I stole my first oversized shirt from my husband about six years ago and I have absolutely no plans to give it back. It was a soft white button-down that had gone a little floppy in all the right places, and one lazy Saturday I threw it on over some jeans and felt instantly put together.
My sister keeps asking me how I always look “kind of dressed” without trying and honestly the answer is almost always the same shirt in a different combination.
So I made her this list, and now I’m making it for you too.
20 Ways To Wear A Big Shirt And Still Look Like You Meant It
Oversized Button-Down With Relaxed Jeans
This is the combo I keep coming back to again and again. A slouchy shirt with relaxed jeans is the definition of a lazy-but-cute Sunday, and it never lets me down.
Tuck just the front hem into the waistband, leave the back loose, and roll the sleeves up to the elbow. That tiny bit of tucking is what keeps the oversized button down outfit from swallowing you whole.
Button-Down Shirt With Denim Shorts And Sneakers
For running errands or a coffee walk, this one is my go-to. A crisp button up shirt outfit paired with denim shorts and clean white sneakers feels breezy and easy.
I like to leave a couple of buttons open at the top and knot the very bottom hem so it doesn’t look like I forgot my pants. So simple. So good.
Long Denim Shirt Dress With Loafers
A denim shirt dress that hits mid-thigh with a pair of brown loafers is one of those looks that pretends it took effort. It did not.
Belt it or don’t. On the days I feel like defining a waist I add a thin belt, and on the days I don’t, I just let it hang and call it done.
Relaxed Button-Down With Denim Shorts
Yes, this looks a little like the earlier shorts one, and that’s on purpose because I wear it slightly differently every single time. Here I go for a more relaxed, unstructured shirt in a soft chambray instead of a crisp cotton.
It’s a little more slouchy, a little more weekend. Bare legs, flat sandals, sunglasses pushed up in my hair. In fact this is what I wore to a farmers’ market last month and my friend Dana asked where I got the shirt.
Black Skinny Jeans With Oversized Shirt
Skinny jeans get a bad rap these days but paired with a big, loose top they balance out beautifully. The volume up top and the slim leg down below is a formula that just WORKS.
Black skinnies with a big white shirt is about as classic as it gets, and it’s one of those oversized shirt outfit women reach for when they want to look tall and lean without thinking too hard about it. Add ballet flats or ankle boots depending on the season.
Oversized Shirt With Boxer Shorts
I will not lie to you, I was skeptical about the boxer short trend. It felt like I’d forgotten to get fully dressed. But then I tried it and now I get it.
A big shirt half-tucked into a pair of soft cotton boxer-style shorts is the comfiest thing on earth for a warm afternoon at home, and it looks intentional enough to answer the door in. Slides on the feet, done.
Tie Belt With Oversized Shirt And Shorts
So here’s a small trick that changes everything. Take that same big shirt and shorts and wrap a fabric tie belt around the middle of the shirt.
Suddenly there’s a waist where there wasn’t one, and the shirt blouses out a little over the belt in a way that looks almost designed. It’s my favorite five-second upgrade.
Dior Sneakers With White Shirt Dress
Okay, the Dior sneakers are aspirational, I know. But the point stands with any pair of clean, slightly elevated white sneakers you already love.
A white shirt dress with a fresh sneaker is the outfit I pack when I’m traveling and want ONE thing that covers a whole day, from a museum in the morning to a nicer dinner at night. It photographs well too, if that matters to you (it matters to me).
Denim Shirt Dress With Statement Belt
Same denim shirt dress idea from before, but this time the belt does the talking. A wide leather belt with a bold buckle takes a plain denim dress and gives it a little bit of attitude.
I cinch it right at the natural waist and let the skirt part flare out below. It’s amazing what a good belt can do for a piece you were about to donate.
Denim Shirt Dress Over Straight Jeans
This is a layering move I picked up years ago and never stopped doing. Wear the denim shirt dress open, like a long shirt-jacket, over a plain tee and straight jeans.
