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Style Oversized Shirts Without Looking Like a Blanket

Take the stress out by recreating these oversized shirt outfits.
Image credit: @miabrookss; @jessalizzi; @sophiederenzy
  • Image credit: @miabrookss; @jessalizzi; @sophiederenzy

With some favoring the bold statement and others questioning their style, oversized shirts have sparked debates in the world of fashion. However, we cannot deny the fact that these shirts have a nostalgic comeback thanks to social media.

Oversized shirts with a bit of creativity and experimentation offer endless styling possibilities to wear all year, especially during summer. This wallet-friendly choice pairs with multiple pieces so that you create many different outfits for various occasions from professional environment to casual party. 

The trend traced back in the 1920s to flapper style and then in the 1980s it encompassed the oversized shirts as a rebellion against fitted clothing. This attire again appeared on the canvas of trends in 1990s hip-hop culture. 

It gained traction in 2010 when celebrities like Rihanna and Kanye West wore oversized outfits. Along with that, the comfort, inclusivity, body positivity, and stylish availability in all sizes made oversized clothing a popular wardrobe staple.

However, the beauty of these shirts is to wear them according to the moment to make a big difference in your overall look. 

For instance, wear lightweight and breathable cotton, linen, or rayon fabrics for a beach day, casual outings, running errands, or when hanging out with friends and family. Likewise, if you are heading to a formal event or date night then choose oversized shirts with silk or satin and consider the weight and drape of the fabric.

There are numerous ways to style an oversized shirt and are worn by anyone regardless of body type. If you prefer a fitted look, add a piece of jewelry or belt to create a cinched waist. For a more polished look tuck in your oversized shirt in pants or dark skirts.

Many fashion icons have embraced the oversized shirt looks and if you want to recreate the same look. Ahead, see the best classic outfits to recreate now.

Outfit #1

Outfit is: Light blue oversized button-up shirt + White maxi skirt + Black heeled sandals + Black sunglasses

My note: Do you know those unbearably hot summer days when picking an outfit feels like a chore? Don’t worry. Keep it easy and go for a light blue oversized button-up shirt paired with a white maxi skirt, black heeled sandals, and a pair of black sunglasses.

Outfit #2

Outfit is: White button-up shirt + Gray crewneck T-shirt + Light blue denim cutoff shorts + Olive green sneakers with white socks + Oversized yellow-tinted sunglasses + Beige tote bag

My note: Looking for a laid-back yet versatile outfit that works from day to night? Consider the combo above. A white button-up shirt layered over a gray crewneck T-shirt, paired with light blue denim cutoff shorts and olive green sneakers, will keep you comfortable during the day and still look good as the evening cools down.

Outfit #3

Outfit is: Bright green oversized button-up shirt + Black mini skirt + Black knee-high boots + Orange quilted crossbody bag + Clear glasses

My note: Just because bright green isn’t the “trendy” color of the moment doesn’t mean it can’t be on point; take the outfit above as an example. The easiest way to make this color feel fresh is by choosing bold pieces like an oversized button-up shirt paired with a black mini skirt and knee-high boots for the perfect summer look.

Outfit #4

Outfit is: Light blue striped oversized button-up shirt + Gray high-waisted trousers + White wide belt with double buckles

My note: This color might often seem plain, but that’s just because you haven’t found a fun way to style it yet. I encourage anyone hesitant about this hue to give the look above a try. Pair a light blue striped button-up shirt with gray high-waisted trousers and a white wide belt with double buckles, and see if you still feel the same way. (I’m betting you won’t.)

Outfit #5

Outfit is: White oversized button-up shirt + White high-waisted shorts with a black belt + Black sandals + Woven straw crossbody bag + Black sunglasses

My note: Not to sound repetitive, but is there any easier way to nail a look than with an all-white outfit? Nothing beats pairing a white button-up shirt with white high-waisted shorts, a black belt, black sandals, a woven straw crossbody bag, and a good pair of black sunglasses—it’s truly the perfect summer combo.

Outfit #6

Outfit is: Light blue oversized button-up shirt + White maxi skirt + Blue sneakers + Beige baseball cap + Brown woven hobo bag + Gold layered necklaces

My note: Consider this your reminder that there’s no better way to embrace a laid-back summer vibe than with a light and breezy look like the one above. You may not be strolling along a coastal boardwalk, but with a light blue oversized button-up shirt, a white maxi skirt, blue sneakers, a beige baseball cap, a brown woven hobo bag, and gold layered necklaces, you’ll feel like you just stepped off a sun-soaked pier.

Outfit #7

Outfit is: White oversized button-up shirt + Light blue jeans + Black pointed-toe flats + Black sunglasses + Black leather crossbody bag

My note: For those late summer days when the heat finally begins to ease up, there’s no need to pack away your light pieces just yet. You can transition these items into the cooler months by choosing versatile options like the outfit above. A white button-up shirt and light blue jeans work well now with black pointed-toe flats, and later, you can easily layer them with boots and a jacket. Forget the rules and enjoy experimenting with this classic look.

