How to Style Oversized Button-ups: The Queen of Basics

Call up Tom Cruise’s character from “Risky Business” because we need to borrow his iconic button-up shirt, ASAP. Let’s be honest, his look is best reserved for Halloween and solo living room dance parties. Luckily, we’ve figured out how to style oversized button-ups in order to turn them into prime players in our closets. 

There are a few clothing items that every woman should own, and a classic collared shirt is one of them. Whether you prefer a gauzy coastal grandmother style shirt or a preppy, polished version, they come in many different forms. Today we’re talking about the versatility of an oversized style. You’ll want a shirt that is larger than your usual size, but not overly baggy to properly pull off the look. Typically, sizing up one or two times will do the trick. 

In regard to color, a solid blue or crisp white shirt comes in clutch. They’ll add the most miles to your styles and prove to be a true wardrobe workhorse. If you want to have a little fun with your outfits, opt for an unexpected color or multi-colored striped pattern. Ultimately, it’s less about the color and print, and more about the fit. Do you have the perfect piece in mind, but you’re not sure how to style oversized button-ups to suit your personal aesthetic? Well, look no further because you’ve come to the right place. 

How to Style Oversized Button-Ups: 3 Easy Ways

The ways in which we wear button-ups are evolving. In the past, they were simply a business attire staple that was best suited for the office. Sizing them up opens the door for new style possibilities, and they’re calling our name. The answer to how to style oversized button-ups is not so straightforward. Don’t worry, ladies, that’s a good thing. It means that there are countless ways to rock a button-up no matter the occasion. We’ve gathered our top three techniques below to get you started. 

Fun Fact: The terms “button-up” and “button-down” are often used synonymously but there is a distinct difference between the two. Any button-up is a shirt that literally buttons up in the front—hence the name. However, button-down shirts are button-ups with extra buttons on the collar. These shirts often give a more tailored and professional appearance.

1. Wear It Unbuttoned as an Alternative Layer

A no-fuss solution for how to style oversized button-ups is to go against the grain by wearing them unbuttoned. Tuck away your lightweight cardigans and jackets and opt for this alternative layer instead. Looking for an athleisure outfit that will take you from brunch to bocce ball with the family? Wear a cotton button-up coupled with a tennis dress and white trainers. The casual shirt material will make this workout-ready outfit stylish and appropriate for off-the-court activities. To lean into the sporty vibes, accessorize with a belt bag, but make it interesting. Instead of wearing it around your waist, buckle it diagonally across your chest. It remains hands-free but with a fashion-forward feel. 

2. Tie It Up for a Go-to Summer Style

Our next technique for how to style an oversized button-up is to wear it tied in the front. You can do this in two different ways. Firstly, leave it unbuttoned, gather the two tails of the shirt and tie them together. By doing so, this will crop the shirt, making it a lowkey option for wearing over a swimsuit. Beach day, anyone? For a flirty twist, tie it loosely and let the shirt fall off of one shoulder. Or secondly, button the first half of the buttons and then tie the two tails with the remaining fabric. Style your shirt with high-waisted shorts and sandals for a wearable outfit that’s suited for some fun in the sun. 

3. Go for the Half-tucked Method for Extra Fashionista Points

When it comes to tucking shirts, you’ve probably heard of the French tuck method. This involves twisting and tucking just the front of a blouse into pants and leaving the back untucked. The half-tuck method is a little different, and one of our favorites when choosing how to style oversized button-ups. This technique is similar to how it sounds and provides a deliberately disheveled look. To pull it off, leave the last three or four buttons undone. Then, tuck only one side while leaving the other side hanging out. Truth be told, this style may not be for everyone. Especially if you prefer a neat collegiate fashion ensemble. However, if you’re looking to breathe new life into your outfits, we encourage you to give it a try. 

How to Style an Oversized Button-up With Jeans

Tucked or untucked, tied or untied, buttoned or unbuttoned—you can’t go wrong when deciding how to style an oversized button-up with jeans. These two closet essentials are a natural pairing and will look great with little effort. If you want to elevate your jeans and shirt combo, we’ve got a couple of ideas. If you haven’t heard, Americana fashion is back, and jeans are at the center of the trend—especially denim on denim. Give the ol’ Canadian tuxedo a go with your favorite medium-wash blue jeans and an oversized chambray shirt.  

As an alternative, turn to the color wheel for inspiration on which colors go well together. Pink and orange look stellar with blue, so give either shade a whirl. Match a fuchsia striped button-up with a tangerine handbag or headband for some colorful coordination.

How to Style an Oversized White Button-Up 

Creating an outfit around a quintessential, crisp white shirt is arguably one of the easiest pieces to style. If someone ever asks you how to style an oversized white button-up, you’ll know what to tell them. Any of the above methods will work—it’s as simple as that. If you’re looking for specific styling advice, give dark academia a try. Are you heading back to school or finding yourself spending all of your free time in the local library? Either way, this scholarly aesthetic is right up your alley. 

Contrast the clean white look of the shirt with moody fall colors like black, grey, brown and burgundy. Couple it with a plaid skirt and layer a sweater vest over top, leaving the shirt tails peeking out the bottom. Pop on a pair of black patent loafers and accessorize with a crossbody satchel. Lastly, top off your look with a trench coat as a cherry on top of the outfit.

Are you feeling more confident about how to style oversized button-ups and ready to give them a try? Let our style experts do the heavy lifting for you. Take your style quiz, order a Fix and sit back and relax. Five styles will arrive on your doorstep allowing you to try them before you buy. Keep what you love and send back the rest. In the meantime, head over to Stitch Fix Freestyle™ to find items selected for your style and size. Shipping and returns are free.