HERE' THE SITUATION, with apologies - for a variety of reasons - to those it doesn't describe:
....You have just been recruited by one of the new hot dots, a Web startup with a very cool idea. Incredibly, no one else seems to have thought of this new thing yet, so the prospects are promising. The salary isn't huge, but the deal includes a nice chunk of pre-IPO stock. And you've been given a signing bonus of $20,000. Nothing close to what you'll be worth one of these days, but entirely liquid and instantly spendable.
....There's one small catch. In your past Silicon Valley (or Alley) gigs, you've worked long hours wearing the full Palo Alto - khakis, sweatshirts and a pair of out-of-breath Air Jordans. You haven't bought any serious clothes since you headed off to college. Now the new job will mean trips to Europe and Japan to lin up partnerships and sweet-talk investors, in places where geek chic simply will not do. So, since you're starting more or less from scratch, an entire new wardrobe is needed.
....Because this is not the renovation of an existing collection of clothes but a construction from the ground up, let me suggest a radical approach to spending that $20,000. Rather than struggling through the hit-or-miss process of going into one retail store after another, hoping to find salespeople with expertise and imagination, why not let a great tailor take on the entire job? In the end, it will take less time, that precious commodity you never have enough of. And though the per-item costs will be higher, you'll be able to rise above the minor fashion trends that can age a wardrobe before it's time. Also, you'll get the kind of psyhosartorial advicefew retail salespeople are able to give. After the initial minor annoyance of fittings, you will be the owner of clothes that give you major bragging rights, even if you nobly choose not to gloat - except perhaps by discreetly showing off the well-bespokeness of jacket-sleeve buttons that work.
....Seeking the best possible consiglieri for assembling a feast of classic made-to-order clothes, I asked three of America's top tailors, two in cities famous for leading-edge tech in both software and E-commerce and one in a great midwestern center of traditional business, to put together a la carte menus of the pieces they consider essential to great dressing. These master tailors are Leonard Logsdail in New York, Gian DeCaro in Seattle and Chris Despos in Chicago.
....Starting in New York, a city renowned for male plumage, we visit Logsdail at his shop on the fourth floor of 9 East 53rd Street in Manhattan. His assignment is to provide us with a small, enviable wardrobe of a few high-end pieces. The man's accent implies Savile Row roots, and in fact, Logsdail began working for some of London's classic suit makers at the age of 19. "I was sacked from three of my first four jobs," he says, "because I thought I knew better than anyone else. When I went out on my own, I still figured I knew it all, so I was making suits that customers were sending back. It's a Darwinian world, and those are expensive mistakes, so now I've learned to listen."
....Logsdail's house style might be described as Brit limited, with some shape in the waist and a little shoulder padding, but subtle enough to withstand trends. He believes in making a little go a long way; if he's not going to fill a closet, he's determined that each piece can be as useful as possible." He now tends to use wool fabrics in the eight to ten ten-ounce range, what is known as "nine-month weight."
....Starting with jackets, Logsdail suggests a blue worsted spuncashmere blazer. "It's not as traditional as doeskin cashmere," he says, "but it's very elegant to wear." You touch a bolt of cloth. As Mike Myers's "Coffee Talk" yenta might put it, "like buttah." Logsdail also recommends another cashmere jacket, in a subtle houndstooth check. "With a couple of pairs of trousers to complement both jackets," Logsdail says, 'you've made a good start." One jacket will cost $4,200 - enough for eight off-the-rack standard blazers maybe, but put on a jacket like this, sculpted to your torso to the split centimeter, and you will be reminded, dramatically, that you get what you pay for.
....Also on the Logsdail list: two suits, neither with a strong design. "If someone doesn't have a lot of clothes, you don't want people to remember him as 'the guy with that blue striped suit.' "
Instead , you end up with one medium gray with a soft chalk stripe or a subtle gray check, and one dark blue with a faint color accent that can be picked up with the right shirts and ties. Logsdail likes to use super-150 wool, not cashmere but of "cashmere quality." The suits will also set you back $4,200 per. Add two pairs of trousers, also nine-month weight, with whatever pleat scheme you want, each for $1,000, and you small but exquisite wardrobe comes to $19,000. With maybe four custom shirts from Clarvet, your signing bonus has been converted into clothes you'll wear for the next ten years.
