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A Great White

The story of one man's search for the shirt of a lifetime.

I've given up trying to divine whether women can ever be too rich or too thin. But for men—at least for myself—I do know this: You can never have too many white shirts. And for far longer than I should really admit, I have been obsessed with finding The One, what I'd call the great white shirt. I know it's out there; I am determined to find it. Call me, um, Ishmael. Here is the tale of my quest.

PRADA

I really, really don't want to use the word "genius." But I can't help myself when it comes to Miuccia Prada. What's to like? The cut is slim through the body, so you have none of that extra cloth hanging over your pants, making you look like a weary congressman. And just when you think that would make the shirt too binding, you realize it's still cut fuller in the armholes, allowing an effortless range of movement. The collar looks great with a tie or without, so you can wear the shirt to work and then ditch the tie and be ready for a night out. Made of supremely soft material that feels great against the skin, with a tight weave that makes the fabric look extra crisp and smart, this is a shirt that looks right with a suit or a pair of 501s—as I recently wore it on a date one summer evening in Montauk. It's the ultimate in versatility.

FIT Trim and sexy.
FOR Every occasion. Looks as good with a suit as it does with jeans.
PRICE $340; 888-977-1900.

HELMUT LANG

I bought a black Helmut Lang overcoat a couple of seasons back that I absolutely love. But the two shirts I tried didn't work at all. One, a classic point collar, looked promising at first: thick, crisp cotton and a second button that let the collar open at a perfect place on my neck. But further investigation exposed an elastic band that ran behind my back and connected up at my elbows and another set that connected the cuff to the elbow. Fine for an extra in Cabaret, but definitely not for me.

FIT Snug.
FOR A Flying Wallenda.
PRICE $325; 212-334-1014; www.helmutlang.com.

The second, much sheerer and blousier, made me feel like an 18th-century aristocrat. Then there were the drawstrings in the back. Yes, drawstrings. They were a good 18 inches long and they cinched up the bottom of the shirt, and I had to tuck them into my pants. All I could think about was not doing it correctly and looking like an unraveling mummy. Not a bad shirt, just more for a Daniel Libeskind kind of guy.

FIT Loose.
FOR The artistic sort. Or those who can deal with loose ends.
PRICE $370.

BROOKS BROTHERS

After chasing after the whole "business casual" mess, Brooks Brothers is back to its roots, creating solid, great clothes for businessmen. The result: their Golden Fleece white shirt. Cut along the basic Brooks pattern—full arms and low armholes—it's thankfully not quite as full as the shirts of ten years ago. Made of two-ply Italian cotton, it's Brooks' best and perfect for business. Which might be my only complaint—the collar looks great with a tie, but without a tie and the top button buttoned, it just doesn't work. Which is not a problem, unless you want to wear it on weekends with jeans.

FIT Traditional and roomy.
FOR The man who wants an American classic, but always remembers he's living in the 21st century.
PRICE $225; 800-274-1815; www.brooksbrothers.com.

BANANA REPUBLIC

At $68, Banana Republic's Luxe Collection shirt is a great deal for a reliable, everyday standby. Which is where it would have to end for me. The problem comes down to sizing. The shirts are offered in sizes from XS to XL, and the sizes are inexact. Especially in the sleeves. The M is sized 151Ž2 x 34 and I'm a size 151Ž2 x 35 with especially long arms. As I sit here typing, the cuffs have slid about two inches past my wrists—not a good look, especially under a suit coat, where I like to show some cuff. Still, it's a good shirt, for a great price, and looks like it will wear nicely.

FIT Full, but not too baggy; best of both worlds for the average guy.
FOR Everyday casual.
PRICE $68; 888-277-8953; www.bananarepublic.com.

JIL SANDER

Jil Sander has always been about the purity of design, so I was confident she would master the purest of items—the white shirt. Hers is cut slim and narrow, with higher and tighter armholes and trim sleeves. Then there's the two-button cuff that blends Jermyn Street with a dark corner in Berlin. And it's cut tight across the chest. At first I like it; I look good. But when I stretch my arms out to hail a cab—or put on my suit jacket—I notice the shirt pulling and gripping. The casual observer might think I was trying to effect my own Hulk homage moment. Great shirt, but more suited to nighttime, when, admittedly, the Hulk homage sometimes works.

FIT Very slim.
FOR Looking great in the office—and even better at night.
PRICE $305; 800-704-7317.

RALPH LAUREN

Ralph is everyone's favorite uncle—he never steers you wrong. His Purple Label shirt takes all the best elements of what American men want and mixes in just the right amount of British flair. Trim but not tight, and perfect under a suit. He also cuts it long so that it tucks in nicely, eliminating constant readjustment. (Others I tried were cut shorter in the body, and while that reduces bulk, it also means tails pop out much more often.) This is a shirt that makes a man feel confident and a woman take notice. And Ralph makes it all look so easy.

FIT British meets American—always a good union.
FOR Making any suit look more expensive than it is.
PRICE $265; 888-475-7674; www.polo.com.

CHARVET

Not just the shirt all men aspire to, this is the shirt all shirts aspire to be. Short of custom, nothing compares to a Charvet. Let's start with the fit: full and snug at the same time. When you're standing, it seems to mold to your body. Sitting, the shirt gives and becomes full. As I can best understand it, it's all in the cut—the body is longer and the base is split. There's also a squared-off bottom rather than the regular tails, and the pieces are notched, so there's ease of movement. Then, perfectly subtle French cuffs, neither bulky nor chunky; buttons that feel solid to the touch, like the door handle of a Bentley: all equally at home with your best suit or under a cashmere V neck. This is a shirt for the ages. I will hunt no more.

FIT Sublime.
FOR The rest of your life.
PRICE $300; available at Bergdorf Goodman for Men, 212-339-3308.