Outfit #8

Outfit is: Blue striped oversized shirt + Beige mini skirt with red drawstring belt + Black ankle boots + Red patent leather shoulder bag + Gold necklaces

My note: Reminder: You don’t have to wear head-to-toe blue to make a statement with this color. Style a blue striped button-up shirt with your favorite beige mini skirt, black ankle boots, and a red patent leather shoulder bag. Do this, and you’ll capture that effortless vibe that’s always in style.

Outfit #9

Outfit is: White striped oversized button-up shirt + Light blue high-waisted jeans + White loafers + Beige handbag + Round sunglasses

My note: I have to admit that anything too casual usually doesn’t fit my idea of a put-together look, but the outfit above is an exception I didn’t see coming. Who would have thought that a simple white striped button-up shirt with light blue high-waisted jeans and white loafers could pull off such a look?

Outfit #10

Outfit is: Blue striped oversized button-up shirt + Black wide-leg trousers + White sneakers + Black leather crossbody bag + Black sunglasses

My note: Honestly, I can’t think of better proof of the power of this combo than the outfit above. A blue striped oversized button-up shirt paired with black wide-leg trousers and white sneakers might seem straightforward, but it’s undeniably on point.

Outfit #11

Outfit is: White oversized button-up shirt + Black and white striped wide-leg pants + Black crossbody bag + Black sandals + Black sunglasses + Gold cuff bracelet

My note: Are you one of those people who can’t quite commit to an all-white outfit? I get it—maybe you’re worried about spills or just prefer a bit more contrast. An easy way to break up the white is by pairing it with other neutrals—like the white button-up shirt above styled with black and white striped wide-leg pants and matching accessories.

Outfit #12

Outfit is: White bikini top + Cream crochet maxi skirt + Beige oversized button-up shirt + Wide-brim straw hat + Straw tote bag

My note: One of the easiest ways to elevate this look is through layering. Try styling a beige oversized button-up shirt over your white bikini top and cream crochet maxi skirt. Add a wide-brim straw hat and a straw tote bag—it’s a laid-back formula that’s sure to make this outfit feel complete.

Outfit #13

Outfit is: Light blue striped oversized button-up shirt + White wide-leg pants + White tube top + Beige quilted handbag + Beige pointed-toe heels + Gold bracelets + Round sunglasses

My note: While it’s easy to wear the light blue striped button-up shirt on its own, consider trying something more creative like the outfit above. Layering it over a white tube top with white wide-leg pants and adding beige pointed-toe heels will give this classic shirt a fresh twist. Finish the look with a beige quilted handbag, gold bracelets, and round sunglasses for that extra touch.

Outfit #14

Outfit is: Blue striped button-up shirt + Black wide-leg pants + Burgundy oversized shoulder bag + Burgundy sandals + Black sunglasses

My note: If it’s not already obvious, let me emphasize: The secret to elevating any button-up shirt lies in the accessories. While it’s always good to keep up with seasonal trends, you can’t go wrong with timeless pieces—like a burgundy oversized shoulder bag, matching sandals, and black sunglasses.

Outfit #15

Outfit is: Red and white striped oversized button-up shirt + Light blue denim cutoff shorts + Black loafers with white socks + Straw shoulder bag + White oversized sunglasses

My note: While pairing a button-up shirt with standout accessories is a simple way to make it shine, it’s not the only way to create a memorable look. Take inspiration from the outfit above by styling a red and white striped oversized button-up shirt as a light layer over your light blue denim cutoff shorts.

Outfit #16

Outfit is: Light blue oversized button-up shirt + White pencil skirt + Black flip-flops + Black handbag + Black sunglasses + Gold earrings

My note: You don’t need bold prints to make this outfit stand out—just look at the ensemble above. By pairing a light blue button-up shirt with a white pencil skirt and black accessories, you’ll give this classic combo a fresh and updated feel.

Outfit #17

Outfit is: Yellow oversized button-up shirt + Light blue high-waisted jeans + Black heeled sandals + Black handbag + Black sunglasses

My note: If you want to make this staple feel more personalized to your style, start by adding layers. Whether it’s a blazer, a lightweight jacket, or a cardigan on top, the addition of a top layer will transform this yellow button-up shirt and light blue high-waisted jeans combo in no time.

Outfit #18

Outfit is: Light blue oversized button-up shirt + Gray high-waisted trousers + Beige pointed-toe heels + Black mini handbag

My note: Why not get a bit more creative with your styling? Instead of sticking to the usual combinations, try tucking your light blue button-up shirt into gray high-waisted trousers. It’s a great way to reinvent the look, plus it makes the outfit more versatile for different occasions.

Outfit #19

Outfit is: Black wrap bikini top + Beige drawstring linen pants + White oversized button-up shirt + Black sunglasses

My note: If trying new styling combos feels daunting, consider going for a coordinated look. Pairing a white oversized button-up shirt with beige drawstring linen pants is an easy way to give your black wrap bikini top a fresh twist without any extra effort.

