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In spite of Marlene Dietrich and two generations of pantsuits, there remains something subversive about women wearing men’s clothing. This season, amid the preponderance of appliqued flowers, bows, sequins, ruffles, and ribbons tumbling off the runways, a look that elevates elegance over girlishness is more subversive – and refreshing – than ever. As an old French proverb puts it, “Whoso doth the breeches wears a life as free as air.”So when I heard that Ralph Lauren was opening a boy’s shop on October 8, just across the street from the Polo Mansion on Madison Avenue (878 Madison Ave., 212-606-3376), I jumped at the chance to explore the land of tweedy little men. The clean lines of a wool pinstripe suit, I reasoned, might serve as a welcome antidote to all those brooch-covered cardigans. A boy’s size 16 is roughly a woman’s size 8, and at a quarter of the cost of grown-up duds – $375 for a wool blazer that retails for $1,195 at the Polo Mansion – it would be foolish not to take a look.It turned out I wasn’t the only woman thinking about boyswear. Just as the manager confirmed that women have indeed been visiting the shop, a petite blond caught my eye. Annie, who works in Ralph Lauren’s advertising department, was modeling a handsome brown-and-white wool blazer in front of a mirror. “I always have worn boys clothing,” she said. “I just get it tailored if it doesn’t fit perfectly. Sometimes the arms are too long or short.”A trip across Madison Avenue to the Polo Mansion revealed similar events. I could have sworn that a saleswoman on the home fashion floor was wearing the same boy’s black-and-white wool jacket I had tried on across the street. Upon inquiry, a different saleswoman confessed to shopping at the boy’s shop as well, for sweaters and rugby shirts and blazers.New York offers no shortage of tailors, but Luigi New York (177 Seventh Ave., 212-243-7855) is especially good for custom restyling and alterations. You can bring him your father’s preppy college clothes and he’ll rework them for you. If you have sentimental items or collectible vintage clothing that you want to render wearable by sizing down or up, you can hire Ellen Christine of Ellen Christine Millinery (255 W. 18th St., 212-242-2457) for a consultation. For approximately $150 she will advise on how to rework clothing and achieve the right fit for the garment in question. She’s especially good at Victorian and Edwardian pieces.Next I paid a visit to the venerable firm Turnbull and Asser (42 E. 57th St., 212-752-5700). No stranger to women, the British firm, known for its impeccable service (as well as dressing Prince Charles), has much to offer. “We have made custom ties for women,” explained Kevin Hill, an associate. Of course they offer everything else as well, including a suit program in both made-to-measure (based on their own proportions) and bespoke (you have your very own “block” from which the suit pattern is derived, ensuring a perfect fit). Jackets, pants, waistcoats, and skirts, even tuxedos, can be made for women. “We recently did a tuxedo shirt for a singer,” Mr. Hill said. “We did the front in classic white but the back was striped.”Granny’s tweeds, even those interpreted by Marc Jacobs, master of vintage redux, can’t compete with that kind of chic. With shirts starting at $290 I didn’t bother asking the starting price for made-to-measure suits. But I was thrilled at the idea of choosing linings, cuffs and collars, buttons and closures, and monogramming. Women have been missing out on this type of refined embellishment.Turnbull and Asser also specializes in ascots ($140), which can be a wonderful way to dress up a sweater. An ascot, unlike a neckerchief, is tailored to fit; the fabric around the neck is thinner than the rest, forming a neat, comfortable circumference, so that the graduated fabric falls in abundant luxury. Securing the loose, romantic folds with a tie pin or brooch adds feminine dash. Were ascots popular with Turnbull and Asser’s female clients? Mr. Hill has noticed an upsurge in interest, but not in tremendous numbers, which is shocking considering the range of choices, with more than 50 unique colors and designs to choose from. All in silk, of course.At $90, ascots in paisley, solids, or dots run for a little less at Ascot Chang (7 W. 57th St., 212-759-3333), a quaint, below-ground shop directly beside the Chanel boutique. (The store also offers bespoke women’s shirts starting at $90.) A quick stop into the men’s department at Saks revealed a fairly paltry selection of Brioni ascots – the conservative dot, check, and paisley motifs were available in equally conservative colors: blues, yellows, and reds. They cost $170 but can be won on eBay for much less.The finishing touch for any menswear outfit is sexy hosiery. My favorites are the designs by Wolford (122 Greene St., 212-343-0808). There is nothing like the peek of a black checked stocking peering out from a trousered leg, or better yet, cropped trouser.

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Back to Breeches

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