With Alexander Kraft’s assertion that he’ll never be “caught dead” in a T-shirt, you’d be forgiven for thinking globetrotting might not be at the top of his agenda. On the contrary, the acclaimed style icon and CEO of Sotheby’s International Realty France-Monaco is always on the move. He just does it in bespoke Cifonelli.

Alexander Kraft wearing Cifonelli.

In addition to his work commitments, Kraft frequently travels between his regular residence in Monaco, his country house in Provence, and his pied-à-terre in Paris, rarely packing more than a carry-on—even for long-haul journeys. The trick is not just what you pack, he says, but how you pack. Cotton T-shirts may roll into conveniently small units, but: “I had an English butler who showed me how to fold [my] suits so they don’t arrive wrinkled,” Kraft explains, allowing his elegance to remain intact. Depending on the journey, he picks one or two different suits—as well as the one he’s wearing—that can be mixed and matched. Most importantly, he selects them in fabrics such as flannel, which doesn’t crumple or rip in transit.

“Some people think I was born in a three-piece suit, but that’s [just a] rumor,” Kraft muses, although a scroll through his Instagram feed would lead you to believe it. He is a connoisseur of men’s clothing, but his understanding of all things sartorial doesn’t make his style predictable: “You should know all the rules, but you also should know how to break them,” he declares. However, not everybody has the same rebellious approach to fashion. After all, he is first and foremost a businessman, and his associates are often taken aback by his cavalier slants on tradition. But Kraft—who acquired Sotheby’s International Realty France-Monaco in 2004—pays no mind to those who suggest only black lace-ups are suitable in the boardroom, often pairing his suit with polished, tasseled loafers instead. He does own the company, after all.

It was this uncompromising attitude that led Kraft to find an affinity with Cifonelli, the Paris-based tailor for which he is brand ambassador. Quietly boasting French tradition, Italian lightness, and English structuralism, cousins Massimo and Lorenzo Cifonelli have an eagle eye for detail, even more so than Kraft himself. “They rip the jacket off your back and don’t give it back to you until they think it’s perfect,” he says of his experience going for up to ten fittings for a single suit. When your clothes are cut and sewn by hand so meticulously to your own measurements, it’s no surprise that even something generally considered constricting can become “as comfortable as pajamas,” as Kraft puts it.

This finely tuned aesthetic sensibility goes beyond how he presents himself. To Kraft, “style is the outer expression of the inner personality.” With this in mind, working in the realm of luxury real estate is a natural fit for a man who is often asked whether he has chosen his outfit to match his dog. He is aware that he is prone to certain palettes and silhouettes, and he knows that on a subconscious level this reflects itself in the world he has created around him, whether he’s playing the piano at his country home or representing Cifonelli in a double-breasted waistcoat. Life may get hectic for this CEO, but Kraft never loses sight of his extraordinary attention to detail—down to his handmade Italian socks.

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