My immersion into the menswear landscape happened fast. Within a couple of weeks of accepting a job overseeing the beat for a luxury title—after more than a decade covering womenswear—I was bound for Pitti Uomo.

A biannual industry trade show, Pitti has outgrown the walls of the fortezza that houses it, spilling into the narrow streets of Florence in an influencer-heavy scene of suiting aficionados determined to out-peacock one another—100-plus-degree temperatures in June be damned. But among the occasionally over-the-top spectacles, an invaluable sartorial shift occurred.

I’d long been drawn to tailoring when wanting to feel particularly pulled together, no doubt a result of the ease of the school uniform I wore during my youth. As a fashion journalist, then so focused on writing about trends, I couldn’t fathom having the time or inclination to embrace suiting.

Even so, I was far more likely to pair a blazer with jeans. A full suit?

It felt wildly archaic and, if I’m being frank, a bit boring.

Those notions faded en route from Florence to Milan for the menswear shows, where I first caught a glimpse of my male colleagues’ impossibly minuscule suitcases. The “secret” I would soon learn was in the suiting, which they mixed and matched with aplomb over the course of nearly two weeks.

It was enough to convince me I needed a suit of my own. When the time came to commission it, I knew Savile Row’s Caroline Andrew, whom I’d met at a Pitti dinner, was the perfect tailor for the job.

“Right now, about 30% of my clients are female, many of them in the U.S.,” Andrew tells me. It’s an impressive figure given that, on “the Row,” bespoke tailoring has historically been a service geared toward men.

Not every house is even accustomed to cutting patterns for the female form. Among Andrew’s clientele, she counts jewelry designer Jessica McCormack, gallerist Louisa Guinness (it was from her namesake gallery that Kendall Jenner procured those Alexander Calder earrings), and Fiona Dreesman of popular Belgravia homewares boutique Fiona’s Finds.

Those same clients are also often looking for something a bit left of center. Where most tailors on Savile Row have a strict house style to which they adhere, Andrew keeps an eye on fashion and has a willingness to collaborate.

“Suiting for me is like a uniform,” Dreesman tells me, noting also that bespoke ensures perfect sleeve lengths for her tall frame. “I get up and don’t have to think about things going together.

It is chic and sharp and you are always well dressed from day to night.”

A bespoke Savile Row suit is an investment purchase—semi-bespoke suits start at £3,000 (around $4,000) and fully bespoke at £5,000 (roughly $6,600) and are entirely handmade. My goal: a single garment to get me through formal occasions during the festive season, rather than multiple evening dresses which take up precious New York City closet real estate.

Looking ahead to the fall (start to finish, it is roughly a six-month process with three fittings), I decided on a tuxedo. While the sheer number of options can be overwhelming, it was an easy decision, but one that begged questions of lapel widths, buttonholes, fabrics, and trouser length.

I decided to spare myself the stress and defer to Andrew (highly recommended).

We landed on a double-breasted number with a hidden placket, which felt a bit more modern, in black wool barathea—the most traditional of tuxedo fabrics—with a silk-satin peak lapel and jetted pockets. At this stage, our first fitting, there was of course no garment to speak of, other than those on a mood board I’d put together.

Countless measurements were taken, and it was decided that the coordinating trousers-to-be would be a slightly wide straight-leg style with satin tape running the length of the outside hem. With no need for belt loops, Andrew added tonal side adjusters.

A few months later, Andrew was back in New York, and the tuxedo was taking shape. With the intricate stitch patterns and horsehair “canvas” visible, it was impossible not to marvel at the work and training required for the construction of such a garment.

Apprenticeship lengths range from two to six years, with the lower end being for those specializing only in the making of trousers. Andrew blazed her own trail, navigating a scene that was then very much dominated by an old boys’ network.

She earned her degree at the London College of Fashion and interned at Burberry, Edward Sexton, and Henry Poole.

When I met up with Andrew in New York in mid-September for the reveal, I could not have been more thrilled with the result. (For those who can’t make it to London, Andrew maintains a robust trunk-show schedule in the States.) Beyond the exterior, customized to your preference and precise measurements, the interior architecture is like nothing you’ll find off the rack.

A canvas of horsehair and wool placed between a jacket’s outer and inner lining will mold to a wearer’s figure over time, ensuring it hangs and moves perfectly and endures for decades. Clever seam allowances enable alterations, should one’s weight fluctuate.

“Having bespoke means I am never walking into a room wearing the same as anyone else. It is timeless,” says Dreesman, who enjoys adding individual touches such as six buttons on her jacket sleeves.

Since my initial meeting with Andrew, much has changed. My Pitti Uomo days are behind me, and instead of running around Fashion Week, I’m navigating the maze that is the D&D building as an interior designer—often in tailoring now that the weather has turned cooler.

Curiously, I find myself enjoying the process of getting dressed more than I ever did when fashion was a full-time job. Perhaps it’s the ease of suiting as much as the challenge of something “new.”