Outfit #20

Outfit is: White oversized button-up shirt + White high-waisted shorts + Round sunglasses

My note: Want to take this classic piece from day to night? Try pairing a white button-up shirt with white high-waisted shorts and round sunglasses for a clean, effortless look that works for any occasion. It’s a simple combo that can be easily dressed up or down depending on your plans.

Outfit #21

Outfit is: Blue striped oversized button-up shirt + Beige mini skirt + White slingback heels + Black clutch + Black sunglasses + Gold hoop earrings

My note: One of the easiest ways to keep this classic piece from feeling “stale” is by pairing it with accessories that are trending each season. For instance, during the summer, you can style the blue striped button-up shirt with a beige mini skirt, white slingback heels, and gold hoop earrings. As the seasons change, swap out the sandals for boots or layer with outerwear to keep the look fresh and current.

Outfit #22

Outfit is: White puff-sleeve oversized shirt + Black straight-leg pants + Red sandals + Red beaded necklace + Black shoulder bag

My note: No matter what styles are trending, classic pieces like the white puff-sleeve button-up shirt remain a go-to season after season. There’s no outfit formula as reliable as pairing it with black straight-leg pants, red sandals, a red beaded necklace, and a black shoulder bag. This combination is timeless and effortlessly pulled together.

Outfit #23

Outfit is: Blue striped oversized button-up shirt + Light blue wide-leg jeans + Black and white Mary Jane flats + Beige quilted handbag + Black sunglasses

My note: While blue striped button-up shirts are a summer staple, they’re not always the easiest to style for a polished look—until now. Use the outfit above as your guide by pairing your shirt with light blue wide-leg jeans, black and white Mary Jane flats, a beige quilted handbag, and black sunglasses. This combo strikes the perfect balance between laid-back and refined.

Outfit #24

Outfit is: Champagne satin oversized shirt + White skinny jeans + Tan mule sandals + Gold earrings + Black sunglasses

My note: If it’s too warm to wear a full-sleeve cotton shirt, consider taking a cue from the outfit above. Pairing a champagne satin button-up with white skinny jeans and tan mule sandals is the ideal way to stay cool while still looking put together. Finish the look with gold earrings and black sunglasses for that effortless summer vibe.

Outfit #25

Outfit is: Black oversized button-up shirt + Black and white striped wide-leg pants + Black sandals + Black straw handbag + Black sunglasses + Gold bangles + Gold earrings

My note: Besides opting for lightweight fabrics, you can stay comfortable during those in-between months by focusing on your outfit’s layering. When it’s not too hot outside, style a black button-up shirt with black and white striped wide-leg pants to keep things breathable yet covered. Add black sandals and accessorize with gold bangles and earrings to ensure you’re fully prepared for whatever the weather brings.

Outfit #26

Outfit is: White oversized shirt + White high-waisted shorts + Brown sandals + Straw tote bag + Black sunglasses + Gold hoop earrings + Brown watch

My note: If you lean towards a minimalist style, you don’t need to add bold colors to make your white button-up shirt and high-waisted shorts combo stand out. For the same effect, try pairing it with thoughtful accessories like gold hoop earrings, a brown watch, and a straw tote bag.

Outfit #27

Outfit is: Pink satin leopard print oversized shirt + Light blue denim cutoff shorts + White platform sandals + White shoulder bag

My note: Keep your look ultra-minimal by narrowing down your color palette, silhouettes, and accessories. Opt for a pink satin leopard print button-up shirt styled with light blue denim cutoff shorts and white platform sandals. In this case, less really is more—let the bold print and simple accessories do all the talking.

Outfit #28

Outfit is: Light blue oversized button-up shirt + Brown bikini top + Cream crochet pants + Black sunglasses + Gold hoop earrings

My note: To strike the perfect balance between simplicity and standout pieces, it’s important to focus on the silhouette of your outfit just like above.

Outfit #29

Outfit is: Mint green oversized button-up shirt + Light blue straight-leg jeans + Green heeled sandals + Green mini handbag + Black sunglasses

My note: Perfect for the day at corporate or Sunday brunch.

Outfit #30

Outfit is: Cream oversized knit sweater + Green tie-dye wide-leg pants + Beige sandals + Black sunglasses

My note: Consider this your second & last reminder that button-up shirts can be styled for any occasion, even casual summer outings! Make this look stand out by pairing a mint green button-up shirt with light blue straight-leg jeans, green heeled sandals, and a matching mini handbag. Complete the outfit with black sunglasses for a fresh, cohesive summer ensemble.

Erma Sanches has been following & covering fashion trends for 5 years. She’s a certified Fashion Analyst in Philadelphia. She has been also writing about latest fashion, covering runway, and new finds for past 7 years now. Erma has been covering fashion for 10 years and writing professionally for 7 years. She worked at Delicious Boutique, a boutique in Philadelphia, for one year. In 2018, she completed her Fashion Analyst training and earned her certification in 2020. Erma joined YouDoYourWay Media Publication in 2023 and now covered more than 100 content pieces. Erma graduated from the University of Michigan with a a Bachelor of General Studies in english writing and a Bachelor of Arts.

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