Double denim scares people but it really shouldn’t. Just keep the two washes a little different from each other and you’re golden. It’s cozy for those in-between fall days when it’s cool in the morning and warm by noon.
White Button-Down With Straight-Leg Jeans
The white shirt and straight-leg jeans combo is the outfit I trust when I have no idea what the day holds. Meetings, lunch, a school pickup, all of it.
It’s the most grown-up version of the boyfriend shirt outfit, the one that looks polished enough that no one questions whether you planned it. Roll the sleeves, add gold hoops, and you’re ready for basically anything.
White Shirt Dress With Gold Chain Belt
A gold chain belt is one of those accessories I forget I own and then rediscover with great joy. Slung low over a white shirt dress it adds just enough shine to feel a little dressed up.
I wore this to my niece’s birthday lunch and my mother-in-law told me I looked “very put together,” which from her is a rare and precious compliment. I did not tell her the dress was on sale.
Pink Button-Down Shirt With Black Shorts
Color! A soft pink button-down brings a little warmth to your face and looks so pretty against plain black shorts. It’s a nice break from all the white and denim.
Pale pink is one of those shades that flatters almost everyone, and it keeps a summer outfit from feeling too plain. Flat sandals and a straw bag finish it off.
Button-Down Shirt With Denim Midi Skirt
A midi denim skirt with a big shirt tucked in is such a nice, easy silhouette for those days when shorts feel like too much and pants feel like too much and you just want a middle option.
I tuck the shirt in all the way around for this one, since the skirt already has structure. A little leg peeks out below the knee and it feels breezy and just the right amount of covered.
Lululemon Shorts With Striped Button-Down
This is my dropping-the-kids-off-and-then-maybe-a-walk outfit, and I’m not even a little bit sorry about it. Athletic shorts under a slouchy striped shirt is the sneakiest way to look casually cute while wearing what are essentially comfy clothes.
The striped shirt does all the work here. It makes the athletic shorts read as “an outfit” and not “I gave up.” Sneakers, sunglasses, and a big drink to go.
Dark Wash Jeans With White Button-Down
Dark wash jeans just look a little dressier than light ones, and with a crisp white shirt they can carry you into a nice dinner without a second thought. That contrast of dark and light is so clean.
This is basically the uniform I default to for date night with my husband when I can’t decide on anything else. Heeled mules, small earrings, done in five minutes.
Striped Button-Down Shirt With White Jeans
Stripes and white jeans give me all the coastal, breezy, pretending-I’m-on-vacation feelings. It’s crisp and fresh and looks great with a little sun on your skin.
I keep the striped shirt loose and half-tucked and roll the sleeves, and I let the white jeans do the summery lifting. Espadrilles or flat sandals both work beautifully here.
Oversized Blue Striped Shirt With Denim Shorts
A big blue and white striped shirt with denim shorts is one of those effortlessly relaxed looks that never seems to go out of style, and it’s the perfect boyfriend-style outfit for a lazy beach day.
Grab it slightly too big, knot the front, throw it over a swimsuit, and wander down to the water. This is the oversized button up outfit I live in when we’re near the ocean and I refuse to overthink anything.
White Shirt With Navy Bermuda Shorts
Bermuda shorts came back and I, for one, am thrilled about it. A tailored navy pair with a crisp white shirt tucked in feels smart and a little bit preppy in the best way.
It’s the outfit I’d wear to a summer lunch out or a casual daytime event where I want to look nice but still be comfortable. Loafers or flat sandals, a small bag, and I feel great.
White Oversized Shirt With Black Flared Pants
And to close things out, a slightly more elevated evening idea. A big white shirt with black flared pants is chic and long and a little dramatic in a way I really love.
Tuck the shirt in loosely so the flares can do their swooshy thing, and add a heel to lengthen the whole line. This is the one I save for the nights I actually want to make an effort, and it always makes me feel a little bit taller and a little bit more myself.
