How to Style an Oversized Shirt: Outfits You'll Want to Copy

Perfect for brunch or a casual work event, this classic preppy and polished combo layers an oversized button-down shirt under a collegiate-inspired sweater vest. Choose a fitted or slightly cropped sweater vest over barrel-shaped vests that hide your frame. We love the Quince Mongolian Cashmere Fisherman Sweater Vest for the perfect amount of structure.

A collared shirt that peeks through cleanly is the standout. Look for a fit like the crisp, easy-to-layer cotton oversized button-down Oxford shirt from Everlane.

Bottom possibilities are endless, but fitted options like straight-leg trousers, leggings, tailored denim, or a pencil skirt keep the look balanced and sleek. To bring this look to night, swap in our favorite faux leather leggings by SPANX (on discount with a SPANX promo code). Finish the look with pumps, or neutral-toned ankle boots and you’re ready to go. (Image credit: @georgia.louise1)

We love the fun silhouette of an oversized top belt-cinched at the waist over a pair of flowy, wide-leg pants. It's perfect for creative office days, dinner dates, or antiquing on the weekends. To pull this off, use a statement belt with an untucked shirt. You can't go wrong with the versatile and very belt-friendly UNIQLO Oxford Boxy Shirt, and add a UNIQLO coupon at checkout to make it a steal, too. For the right wide-leg pants for this look, be inspired by Abercrombie's tailored and relaxed pants with a high waist.

If you don't already have a bold belt, check out our list of 10 Best Designer Belts to find the perfect cincher. (Image credit: @katiejanehughes)

A sleek slip skirt brings softness and contrast to a structured and oversized top. One of our favorite office-to-evening looks, the oversized top + slip skirt combo is right at home at gallery outings, cocktails with friends, or date nights.

We recommend slip skirts with silky or satin fabrics to elevate the look and drive home fabric contrast. The body-skimming, fluid Tilda Skirt by Anthropologie does this and more. Get ready to shop with this Anthropologie promo code. 

Mango's breathable and tuckable pocket linen shirt has the perfect amount of structure. Add it to this outfit for less with a Mango promo code. Just make sure you avoid stiff, boxy tops that hide your waist fully. For breezy, casual coolness, leave the bottom few buttons undone, do a front tuck, or tie the shirt at the waist. Put the perfect finish on it with chunky gold or silver jewelry. (Image credit: @lydianoellaaa)

If you live for a coordinated set, pair an oversized top tied at the waist with matching shorts or trousers. This playfully on-trend look is perfect for rooftop drinks, a city vacation, or a summer picnic. Our current obsession is the Gap Factory matching set featuring pull-on poplin shorts and an oversized poplin shirt. We're styling it accessory-free with the shirt unbuttoned and knotted over a crop top or bralette with low-key Archies sandals. Whether you buy a premade set or put your own pieces together, commit to monochrome or matching print for top and bottom. 

One of the most versatile options for how to wear an oversized shirt is the timeless oversized shirt tucked into high-rise denim. It’s easy, flattering, and perfect for everything from running errands to plugging in for casual Friday.

Pick a high-quality ankle jean such as Levi's high-waisted jeans, for a flattering, not-too-tight fit. They're the perfect length for stylish tennis shoes like the clean classic Converse Chuck Taylor Platform. Scoop up new sneakers for the season with a DSW promo code. 

To lean into the classic aura of this oversized button-down shirt outfit, opt for the Madewell Signature Poplin Shirt that is boxy in a tuckable way. We're finishing this look with layered gold necklaces and chunkier hoops. (Image credit: @liangalliard)

This sculpted look is the perfect compromise between relaxed and refined, using a front-tucked oversized top with a body-hugging skirt. It's a great signature for office wear, networking events, or lunch meetings where the vibe is "between" dress codes. For a just-right pencil skirt, you can't go wrong with the classic and tailored J.Crew Pencil Midi Skirt. Balancing the voluminous top is the goal, so avoid loose or puffy skirts.