....Off to Gian DeCaro's bright, elegant ground-floor shop on First Avenue, just a block uphill from the Pike Street Market in Seattle. DeCaro, a past president of the Custom tailors and Designers Association of America, is a second-generation tailor whose father came from Calabria, Italy. DeCaro is the man who, one wardrobe at a time, is bringing civilization to the mix-and-mismatched walk-in closets of Microsoft millionaires -up to the Man himself. On any given day, young men with nerd-to-natty dreams walk in and let DeCaro take on the job of needle-and -thread therapist. Like any other therapist, the master tailor will ask questions to find out whether his client has a real interest in clothes (which will lead DeCaro to be more adventurous) or is being prodded by a spouse or girlfriend (which calls for a more conservative approach). DeCaro's house style is classically Italian, with soft construction, side vents, ticket pockets and usually, three buttons. With custom tailoring, however, everything is negotiable (hence, "custom"). For our twenty grand, I asked DeCaro to create as many pieces as he could without sacrificing quality. Here was his approach.
....We start with a straightforward three-button suit, in charcoal rather than black "so that brown shoes can be worn." Price: just under $2,000. Next, a classic blue blazer, three pairs of light wool trousers, deep gray, mid-gray and tan "with a golden tone." Every man, DeCaro states with reassuring certainty, needs a beautiful midnight blue suit, "for those times when you have to make a quiet but persuasive impression." Gazing into the middle distance, DeCaro does some mental calculations. Basing his numbers on his best fabrics, he figures we're up to around $10,000.
...."I'd recommend spending the rest on elegant, rich-looking sports coats, to be worn with those tan and gray trousers. Worsted cashmere, mustards and deep browns and olives with hues of gold, cream, maybe a Prince of Wales plaid - the kind of things a true boulevardier in Venice wears in early fall. Three or four of those. For spring I'd make up a dark blue blazer in a wool-linen-and-mohair-blend hopsack. Now we're edging up on $20,000, but there's enough left for some really fine shirts." DeCaro isn't a fan of plain vanilla. "If you just want a dozen white shirts because they're easy, you automatically limit your sport-coat wardrobe." Maybe white shirts are too reminiscent of the old IBM for the man who dresses the new Microsofties. He suggests only three in white broadcloth, plus at least four blue shirts "because of their versatility" and some checks and subtle plaids. As $255 apiece, twelve shirts come to #3,060, putting us at or a bit above our budget limit. Oh, what the hell! Make the shirts of 140-weight cloth from Thomas Mason, pay $295, and know true inner peace.
....According to Chris Despos, one budget-busting addition is worth considering. Especially if, let's say, your new job is at a law firm, not an Internet start-up. Despos, who has been making clothes for men in Dallas for nineteen years and has recently opened up a shop at 24 East Oak Street in Chicago, strongly recommends a great tuxedo. "Since black-tie is still called for at really important events," he says, "that's where it's really important to stand out." The difference is huge between a %60-a-night rental, or even a good off-the-rack tuxedo, and one that's made to fit perfectly and subtle express individuality. "Nothing shakes a guy's confidence more," says Despos "than to be a t a formal dinner with the major players in his business knowing that last week his tux was at the prom." Despos admits that a luxe tux might have to wait for that first big year-end bonus, since one in black super-100 wool and kid mohair (single-breasted, one button, peaked-lapel) will cost $3,700, but he hopes you won't forget.
....Despos describes his house style as a blend of English and Italian, with a relaxed shoulder and shaped waist. The pretux Despos wish list runs like this: four high-end suits at $3,200 each - a blue beaded-pinstrip single-breasted, two shades lighter than navy; a charcoal gray sharkskin double-breasted; a navy blue pindotted single-breasted one-button (what Despos calls a "transition suit," which works both for the office and evening); a windowpane plaid in blue over muted brown, three buttons, side vents (able to be worn informally with a wool polo pullover and brown suede shoes). Two sport coats, one in a vicuna shade with a subtle red windowpane decoration ("terrific with gray flannel trousers and a French blue shirt"), at $2,600, and one high-twist navy blazer that Despos cuts with a high waist, for $2,400. Add five pairs of slacks: charcoal gray worsted, $625; taupe gabardine, $625; olive twill, $575; custom khaki ("the Dockers of your dreams"), $425; and medium brown corduroy, $425. And there you are, at $20,475. A bit over budget, but, oh my, you do look fine.
....As you step out, beautifully dressed but barefoot, you'll realize we didn't include custom shoes. But a full array of custom-made footwear is something we'll deal with on another day, with another twenty G's.


Reprinted with the permission of GQ Magazine