How to Style Oversized Button-ups: The Queen of Basics
Call Tom Cruise’s character from Risky Business, because we urgently need to borrow his legendary shirt. Let’s be honest, his look is best suited for Halloween and solo dance parties in the living room. Fortunately, we’ve figured out how to style oversized shirts so that they become the most important items in our wardrobe.
There are a few items every woman should own, and a classic collared shirt is one of them. Whether you prefer a sheer, coastal-grandmother-style shirt or a preppy, elegant version, they come in many different shapes. Today we’re talking about the versatility of an oversized style. You should choose a shirt that is larger than your usual size, but not too loose-fitting, so that the look really comes into its own. As a rule, choosing one or two sizes larger is sufficient.
When it comes to color, solid blue or bright white shirts are a good choice. They can be combined in many ways and are real all-rounders in your wardrobe. If you want to play around with your outfits a little, opt for an unexpected color or a multicolored striped pattern. Ultimately, it’s less about the color and print and more about the fit. Do you have the perfect garment in mind but aren’t sure how to style oversized shirts to suit your personal style? Then you’ve come to the right place.

How to Style Oversized Button-Ups: 3 Easy Ways
The way we wear shirts is evolving. They used to be simply an integral part of business attire, best suited for the office. Choosing larger sizes opens up new styling possibilities that we love. The answer to the question of how to style oversized shirts is not so simple. Don’t worry, ladies, that’s a good thing. It means there are countless ways to rock a shirt, no matter the occasion. We’ve compiled our three best techniques below to help you get started.
Good to know: The terms “button-up” and “button-down” are often used interchangeably, but there is a distinct difference between the two. A button-up is a shirt that literally buttons up the front—hence the name. Button-down shirts, however, are button-ups with additional buttons on the collar. These shirts often lend a more polished and professional look.
1. Wear It Unbuttoned as an Alternative Layer
An easy solution for styling oversized shirts is to brush them against the grain and wear them unbuttoned. Put away your light cardigans and jackets and opt for this alternative layer instead. Looking for an athleisure outfit that will take you from brunch to a game of bocce with the family? Wear a cotton blouse paired with a tennis dress and white sneakers. The casual fabric of the blouse makes this outfit sporty yet stylish and suitable for activities off the tennis court. To emphasize the sporty look, pair it with a belt bag, but make it interesting. Don’t wear it around your waist; instead, strap it diagonally across your chest. This will keep your hands free and still look fashionable.
2. Tie It Up for a Go-to Summer Style
Our next technique for styling an oversized shirt is to tie it at the front. There are two ways to do this. First, leave it unbuttoned, take the two ends of the shirt, and tie them together. This shortens the shirt and works well as a subtle option over a swimsuit. Fancy a day at the beach? For a flirty twist, tie it loosely and let the shirt fall off one shoulder. Or button up the top half of the buttons and then tie the two ends together with the remaining fabric. Pair your shirt with high-waisted shorts and sandals for a wearable outfit that’s perfect for fun in the sun.
3. Go for the Half-tucked Method for Extra Fashionista Points
When it comes to tucking shirts into pants, you’ve probably heard of the French tuck method. This involves tucking only the front of a blouse into the pants, while the back hangs out. The half-tuck method is slightly different and one of our favorites when it comes to styling oversized shirts. This technique is similar to what it sounds like and creates a deliberately tousled look. To achieve this look, leave the last three or four buttons undone. Then tuck only one side into your pants, leaving the other side hanging out. To be honest, this style may not be for everyone, especially if you prefer a neat college look. However, if you want to breathe new life into your outfits, we recommend giving it a try.
How to Style an Oversized Button-up With Jeans

Whether tucked in or untucked, knotted or unknotted, buttoned up or buttoned down—you can’t go wrong when deciding how to style an oversized shirt with jeans. These two pieces are a natural pairing and look great with little effort. If you want to elevate your jeans and shirt combo, we have a few ideas for you. In case you haven’t heard, Americana fashion is back, and jeans are at the center of the trend—especially denim on denim. Try the good old Canadian tuxedo with your favorite mid-wash jeans and an oversized chambray shirt.
Alternatively, you can take inspiration from the color wheel to see which colors go well together. Pink and orange look fantastic with blue, so try one of these colors. Pair a fuchsia striped shirt with a tangerine handbag or headband for a colorful look.
How to Style an Oversized White Button-Up
Creating an outfit around a classic crisp white shirt is probably one of the easiest pieces of clothing to style. If you’re ever asked how to style an oversized white button-down shirt, you’ll know what to say. Any of the methods above will work—it’s that simple. If you’re looking for specific styling tips, why not try the dark academia style? Are you going back to school or spending all your free time at the local library? In either case, this academic style is just right for you.
Combine the crisp white look of the shirt with moody fall colors such as black, gray, brown, and burgundy. Wear it with a plaid skirt and a knit vest over it so that the hem of the shirt peeks out from underneath. Slip on a pair of black patent loafers and complete the outfit with a crossbody bag. Finally, top off your look with a trench coat as the finishing touch.
Now that you feel more confident about how to style oversized shirts, are you ready to give it a try? Let our style experts do the work for you. Take our style quiz, order a Fix, and sit back and relax.