Think ultra-tailored, looks-like-custom for the oversized top on this one. Our pick is the minimalist and modern COS Oversized Cotton Poplin Shirt. Finally, we're finishing off this look with a pair of gorgeous VIVAIA Juliet square-toe slides that are comfortable for all-day wear, even though they're highly structured. Add a structured bag and roll your cuffs to turn office-ready.

Ready to make this outfit your own? Shop with a J.Crew promo code, COS promo code, and VIVAIA coupon for an affordable twist on the look.

Give your go-to casual look a refresh with this streetwear-inspired ensemble that layers an oversized top worn open over a sporty tank and bicycle shorts. It's perfect for travel days, errand days, or casual get-togethers—really, anytime you need a comfy style with a light outer layer.

The perfect shorts for this look are neutral or matching tones that reach mid-thigh length. We love the smooth, flawless fit of Alo Yoga's high-waisted biker shorts paired with a Skims Fits Everybody slip tank for a sleek, body-hugging base layer. Get a pair of your soon-to-be-favorite shorts in every color with this Alo Yoga discount code.

Put the final sporty touch on this with socks and sneakers or chunk slides in a neutral or matching tone. Active sneakers like HOKA are perfect for achieving the sporty, stylish look this outfit deserves. (Image credit: @aislingchan)

For a softer, pretty-in-the-daytime look, pair an oversized tee with an airy, long skirt. To pull off a romantic, boho vibe, choose a tee that's more flowy than boxy. Bonus points if the tee is long enough to be knotted at the waist or half-tucked. It's a fun, comfortable look for casual days out.

While this look works with all types of maxi skirts, we can't see it done any other way after falling in love with the romantic and whimsical Anthropologie Sheer Tiered Lace Maxi Skirt. We love the contrast of this ethereal skirt with something as down-to-earth as the popular Old Navy Oversized EveryWear Tunic T-Shirt, it's the perfect drapey oversized white tee.

In the spirit of this outfit's clean aesthetic, end with the simplistically feminine and easy-to-walk-in Quince Italian Leather Cutout Slide with breathable H-shape. Bonus tip: If you haven’t already, sign up for Quince emails for a discount on your first purchase.(Image credit: @lauri.style)

For this effortless, tomboy-chic look, tuck your favorite oversized shirt into a pair of fits-like-a-glove relaxed shorts. This outfit gets you through a full summer's worth of weekend errands, walks in the park, and cookouts.

For shorts, choose soft fabrics like linen, cotton, or lightweight denim to keep the look laid-back. We can't think of a better combo than our favorite Gap Downtown Khaki Shorts with the always-stylish Gap 100% Linen Oversized Shirt in a punchy color like super neon pink. After trying every button-down shirt under the sun, we can say this shirt was made for the half-tuck. 

Instead of searching high and low to finish this look, just go with Gap sandals, a baseball cap, and your favorite sunglasses, and checkout with a Gap promo code for a sweet deal on the whole ensemble. (Image credit: @samridhidhillon)

Look buttoned and unbothered with an oversized shirt styled with tailored pants or denim, polished loafers, and an unapologetically preppy sweater tied over the shoulders for that old-money aesthetic. This ultimate East Coast look is perfect for museum days, casual business meetings, or weekend brunch as long as you keep colors neutral, fabrics clean, and hemlines balanced. Nothing sinks this look faster than wrinkled shirts or too many layers.

While you could also go with one of our favorite cotton sweaters this season, nothing drapes as well as the thin and lovely Everlane Organic Cotton Crew. This understated sweater was made to drape over a classic like the crisp and preppy Gap Organic Cotton Poplin Classic Shirt. For accessories, we like the refined look of a gold watch or thin silver hoops. This is also a look worthy of classic penny loafers. Our choice for a non-chunky, contoured loafer is the Ubree 15 Lily with a super-lightweight sole. Get the perfect preppy shoe with a Clarks promo code. (Image credit: @arlauskaite.akvile)