Look, oversized shirts have basically become that one piece you gotta have in your closet – they’re comfy as hell, go with literally everything, and honestly make you look like you’ve got your life together even when you definitely don’t.
So if you’re sitting there wondering how to actually style these bad boys, well, you’re gonna love what’s coming. We’ve got everything from super chill weekend vibes to looks that are a bit more polished.
These oversized shirt outfit ideas are gonna show you exactly how to rock this trend without looking like you’re drowning in fabric.
Just keep scrolling and check out these 19 awesome ways to style your oversized shirts – you’re gonna look amazing without even breaking a sweat!
1. White Oversized Shirt and Dark Wash Jeans
Let’s kick things off with a combo that literally never fails. Grab a crisp white oversized button-up and throw it on with some dark wash wide-leg jeans. Add some pointed-toe heels and boom – you’re done.
2. White Button-Down and Brown Wide-Leg Pants
This one’s giving me all the expensive vibes, you know what I mean? Take your white oversized button-down and pair it with some brown wide-leg pants. The color combo is just chef’s kiss.
3. Blue Striped Shirt and Black Wide-Leg Pants
Okay, this outfit’s perfect for when you gotta look professional but you don’t wanna look like you’re trying too hard. We’re talking light blue striped oversized shirt with black wide-leg pants. The stripes against the solid black? It’s such a nice contrast.
This is your go-to when you need to impress at work but still wanna be comfortable enough to grab drinks after.
4. Pale Yellow Shirt and Light Wash Jeans
This look is so soft and pretty, I can’t even. Grab a pale yellow oversized button-up, throw on some light wash wide-leg jeans, and finish with white pointed-toe shoes.
The pastel yellow is perfect for spring and summer – it’s like wearing sunshine, but in a good way, not in a “why are you so cheerful on a Monday” way. Those white shoes just tie everything together beautifully.
5. White Shirt and Black Fringe Mini Skirt
Now we’re getting fancy! This combo’s definitely for when you wanna turn some heads. White oversized button-down meets black fringe mini skirt and black peep-toe heels. The fringe adds this fun, flirty movement that’s just so good.
Pro tip: tuck that shirt in and maybe leave a couple buttons undone at the top. You’re going for “effortlessly sexy,” not “trying too hard.”
6. Blue Striped Shirt with Denim Shorts
This is basically summer in an outfit. Layer a blue striped oversized shirt over a white top (leave it unbuttoned – we’re using it as a jacket here), add some light wash denim shorts and white sneakers.
It’s giving me major beach vibes, like you just came from brunch by the ocean even if you’re nowhere near water.
7. Black Oversized Shirt Dress
Sometimes you just gotta keep it simple, right? This black oversized shirt dress with puffy sleeves is everything. Throw on some slide sandals and you’re good to go. Perfect for running errands or meeting friends for a casual lunch.
8. White Shirt Layered Over Black
Here’s a sporty-casual look that’s so easy it hurts. White oversized button-up left open over a black fitted top, black leggings, and white sneakers.
This layering situation is perfect for when the weather can’t make up its mind. Plus, black and white? Can’t go wrong. You’ll look put-together even if you assembled this outfit in the dark.
9. Denim Shirt Jacket and White Lace Pants
This outfit’s giving me serious boho vibes and I’m living for it. Oversized denim shirt jacket meets white lace wide-leg pants and black slides.
The casual denim with the fancy lace? It’s like mixing your favorite comfort food with a gourmet meal – unexpected but so good. Perfect for summer festivals or that outdoor brunch spot everyone’s been raving about.
10. Matching Shirt and Shorts Set
Y’all, matching sets are a game-changer. Oversized button-up with matching shorts and some strappy sport sandals. You literally don’t have to think about what goes together ’cause it’s already done for you.
Plus, everyone’s gonna think you’re super put-together when really you just grabbed two pieces that came together. Work smarter, not harder, am I right?
11. Red Short-Sleeved Shirt and Black Pants
Wanna make people notice you? This red short-sleeved button-up with black wide-leg pants will definitely do the trick. The red’s bold enough to turn heads but the black pants keep it from being too much.
This works for pretty much everything – day, night, that weird in-between time when you’re not sure what the vibe’s gonna be.
12. Mint Green Shirt Over White Dress
Okay, this styling trick is genius. Take a mint green oversized button-up and wear it over a white mini dress. Leave it unbuttoned and tie it at the waist. It’s like getting two outfits in one!
The mint green is so fresh and summery, it’ll make you look like you actually enjoy hot weather even if you’re secretly counting down to fall.
13. Yellow Striped Shirt and White Lace Shorts
This outfit is basically happiness in clothing form. Yellow striped button-up plus white lace shorts equals instant sunshine vibes. The stripes keep it casual while the lace adds that sweet, feminine touch.
You’re gonna look like you’re on vacation even if you’re just going to the grocery store.
14. Rust-Colored Shirt and White Wide-Leg Pants
For all my earth-tone lovers out there, this one’s for you. Rust-colored oversized button-up with white wide-leg pants is such a sophisticated combo.
It’s perfect for when summer’s ending but fall hasn’t quite started yet. You’ll look expensive and put-together without trying too hard.
15. White Shirt with Cami and Denim Shorts
Another killer layering option coming at ya! White oversized button-up worn open over a black cami, light wash denim shorts, and white sneakers. It’s effortless summer style at its finest.
The black cami underneath adds this nice contrast that makes the whole thing pop. This is your “I woke up like this” outfit that actually took two seconds to put together.
16. White Shirt and Black Wide-Leg Pants
Sometimes you just gotta embrace the basics. White oversized button-up, black wide-leg pants, and ballet flats. Simple? Yes. Boring? Hell no. The ballet flats add this delicate, feminine touch that elevates the whole thing.
This is perfect for work or when you need to look polished but you’re running on three hours of sleep.
17. Blue Striped Shirt and White Trousers
Getting major “I summer in the Hamptons” vibes from this one (even if you’ve never been there). Blue striped oversized button-up with white wide-leg trousers is so crisp and fresh.
You’re gonna look like you own a yacht even if you get seasick on a paddleboat.
18. Blue Striped Shirt and Baggy Jeans
For when you wanna look cool without trying, this is it. Blue striped oversized button-up meets light wash baggy jeans. Yeah, we’re doing double relaxed fits and it totally works.
This is that “I just threw this on” look that actually looks incredibly stylish. It’s giving off-duty model vibes.
19. Light Blue Shirt and Black Maxi Skirt
Last one and it’s a good one! Light blue striped oversized shirt with a black maxi skirt. This combo shouldn’t work but it totally does. You’ve got casual meeting dressy in the best way possible.
It’s comfy enough for all-day wear but chic enough for that dinner thing you forgot about. This outfit’s gonna save your butt more times than you can count.
