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THIS SEPTEMBER, during New York fashion week, boutique owner Laure Heriard Dubreuil was at the opening of an exhibition of fashion photographer Peter Lindbergh's work. As she toured the show, she noticed that she and her companions—blogger Garance Doré and jewelry designer Aurélie Bidermann—all had something in common with his images. "We were looking at his photos from the '90s of supermodels wearing nothing but men's shirting," said Ms. Heriard Dubreuil, whose Miami store is called the Webster, "and the three of us looked at each other and laughed when we realized we were all wearing white men's shirts too." Ms. Heriard Dubreuil added, "During fashion week, everyone looks like a peacock. And there we were wanting something so basic."

Borrowing from the boys—and men—is a time-honored tradition in which some of history's most alluring women have partaken. Katharine Hepburn wore Brooks Brothers' cashmere turtleneck sweaters for most of her life. Marlene Dietrich was fond of slinking around in the same company's silk dressing gowns. Brooks Brothers was also popular (and still is) with the East Coast boarding school set. Its double-breasted boys camel coat gained a strong following with private-school girls after it first launched in 1910. It even became part of the unofficial uniform of Miss Porter's in Connecticut, the alma mater of glamorously sporty girls like Jackie Kennedy and Gloria Vanderbilt. And Coco Chanel built an entire brand by raiding her male companions' closets, nicking hunting tweeds and cardigans, which became the foundation of her singular designs.

The tradition continues today with women, like Ms. Heriard Dubreuil, who love feminine and fashion-forward looks from their favorite women's designers, but are savvy enough to source their classics—tweed coats, crew neck sweaters and button-down shirts—wherever they find the best ones, both in terms of quality and price. That is often the men's department.

Ms. Heriard Dubreuil's menswear favorites include shirts and sweaters from Dries Van Noten and jeans from A.P.C. Ms. Bidermann likes Charvet shirts, Ralph Lauren jackets and Church's shoes. London-based stylist Caroline Sieber buys her cashmere sweaters from Loro Piana's men's collection. "The fit is better and I like the round neck and loosefitting shape," she said. Ms. Sieber would also rather steal her husband's Charvet shirts than buy the French shirt brand's women's pieces, which are darted to create a trimmer shape. She recently ordered her second bespoke suit from Savile Row tailor Anderson & Sheppard, this time in tweed, for shooting weekends in the country. She calls the first one "the chicest thing she owns," which is high praise from a woman whose wedding dress was Chanel haute couture.

While trespassing into the men's department is something canny shoppers do covertly, some retailers have recently acknowledged a demand for guys' items among female customers. Barneys New York fashion director Tomoko Ogura said she regularly singles out men's items from brands like the Elder Statesman, Lucien Pellat-Finet and Fioroni that she knows will resonate with female customers and asks the brands to cut some smaller sizes. She said the open architecture of the redesigned men's department at the Madison Avenue flagship is meant to encourage shopping with fewer perceived gender barriers.

Last fall, Tokyo department store Isetan began selling women shirts from London-based menswear label E. Tautz, whose designer Patrick Grant does double duty for 192-year-old Savile Row tailor Norton & Sons. "The collection sells brilliantly," said Mr. Grant. "It's funny because it's the easiest thing we do. We make the [women's] shirts exactly the same way we make our men's—with the same fabric and cut—except for a slightly softer collar because we don't expect women to wear ties."

At J.Crew, president and creative director Jenna Lyons said the men's cashmere sweaters are a big hit with female customers, so she often requests them in brighter colors. Two years ago, Ms. Lyons introduced a women's version of the company's popular men's Ludlow jacket. The blurred gender lines are a part of the brand's DNA, Ms. Lyons explained, recalling that, when the company was run by Emily Woods (daughter of founder Arthur Cinader) in the 1990s, it offered unisex sizing. "Emily did this because she liked to wear men's clothing herself," said Ms. Lyons. That's also true of Ms. Lyons, a willowy 6-footer who has bought menswear all her life. "I went to the Saint Laurent store recently and found myself shopping off a men's rack because there were more sizes and everything was so classic," she said. "In my opinion, women should walk across the floor to men's if they want."

Saint Laurent designer Hedi Slimane has long been known for dressing ladies in menswear. He developed a cult following of chic women who loved the skinny, androgynous men's suits he made during his time at Dior Homme in the mid-2000s. Now, at Saint Laurent—where he designs both the men's and women's collections—Mr. Slimane offers unisex items, like biker jackets and combat boots.

Similarly, Givenchy designer Riccardo Tisci has included women among the models in his men's shows, acknowledging that his female clients like borrowing from his gents' collections—and even vice versa. His printed men's T-shirts have become particularly popular. "It started as men's, but it naturally became unisex," said Mr. Tisci. "If a man wants to wear a skirt and a woman wants to wear a bomber, it should be like that."

That's heartening for a woman who appreciates the slouchy cool of Mr. Tisci's men's tops. However, aesthetics aren't the sole factor at play. Many women dip into the men's department because they can buy high quality clothes at far more reasonable prices. For instance, when Mr. Grant initially told the Isetan staff what he'd like to charge for each shirt (around $275), he said they were surprised. "They were like 'Oh my god, this is so cheap!' " he explained. "They have equivalent shirts from [women's brands] which are 50% more expensive, and the quality isn't as good."

"Men have a lower tolerance for high price tags and expect higher quality," Mr. Grant explained. "They want to buy a sweater and have it last forever."

Jason Basmajian, the new creative director of Savile Row tailor Gieves & Hawkes, agreed that women get a raw deal on prices. "Our bespoke suits start at around $6,500. Try getting couture for that little!" he said. The British brand is known for catering quietly to a small, elite group of ladies including Queen Elizabeth and Princess Diana. More recently, pianist Rosey Chan was fitted for a bespoke tuxedo. "A lot of our customers' wives come in to pick up an order and realize they could have a camel coat or blazer tailor-made for less than they'd pay off the rack for a women's equivalent."

Ultimately, what the two sexes want to wear may not be that different. "Recently a journalist asked me to make up a list of what every man and every woman should have in their closets," said Ms. Lyons. "I laughed when I realized that the lists I'd made were exactly the same."

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