6 Oversize Button-Down Shirt Outfits That Are Polished Yet Chill

What could be better?

Re Ona
a model wearing a white oversize button-down shirt with jeans

When it comes to getting dressed, simplicity invariably wins. Standing out in a fun trend or cleverly devised ensemble always feels like a sartorial pat on the back. But most days, what’s better than an easy-to-toss-on — yet still elevated — look, like oversize button-down shirt outfits?

While designers continue to deliver on modern shirting with splices, flourishes, and asymmetry each season, there’s a current interest in the most classic renditions (where not much has changed within the garment’s structure). Thanks to its inherent air of refinement, the white button-down shirt in all iterations (striped, colorful, printed) feels infused with a cool factor lately.

The au courant key? Opting for an ultra-roomy fit and nostalgic styling choices hitting on all the aesthetics of the moment from tennis to country club and, most recently, golf (yes, really). They’re the perfect pairing with leggings, baggy jeans, or miniskirt — even coordinating bottoms as a leisurely yet sophisticated take on matching sets.

Annemiek Kessels @modeamour | Courtesy of @ayr

Maggie Winter, cofounder and chief executive officer of AYR, says the draw of an oversize button-down shirt is rooted in nostalgia, which feels comforting and accessible when dreaming up fresh outfits. “There are a number of great nostalgic style Instagram accounts, like @simplicitycity or @lostjcrew, that capture that enduring vibe,” she tells TZR. “At the same time, the classics are always recontextualized by youth culture,” she continues. “Many style accounts have featured Hailey Bieber in a pretty simple outfit: oversized white button-down, baseball cap, and black athletic short-shorts.”

Christina Abayomi, cofounder and creative director of Re Ona, and Somsack Sikhounmuong, Alex Mill’s creative director, attribute the button-down’s contemporary allure to a continued desire for elevated ease after years of comfort-first fashion. “We’re seeing an upward trend of customers opting for comfort while looking stylish, says Abayomi. “Oversized designs are the new modern-day uniform,” she continues. “It’s a fresh reminder of a ’90s classic style that’s chic and effortless — a forever wardrobe staple.”

Similarly, Somsack tells TZR, “People don’t want to wear clothing that’s overly constricting. The button-down is still polished — it can make a look casual or put together.” He points out that women love shopping the style from the men’s section. “Actually, that’s how Alex Mill started,” he says. “It was a men’s shirting company that women started buying from and loving.”

So, whether you’re looking for preppy pastels, timeless white, or bold stripes, discover six oversize button-down shirt outfits ahead for those relaxed yet pulled-together moments.

We at TZR only include products that have been independently selected by our editors. We may receive a portion of sales if you purchase a product through a link in this article

The Denim Default

Winter says you can’t go wrong with a timeless button-down and blue jeans, suggesting a mid or high-rise cut with a tucked-in shirt. “The volume on top gives a good contrast to the proportion,” she explains. “It’s an outfit you never regret and looks especially clean and classic with a one-inch-wide black or brown leather belt.”

Similarly, Abayomi tells TZR, “What’s so great about the oversize button-down shirt is that it’s transitional, looks great for any occasion, and, more importantly, is very comfortable.” When leaning into classics, the Re Ona designer says, “I love the look with jeans and loafers — think off-duty model look.” Or, try some right-now Mary Jane flats for a similarly preppy effect.

The Oversize Shirt Set

As a sweatsuit alternative that’s lightweight and breezy in the heat, Winter says it’s all about the oversize shirt set. “The cutest, comfiest way to wear an oversized button-down is with a pair of shorts,” the AYR founder tells TZR. “The proportion works, and the set is still very on-trend.”

With A Leather Mini

Abayomi says an oversized button-down shirt looks so fresh with a leather mini skirt while touching on Y2K mania, whether for dinners out, a drinks date, or a layered weekday look. Keep the aughts vibe going by adding in minimalist strappy heels and beaded jewelry.

Tailored For Work

Abayomi suggests styling an oversize style open or half-tucked over a bodysuit with high-waisted trousers when rethinking how to wear a button-down for work. Heeled sandals (perhaps in a fun color) and chunky hoops make for sleek but subtle accents with a professional air, whether you opt for yellow gold or trendy silver.

Just Dressed Up Enough

Abayomi suggests an oversize button-down shirt paired with a micro hemline, either tucked into a skirt or worn openly over a dress. The effect is perfect for an outing with friends: spruced-up but not overdone. Platform shoes keep the vibe fun and joyful when sipping your cocktail of choice (one dirty martini here, please!).

The Reworked Shirt

Somsack points to Alex Mill’s Button Back design for a fresh twist if you can’t deny yourself a modern re-worked shirt. “[It’s] a nice take on a classic and great for summer to take you to dinner or the beach,” he tells TZR. Just team it with cut-offs for lightweight linen pants and a bucket hat and you’re good to go.

The NYC-based label also just launched its new ReWork collection with sustainability advocate and owner of the community-led, zero-waste-focused IXV Coffee shop in Brooklyn, Jenny Cooper. The upcycling program repurposes unsold clothing, including pieced-together shirts featuring different bodies and arms which look particularly distinctive with white or ivory denim and chunky slides for summer.