Oversized shirts are having a major moment right now, and it’s easy to see why. This trend effortlessly combines a great look with unbeatable comfort, making it a go-to choice for fashion lovers everywhere.
Whether you’re rocking a graphic tee or a classic button-down, an oversized shirt offers that perfect blend of laid-back vibes and stylish flair. But let’s be real – while the fit may lean casual, it’s important to style these pieces properly to avoid looking like you just rolled out of bed.
That’s why I’ve put together this ultimate guide on how to style an oversized shirt, featuring 20 street-style-inspired looks that’ll have you turning heads wherever you go. So, keep scrolling to discover fresh ways to rock this versatile wardrobe staple!
1. Classic Stripes and Wide-Leg Trousers
Let’s kick things off with a timeless combo that never fails to impress. Picture this: an oversized blue and white striped button-down shirt paired with crisp white wide-leg trousers. This look screams “effortlessly chic” and is perfect for those days when you want to feel put-together without trying too hard.
I love how the vertical stripes on the shirt create a lengthening effect, while the wide-leg trousers add a touch of sophistication. This outfit works for a casual day at the office or a weekend brunch with friends.
2. Denim Shorts and Knee-High Boots
Ready to take your oversized shirt game up a notch? Try pairing an oversized white button-down with distressed denim shorts and gray suede knee-high boots. This trendy oversized button up shirt outfit is all about contrasts – the slouchy shirt against the fitted shorts, and the casual denim paired with sleek boots.
Add a black crossbody bag and round sunglasses to complete this street-style-ready look. I always recommend rolling up the sleeves of your oversized shirt for a more relaxed vibe.
3. Graffiti Prints and Mini Skirt
For those days when you’re feeling bold, reach for an oversized button-down shirt with graffiti-style prints. Layer it over a blue crop top and pair with a denim mini skirt for a fun, youthful look.
White ankle boots and slim sunglasses add a touch of edge to this outfit. This is one of those oversized shirt outfit ideas that really lets you express your personality through your clothes.
4. Pink Shirt and White Trousers
Who says oversized shirts can’t be feminine? An oversized pink button-down shirt paired with high-waisted white wide-leg trousers creates a soft, romantic look that’s perfect for spring or summer.
Add a thin brown belt to cinch in your waist and define your silhouette. White sneakers keep the outfit casual, while white-framed sunglasses and a small brown handbag add those all-important finishing touches. This casual oversized white shirt outfit (with a pink twist!) is one of my favorites for its versatility.
5. Striped Shirt and Black Mini Skirt
Here’s another way to rock stripes: pair an oversized red and white striped button-down shirt with a black mini skirt. This combination is perfect for a casual date night or a day out shopping with friends.
Add a white baseball cap for a sporty touch, and black pointed-toe kitten heels to elevate the look. I love how this outfit balances casual and dressy elements.
6. Summer Stripes and Denim Shorts
Speaking of stripes, here’s a summer-ready version of the oversized shirt and skirt outfit. Start with a red and white striped oversized shirt and pair it with denim shorts.
White sandals keep things cool and comfortable, while white sunglasses and a small white handbag add a crisp, clean finish to the look. This outfit is perfect for beach days or casual summer outings.
7. Navy Monochrome and Knee-High Boots
For a sophisticated take on the oversized shirt trend, try a monochrome look with an oversized navy shirt and matching navy shorts.
Brown knee-high boots add an unexpected twist and make this outfit suitable for transitional weather. This look proves that oversized shirts can be sleek and put-together.
8. Pinstripes and Denim Skirt
Combine business and pleasure with an oversized white pinstriped shirt paired with a white denim long skirt. A beige baseball cap adds a casual touch, while a white shoulder bag keeps things coordinated.
This outfit is perfect for those “casual Friday” vibes or weekend errands when you want to look polished but feel comfortable.
9. Shirt Dress and Beach Accessories
Take your oversized shirt to the beach by opting for a blue and white striped shirt dress. Layer it over a white bikini top for a chic cover-up look. Add a straw hat, sunglasses, and a blue handbag to complete this vacation-ready ensemble.
