outfit with this similar striped shirt, wide leg pants and sandals.
Favorite Daughter poplin shirt – Joe’s bootcut jeans – MIA espadrille wedge sandal – Tory Burch leather crossbody bag – Jane Basch Designs hoop earrings
How to style an oversized shirt: As a swimsuit cover-up
A long shirt is a great item to pack for your vacation as you can wear with your pants or shorts as well as over your swimsuit as a beach cover-up.
Minibee button down tunic blouse – Boden swimsuit – Revitalign flip flop – LIVACASA beach bag
Your oversized shirt outfits together in one capsule
Below, you can see all of the outfits from above together in one oversized shirt capsule. You could definitely mix and match to get several different looks.
shop all items above here:
Best places to buy oversized shirts
- COS
- Stella Carakasi
- Ellazhu (Amazon)
Continue reading:
- The Ultimate Checklist Of Wardrobe Essentials: Which 33 Essential Pieces Do You Need In Your Closet?
- How To Wear Tunics Or Short Dresses With Pants
- The Best Tops To Hide Your Tummy
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Feature image by Sharryn @thestylishwoman
Sylvia is 40+style’s editor-in-chief and has been helping women find their unique style since 2011. An alumni of the School of Color and Design, she is devoted to empowering women of any age to look and feel their best. Read more about Sylvia and 40+style on this page.
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