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A Modern Must-Have: How To Style an Oversized Button-Up Shirt

A Modern Must-Have: How To Style an Oversized Button-Up Shirt The button-up shirt has long been an everyday fashion must-have. It's t-shirt's significantly more formal cousin, appropriate for everything from...

A Modern Must-Have: How To Style an Oversized Button-Up Shirt

The button-up shirt has long been an everyday fashion must-have. It's t-shirt's significantly more formal cousin, appropriate for everything from a board meeting to being a witness at your childhood friend's courthouse elopement at the very last minute.

The oversized trend has introduced a new way to wear this century-old basic. In oversized form, the button-up transforms from a practical businesslike garment to a bastion of understated cool. Here's how to style an oversized button-up, bringing a sense of effortless luxury to your wardrobe.

Approaching How To Style an Oversized Button-Up

Once you experience the drapey, lightweight, but structured energy of the oversized button-up, you'll probably want to slot it into every outfit in your closet. Not only does the oversized cut add interest to a typical business casual silhouette, but it also communicates a slight lack of formality appropriate for many modern office spaces.

That said, there are many other ways to style this piece that make it even more versatile than the standard button-up. It slots perfectly into casual looks, too, from a weekend brunch to a relaxed stroll through an art gallery.

An oversized button-up can also become your secret weapon for those tricky dress codes that, infuriatingly, don't actually mean anything.  You know the ones: "Upscale, yet casual," "Slightly dressy" or "Rustic semi-formal." An oversized button-up is a solid nod to formality that never comes across as overdressed.

Oversized Button-Up Basics

Before jumping into styling ideas, it might help to clear up general misconceptions about the oversized trend.

Balance Isn't Strictly Necessary

Contrasting silhouettes can bring a lot of interest to an outfit that otherwise might blend into the crowd. Adding one oversized piece and keeping other elements in a standard size is one easy way to introduce such a contrast. Don't feel bound by this as a "rule," however. An all-oversized look has its own charm and is sure to make a big statement.

The Right Amount of Oversized Can Vary

Proportions for oversized looks will vary based on your individual body. Oversized clothing can be too big to be comfortable, but it can also be not quite oversized enough. The good news is, that window is pretty generous. Look for an oversized button-up that feels relaxed and loose on you but isn't quite big enough to get caught in a door.

Oversized Can Work for Petites, Too

If you're a petite woman, you may have a latent, deep-seated fear of being "swallowed up" by your clothes. This may even manifest as a recurring nightmare about a houndstooth jacket whose name becomes very literal, all of a sudden (speaking from experience.)

If you have a smaller frame, you don't need to back away from the oversized trend slowly with a seam ripper in hand. You just need to style creatively within your personal silhouette comfort zone.

Maybe that means wearing oversized everything and living your Billie Eilish best life. It could also mean going with a cropped pair of oversized jeans or shorts instead of full-length ones. On the conservative end, you can stick to one oversized item per outfit that's roomy instead of absolutely massive.

6 Ideas for How To Style an Oversized Button-Up

Here are a few jumping-off points for your oversized button-up looks. Pairing this versatile wardrobe piece with different pants and skirts can completely transform its vibe.

1. Pencil Skirt

A typical button-up shirt with a pencil skirt feels professional, but it can also skew slightly dated. Update this business casual look by reaching for an oversized button-up instead. The tight fit of the pencil skirt provides balance and contrast while giving the overall outfit a well-defined shape. A vegan leather pencil skirt can add even more subtle edge.

2. Oversized Jeans

Button-up shirts aren't just for weekdays. Paired with similarly oversized jeans, the button-up becomes a stylish choice for casual occasions on the weekend. This look is a lifesaver during hot summer months, as a blousy cotton shirt with a relaxed fit keeps you cool and collected even when outside.

3. Oversized Blazer

An oversized shirt and blazer combination is all the rage on the world's runways. Stars like Hailey Bieber are taking this avant-garde look into daywear, as well. Double up on oversized formals by pairing your oversized button-up with a large suit jacket. Make sure the sleeves on the jacket cover part of your hand, but not the majority of it for the right oversized fit.

4. Two-Tone Pants

Since an oversized button-up is usually fairly neutral in its texture and color, add these two elements elsewhere in the outfit with contrast tone pants. This way, you'll have an interesting fashion choice on both the top and bottom of the look for excellent balance.

5. Metallic Skirt

Set the clean and professional lines of an oversized button-up against a metallic sequin skirt for a well-balanced and fashion-forward outfit. To dress up the look, try it with heels or metallic flats while matching plenty of jewelry to the tone of the sequins. You can also dress down a shiny skirt and oversized button-up with more casual shoes and thin, minimalist jewelry.

6. As a Dress

One undeniably sexy styling option for the oversized button-up is wearing it as a minimalist shirt dress. Model and actress Emily Ratajkowski coordinated her belt, shoes, bag and sunglasses to a warm brown theme to keep her shirtdress outfit chic and neutral. This understated styling choice draws even more attention to the daringly short cut and the subversive element of using a menswear piece to look ultra-femme.

Learn How To Style an Oversized Button-Up With More Cutting-Edge Fashion

Embrace the modern, blousey button-up to unlock a new world of possibilities for your wardrobe. Learning how to style an oversized button-up can make any office look more interesting. You'll also reach for it for weekend and casual looks. At Kate Hewko, we believe that having fun and taking risks with your personal style is possible for anyone and everyone. Browse our collection to find the latest runway styles at affordable prices.

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