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how to wear oversized button down shirt

How To Wear Oversized Button-Down Shirts: 10 Effortless Looks 

We’ve been binge-watching OG Gossip Girl (our staple show of the Summer… anyone else?) and we realized that miss Serena van der Woodsen reallly knew what she was doing with the oversized button downs. Looking to style one yourself? Here’s the tea!

Oversized button-ups are chic, versatile, and casual in the HOTTEST way. Today, we have a TON of tips and tricks on how you can style an oversized button down! And don’t you worry, you don’t have to be an Upper Eastside princess to rock it just as well. 😉 So let’s get into it, shall we? Here’s exactly how to wear oversized button-up shirts! 

10 Must-Try Oversized Button-Down Shirt Outfits

While oversized button down outfits ARE super versatile, there are def things you need to consider when styling them. Like first off, are we making it the WHOLE look? Are weee styling it on top of a dress? Using the “big shirt little pants” method that we all know and love? Going casual and comfy? 

Oversized button-down shirts come in a ton of diff fabrics, colors, and styles. Believe it or not, there IS indeed a method to the madness. Which is why we took the stress off of you having to figure it all out yourself! Isn’t that what we’re here for??? Let’s get into it!

How To Wear Oversized Button-Down Shirts: 10 Effortless Looks 

How To Wear Oversized Button-Down Shirts: Fun And Flirty Fashion

Big Shirt Little Pants

Right off the bat, we’re hitting the infamous big shirt little pants method. We’re thinking: night out with the girls. Wearing a chic little a-line mini skort paired with the most fashionable oversized white button-down would have you the talk of the TOWN. This shirt has a single spade pocket, pleated cuffs, and tends to hit just below the hip (depending on height, of course).

Our favorite thing about this outfit is its laid-back sexiness. You can wear your hair in a messy bun, sleek and styled back, in a high pony, rings, hoops, studs, necklace or no necklace… but honestly, are there any rules to “going out” accessories when you wear an outfit like THIS?! 

Over A Dress

Okay babe, we’re about to call you out… with love. We KNOW that you have “what to wear over a dress” ALLL throughout your search history. No shame in that, we’ve all been there! But look no further, we’ve got you!! The answer? An oversized button-down, duuhhh! 

If you’re looking for something to throw over a sundress like this black midi-dress or this black mini-dress  to make it more casual, this Pru oversized button down is on the other line. 📞 It’s American-made, 100% Organic Turkish cotton, and the best part??? It’s UPF 45-50+ which means it’s gonna block about 98% of the sun’s rays. Truly the best of both worlds. 

As A Dress

Instead of wearing an oversized button-down OVER your dress, what if you wore it AS your dress??? Don’t let this intimidate you! It’s chic, it’s sexy, it’s EVERYTHINGGG. Let us paint you a picture. 

This oversized cotton shirt dress is the PERFECT start to this look. Because the button-down is white, you could pair it with a number of colorful shoes and accessories to spice up the look. For example, these pink square toed heels are the perfect add-ons, creating a look to DIE for. 

Add A Corset

Oh just wait, we aren’t off this “wearing an oversized button up as a dress” train just yet. (And not to be biased, but this may be our favorite way to style an oversized button up shirt YET). Whether you’re going out for a meeting, having lunch with your girls, or you’re just looking for an outfit for a night out, this covers it ALL. 

This American-made, slouchy cotton button down is the perfect length and material to wear as a dress. It’s collard, has half sleeves, and… wait for it… it has SIDE POCKETSSSS. Sorry Cyndi Lauper, girls just wanna have side pockets, actually. Pairing this with a genuine leather handcrafted corset top (that comes in EIGHT diff colors, might we add) makes this look super sexy and super versatile. 

Over A Onesie 

Okay okay, we’re done with the dress outfits now. We don’t know about you girls, but we are huuuuge fans of onesies at the moment. Not only can you dress them up or down, can we like, talk about how comfy they are???

This onesie is designed to be close fitting but stretchy, with a scoop-neck and a hemp stretch blend. And because this onesie is solid-colored, we envision it paired with a super colorful piece like THIS Parker button down. It’s made of 55% linen with short sleeves and an oversized fit, so it’s truly the perfect staple outfit for the summer. 

As A Cover-Up

Speaking of summer, did someone say they were looking for a stylish cover-up?!? We’re mind readers at this point. This linen boyfriend shirt was MADE for beach or pool wear. It has shell buttons, an oversized fit, and is made from linen so it’s super breathable. 

The best part about it is the vibey pattern it has made into the shirt. It just looks like THE perfect cover up! 

Paired With Jeans

Oversized button-downs are GREAT to pair with some high waisted jeans. Especially if you wanna dress an outfit up ever so slightly? We can’t think of anything better than this Elise Oversized Button-up. It’s 100% cotton, features front and cuff buttons, and has a front pocket. 

PLUS, you get your money’s worth with this piece! It’s great to layer on allll year long. Wear it tucked into your favorite pair of American-made jeans with the sleeves rolled up in the summer to cool down, OR wear untucked during the winter with the sleeves down to keep your warmth. 

How To Wear Oversized Button-Down Shirts

Short Matching Set

Who DOESN’T love a matching set??? If you’ve read some of our other blog posts, you know we’re matching sets #1 supporter. Check out this super chic oversized 2 piece set

It’s made of breathable material and stretchy spandex, so you’ll look just as relaxed as you feel. PLUS, we love a color contrast look. Can’t go wrong packing this into your suitcase for your next relaxing beach vacay! 

Long Matching Set

You didn’t think we just meant a short sleeve and shorts combo matching set, right??? Oh noooo girlfriend, we love them ALL. And dare we say… we’re trying to bring the big shirt big pant trend back??? It sounds CRAZY, but just check it out. 

This Miley Set features a white shirt that’s designed to be an oversized long sleeved collared blouse, paired with this SOFTEST looking baggy (but chic) pants. And who said your shoes couldn’t be just as comfortable as the rest of your outfit?? Add on these lightweight leather sandals and you’re ready to go! 

Oversized Sleep Set

We don’t just find dressed up looks for you girls, we loovveee to plan for a night in. We’ve given you some ways to dress up an oversized button-down, so let’s talk dressing down–but in the best way. If you wanna spend a night in binge-watching Gossip Girl (we’re just megafans, okay?!), making martinis and living out your true Serena van der Woodsen dreams, you HAVE to play the part. 

This button-up set is what dreams are made of. It comes as a matching set, is luxe satin made of 100% polyester, and is the BEST way to get some much needed R&R. Coming in 11 different colorways, you can match it with your slippers ( we love these and these from Etsy! ), your scrunchies, your facemasks… okay you get it. SO stylish, but so comfy. 

sleek and chic button down shirt

What way will YOU style your oversized button-down look? 

We’ve brought you SEVERAL different chic, fashionable, and creative ways to style an oversized button-down. We are bringing casual sexiness BACK, baby! 

With that being said… we wanna know which look was your favorite! Which look will YOU be rocking this year?! I mean honestly, we think you’d kill it in every one.

Don’t forget to check out our blog and shop for all of the HOTTEST American-made outfits, picked and styled just for you. 😉

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