HOW TO STYLE AN OVERSIZED SHIRT: OUTFIT IDEAS AND STYLING TIPS

Comfortable and understated, oversized clothing has become a go-to for many. The right combination of garments and accessories can elevate any look and lead to a self-defining style. 

Learning how to style an oversized shirt allows for the ability to turn everything from spacious button-downs to baggy T-shirts into fashionable wardrobe staples. Knowing how to play with proportions and accessorize smartly makes creating an oversized shirt outfit easy.

TIPS FOR STYLING AN OVERSIZED SHIRT

For both street-style mavens with a finger on the pulse of fashion trends and romantic minimalists who stay true to their roots, balanced outfits are born from the perfect combination of bottoms, outer layers, accessories, and footwear. Here are eight ways to create a look that works:

Oversized button-up + straight-leg jeans + heels

There’s nothing quite as classic as a loose-fitting button-up tucked into a pair of straight-leg jeans. Giving the shirt a gentle half-tuck walks the line between casual and dressed-up. Choose a white or solid button-up to create an outfit with uncomplicated sophistication, completing the look with strappy heels, gold earrings, and a designer watch.

Long-sleeve silk shirt + matching pants + heels

A coordinating silk ensemble is effortlessly chic, and the power is all in the print. Colors, patterns, and textures create impact and dimension. Single neutral tones are timeless, while bold colors and prints can be worn together or mixed and matched with solids for maximum versatility. Pair an oversized set with heels, thin stacked bracelets, and a soft leather clutch.

Oversized designer T-shirt + baggy jeans + statement shoes

Pairing oversized tees with baggy jeans is a look that never goes out of style. To accentuate the figure and elongate the legs, create a light French tuck by slipping the front of the shirt behind the waistband at the belly button, leaving the rest of the fabric untucked. Wear streetwear sneakers or knee boots with a small handbag, sunglasses, and bold rings to complete the classic combination.

Oversized tee + mini skirt + ankle boots

Oversized graphic tees worn with mini skirts and ankle boots evoke a cool streetwear vibe. Try a mini skirt that’s leather, denim, or tweed, and complement it with an artful or vintage-inspired graphic tee. For an edgier look, slip on a black oversized leather jacket and dark sunglasses.

Blazer + button-up + tailored pants + heels

Combining two oversized pieces is the ultimate chic look. Pair a roomy blazer and button-up with tailored pants in a monochrome color to redefine the power suit. Add feminine touches, such as heels and statement jewelry.

Oversized top as a dress + denim shorts + sneakers

A long oversized shirt can double as a dress. Pair a subtle earth-toned shirt with a wooden clutch or a bold-colored shirt with a structured handbag. Wear biker shorts underneath for comfort and coverage. Opt for white sneakers to keep things casual, or slip on a pair of over-the-knee boots for a statement look. 

Oversized button-up + turtleneck + heels

An uncommon yet fashionable duo, button-ups, and turtlenecks make an exquisite pairing. Style the look with monochromatic tones, or have fun with playful contrasting colors. Choose a slim-fitting turtleneck that allows room for the button-up to drape gracefully overtop without appearing bulky, and finish off the outfit with chunky hoops and heels.

Short sleeve + shorts + loafers

A coordinating shirt-and-short set makes for a refreshing summer outfit. Ensure the pieces are loose-fitting, comfortable, and made from lightweight natural fabrics. Complete the look with earth-tone leather loafers and a canvas tote bag.

7 DESIGNERS THAT CREATE FANTASTIC OVERSIZED SHIRTS

From the best oversized T-shirts to beautifully designed button-ups, these seven designers understand what it takes to create the perfect extra-roomy top:

The Row

The Row creates sophisticated, well-tailored designs that complement refined, minimalistic styles. The label’s oversized button-ups are made from gorgeous fabrics that are cleanly cut. Each button-up comes in a subtle hue, mirroring the brand’s commitment to timeless design.

Another Tomorrow

Another Tomorrow crafts elevated pieces guided by a deep commitment to human, animal, and environmental welfare. The label’s ready-to-wear collection uses responsibly grown materials and ethical manufacturing, with each piece designed to enjoy a long life. The oversized button-front shirts are made from sustainable fabrics, including super-fine ethical merino wool and organic cotton. Pair the sophisticated designs with sleek pumps and elegant jewelry.

Marni

From joyful hand-drawn illustrations to exotic prints, Marni takes an artistic approach to fashion with eclectic accents and an emphasis on individuality. The brand’s loose-fit graphic tees feature youthful silhouettes with roomy sleeves and crew necklines. Pair the tees with colorful mini skirts, shorts, blue jeans, and laid-back sneakers.

Ganni

The cute oversized shirts from Ganni feature bold, punchy logos, lively illustrations, and statement smiley faces. Most of the label’s tees meet the Global Organic Textile Standards (GOTS), constructed from sustainable materials like organic cotton. 

Palm Angels

What first began as a photographic documentation of California skater culture has become one of the most widely recognized luxury streetwear labels. From classic high-neckline logo collar tees to boldly printed button-ups, it’s no surprise that Palm Angels rocks the oversized clothing world. With spray-painted motifs, a gothic-styled logo, and iconic palm trees, putting together a head-turning ensemble is as easy as tucking a Palm Angel top into distressed jeans and throwing on a pair of skater-style sneakers.

Masai

Masai carries an assortment of relaxed shirts in versatile shapes and classic patterns. Each piece is designed to capture free-flowing femininity through soft fabrics and generous cuts. The prints are intentionally designed to carry the wearer through every season with colors and patterns to suit any weather. 

Loulou Studio

Loulou Studio creates timeless styles in soft, luxurious fabrics, like cotton produced in Portugal and cashmere sourced from Mongolia. The versatile pieces are delicate and feminine, presenting airy, voluminous silhouettes. The label sources ethical materials and is committed to creating a limited impact through sustainable fabrics and plastic-free packaging.

LOOKING FOR THE LATEST STYLES?

Neiman Marcus carries luxury tops and bottoms from the best designer brands, with new arrivals every season. Book a one-on-one in-store or virtual appointment for tips on styling an oversized shirt and other styles.