Wear a White Shirt Under a White Dress Shirt Styleforum

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In the world of wardrobe staples, there is one undisputed queen: The white button-down shirt. It lends a crisp confidence to casual looks, a quiet swagger to the workplace uniform, and a masculine touch to formal frills. But timeless needn't be basic—we asked five stylish New Yorkers to show us how to put a personal stamp on the classic. Let the reinvention begin.

The Boss

There's no denying the white shirt dominates many an office, but you have to choose the right one for the job. "If you're looking to wear your white shirt in a business setting, choose something fitted, so it will stay neatly tucked in and not bulge out of your pants or skirts," says Town & Country Fashion Market Editor MaryKate Boylan. "You want something that looks good under a jacket, so it gives you options." She also recommends keeping the cuffs buttoned (rather than rolled) for an irrefutably in-charge look.

Choose something fitted, so it looks good under a jacket.

"White shirts never go out of style. They are classic, but can each be so individual at the same time," says model and entrepreneur Lana Ogilvie, pictured here. "I wore my favorite white shirt until it disintegrated. It was by Helmut Lang and I bought it in the '90s. You really can't go wrong with a white shirt."

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The Weekender

White shirts can add a much-needed dose of structure to relaxed jeans and flats. To amp up the cool, trade in the standard, long-sleeved button-down for a more daring version. "I like to look for unique moment in a white shirt," says Boylan. Think: exaggerated collars, contrasting buttons, seaming details. A tailored short-sleeved version or a tie-waist tunic style, like these seen here on entrepreneurs Jessica Joffe and Alison Bergen, look polished enough for a low-key lunch meeting, but easy-going enough for Sunday brunch.

Look for unique details: Exaggerated collars, interesting sleeves, contrasting buttons.

"A shirt is a canvas: it is seasonless, ageless, and in our case, sizeless," says Joffe, who co-founded Même Chose, an inclusive new line of shirts, with Bergen. "Shirts also telegraph authority. Shirtwaists, the earliest incarnation of the women's shirt, liberated women, allowing them to move freely and work outside the house and demand the vote."

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The Night Out

Is there any look more effortlessly chic than a man's white shirt with an ultra-feminine skirt? The pairing not only offers a visually pleasing contrast, but also has an "I borrowed this from his closet" sultriness. "Carolyn Bessette, Sharon Stone, Carolina Herrera, they've all done it," says Boylan. "It's the perfect formula for an evening outfit; you can always rely on it." To bring the disparate elements of your look together, choose a slightly oversize man's shirt, tuck it in, and top it with an eye-catching, wide belt that accentuates your shape.

Choose a slightly oversize man's shirt, tuck it in, and top it with a wide belt.

There's still room for sartorial innovation, though, as seen here on Haniya Riaz Khan. In a cheeky twist, the bottom of the shirt is visible below a tulle skirt, designed by her father-in-law, Naeem Kahn.

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The Cool Girl

When it comes to pushing the fashion envelope, think of your white shirt as a safety net: No matter what else you pair it with, a classic, long-sleeved button down will bring a polished, grown-up sensibility to your look. "When you want to have a little fun with your white shirt, add a camisole or even a bustier," says Boylan, who points to Clueless's Cher Horowitz as her inspiration. "Or you could go the opposite way and wear a turtleneck or tee with a white shirt that's open at the neck."

Think of your white shirt as a safety net: Wear it under a camisole or over a thin turtleneck.

Pairing it with a tweed mini skirt and sneakers, as DJ Tessa Hilton does here, keeps the style youthful, not to mention comfy.

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Meet the Models

Lana Ogilvie

Scouted in a high school fashion show in her home town of Toronto, Lana Ogilvie became a top model in the '90s, walking the runway in Paris, Milan, New York, and London. The first model of color to sign an exclusive contract with CoverGirl, she has appeared in Vogue, Elle, Sports Illustrated, and Harper's Bazaar and has been photographed by Steven Klein, Lord Snowdon, and Bruce Weber, among others. In addition to working as an on-air personality, Ogilvie has launched Sabre, a line of handmade jewelry, and an eponymous skincare line targeting the needs of mature skin.

See the Boss Again

Jessica Joffe and Alison Bergen

Même Chose founders Jessica Joffe and Alison Bergen first met while working for "the godmother of empowerment dressing" Diane von Furstenberg. "We were kindred spirits immediately," says Joffe, "both fascinated by what we understood then to be the long overdue shift in the industry and how much work still needed to be done." Together, they formulated the idea for an accessible, size-inclusive brand of clothes that would make women feel and look empowered. They launched their line with a range of shirting styles in March 2019.

See The Weekender again

Haniya Riaz Khan

She may not usually be found in front of the camera, but fashion- and beauty-industry veteran Haniya Riaz Khan is no stranger to the stylish life. Having started her career in public relations, she spent several years managing industry-leading fashion stylists, hair stylists, and makeup artists as an agent at the Wall Group before becoming a brand consultant. She currently resides in Brooklyn with her husband, Zaheen (her father-in-law, Naeem Khan, designed her wedding dress), and 19 month old daughter, Kaia Noor.

See The Night Out again

Tessa Hilton

Tessa Hilton graduated from Bard College with a degree in Literature and Computer Science, but she didn't find her true passion until she fell in love with techno and house music. Between modeling gigs for brands like Alice and Olivia, she's a DJ and music producer, and recently formed the DJ duo Humanmosiac with her husband, Barron Hilton. In addition to being a multi-hyphenate, she's multilingual: Though she was born in Manhattan, her first language is French, followed by English and German, courtesy of her French/Danish mother and German father.

See The Cool Girl again

Photos and videos by Tyler Joe; digital assistant: Alex Lopez; photo assistant: Shadi Best. Graphic Design: Michael Stillwell. Styled by MaryKate Boylan; styling assistant: Nicole Ross. Hair by Leonardo Manetti; makeup by Marygene; nails by Gina Viviano. Digital Director: Elizabeth Angell. Chief Visual Content Director: Alix Campbell. Visual Director: Darrick Harris. Bookings Director: Steven Brown. Producer: Sameet Sharma. Special Thanks to Lotte New York Palace.

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Source: https://www.townandcountrymag.com/style/fashion-trends/a28676205/how-to-wear-white-button-down-shirt/