I always recommend a shirt dress for those days when you want the oversized shirt look with minimal effort.
10. White Shirt and Classic Denim
You can’t go wrong with a classic oversized white button-down shirt paired with light wash jeans. Add a black belt to define your waist, and accessorize with a black handbag, black shoes, and sunglasses for a timeless look.
This is one of those casual oversized white shirt outfits that you’ll find yourself reaching for again and again.
11. Blue Shirt and Dark Jeans
For a fresh take on denim-on-denim, try a light blue oversized button-down shirt with wide-leg dark blue jeans. A woven handbag adds texture, while white strappy heels dress up the look. Dark sunglasses give it that cool-girl finish. This outfit is perfect for a casual office environment or a weekend lunch date.
12. Denim Layers and Wide-Leg Pants
Layer a blue denim oversized shirt over a black and white striped top for an interesting play on textures and patterns. Pair with black wide-leg pants and chunky black sandals for a comfortable yet stylish look.
A small black crossbody bag is all you need to complete this outfit. I love how this look combines multiple trends in one cohesive ensemble.
13. Gray Shirt and Light Wash Jeans
Don’t overlook the power of a gray oversized button-down shirt. Pair it with light wash straight-leg jeans and white pointed-toe heels for a look that’s both comfortable and polished.
A small black handbag adds just the right amount of contrast. This is one of those oversized shirt outfit ideas that works for various occasions, from office to weekend.
14. White Shirt and Blue Jeans
An all-white look is always a showstopper. Pair a white oversized button-down shirt with blue jeans and white pointed-toe heels. Dark sunglasses add a touch of mystery and glamour. This outfit is perfect for those days when you want to feel fresh and put-together.
15. White Shirt and Beige Trousers
For a sophisticated take on casual, pair an oversized white button-down shirt with beige wide-leg trousers. White sneakers keep the look grounded, while a small handbag adds a polished touch. This outfit is perfect for running errands or casual Fridays at the office.
16. Green Monochrome and Chunky Sneakers
Make a statement with an oversized green shirt layered over a white crop top and paired with matching green shorts. Chunky white sneakers complete this monochromatic look with a sporty twist. I always recommend trying bold colors with oversized shirts – they can really make an impact!
17. Denim on Denim and White Sneakers
Take the Canadian tuxedo to new heights with a light blue denim shirt dress layered over wide-leg jeans in a matching wash. A brown crossbody bag and white sneakers keep the look grounded. This outfit is perfect for those days when you want to be comfortable but still look like you made an effort.
18. White Button-Up and Vest
For a cozy yet stylish look, layer a cream sweater vest over an oversized white button-down shirt. Pair with a beige fedora, glasses, and a small brown patterned crossbody bag. White ankle boots add a modern touch to this neutral ensemble. This is one of those trendy oversized button up shirt outfits that’s perfect for transitional weather.
19. White Button-Up Shirt and Cozy Sweater
For the ultimate in comfort, pair an oversized white button-down shirt with an oversized cream cable knit sweater and cream shorts. White socks and black chunky shoes add a trendy finish to this cozy look. I recommend this outfit for lazy weekends or casual hangouts with friends.
20. Pink Shirt and White Jeans
Last but not least, make a statement with a bright pink oversized button-down shirt paired with high-waisted white jeans. Large sunglasses and vibrant pink heels complete this bold, eye-catching look. This outfit is perfect for those days when you want to stand out and make a lasting impression.
And there you have it – 20 chic ways to style an oversized shirt! From casual cool to street style glam, these outfit ideas prove just how versatile this wardrobe staple can be. Remember, the key to rocking an oversized shirt is all about balance. Pair it with fitted bottoms, add accessories to define your waist, or play with layers to create interesting silhouettes.
So, which of these oversized shirt outfit ideas will you try first? Whether you’re going for a casual oversized white shirt outfit or a trendy oversized button up shirt outfit, there’s something here for everyone. Keep these styling tips in mind, and you’ll be rocking the oversized shirt trend like a pro in no time. Happy styling!