This is only my personal preference, but I frown on pinstripes for anything important. Depending on your looks, I think they tend to scream “gangster.” I’m all about solids. Navy blue, charcoal, or black.
Here’s what I’ve heard:
Belt color should always equal shoe color.
Socks can match shoes OR pants.
No, that would look silly. Loose the colored socks and stick with black.
I will agree that pronounced pinstripes does look a bit 1920s gangster. I prefer a more subtle pattern.
Pinstripes = gangster? That’s a shame… I really like the pinstripe. What other patterns are there?
I suppose a subtle herringbone is an option, or tweed…but again…solids for important stuff.
Pinstripes can be fun for dressy cocktail parties or other non-career stuff. I just don’t like them for business. I’m sure there are hundreds of Dopers who’ll disagree.
You forgot to mention the squirting flower, the bulbus red nose, and the ol’ arrow through the head doohickie. 
But seriously, black really isn’t a good suit color. Save it for formalwear.
The Flying Dutchman, I don’t know your location or budget, but here are some rantings from a U.S. perspective on a $1000 budget:
The Suit Itself:
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100% wool is The Rule of Thumb. 3% Lycra for stretch is fine, but you may not feel the difference. Polyester is verboten.
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You can’t go wrong with Navy. Charcoal and gray are also versatile. Earth tones (brown and such) may be too casual. Black is creepy, traditionally a color for funerals or tuxedos. The Secret Service Look scares people
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Fit is everything. Have someone measure you, then try on coats in that size as well as coats that are a size smaller and larger. Know how a good fit feels and looks like. A good suit should feel like a second skin while making us look good.
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Two-button or three-button? It’s all a matter of taste. Generally speaking, three-buttons look better on taller people. There are always exceptions, though. Forget four buttons or more.
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Double-breasted suits only look good on certain types. If you want double-breasted, try one on and ask for second or third opinions.
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Alterations, alterations, alterations! Ravenman’s input is right on target. An experienced tailor can transform a regular suit into one that looks like it was designed just for you. Tailors are like mechanics or barbers; once you find one you can trust, you won’t feel comfortable going to anyone else. I buy suits from Macy’s and have them altered at Joseph Banks because the tailor at JB does excellent alterations. You may have to pay a surcharge, but it’s worth it.
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Pleats or no pleats on pants? The general rule: short or skinny=no pleats; tall or wide=pleats. There can be exceptions. Try both types and compare. msmith537 already mentioned this, but it bears repeating: if it has pleats, have it cuffed (1.5 inches is the standard, but you may want more or less depending on your height); if it has no pleats (plain-front), have it hemmed with plain-bottoms (no cuffs). Suit trousers come unhemmed, so it’s a good idea to burn these rules into your long-term memory. Salespeople may mix this up, which means you end up with the Tres Tacky Look.
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Stripes do scream gangsta (or banking executive/loan shark). If you insist, go with pinstripes (the thin kind) in a color that almost blends in with the suit. For instance, this multistripe from Men’s Wearhouse looks like solid charcoal from a distance. You can try herringbone or windowpane (the more subtle the better) suits for texture.
The Outfit as a Whole: As other Dopers noted, a coat and jacket is just part of the suit deal thingy. You’re actually wearing a uniform consisting of other complementing parts that need just as much attention. I know this may seem like a lot of work, but the good part is that quality clothing never goes out of style. So, from top to bottom: -
Shirt: 100% wrinkle-free cotton is best. Men’s Wearhouse, Joseph Banks, Brooks Brothers, Paul Fredrick, and Nordstrom all carry them ($50 to $100+). A cotton-polyester blend shirt is also wrinkle-free, but it doesn’t feel the same. (If you must get a blend, the polyester content must be at least 40% for effective wrinkle-resistance.) White is a good safe choice, but blue (almost lilac) is more sophisticated. Avoid button-down collars and opt for straight, spread, or cut-away. French cuffs are very cool and don’t that much more. Like suits, your shirts should be altered if necessary for a proper fitting. The shirt sleeve should break at your wrist and show through your coat sleeves about half an inch. The collar should be loose enough to slip one or two fingers between your neck and the shirt. Note that cotton shirts will shrink after the first wash (about 3/8 of an inch).
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Tie: Silk is best. A number of makers now treat the silk to resist stains. Make sure the tie, after being knotted, is long enough to reach your belt buckle.
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Pocket square (handkerchief): If you’re going all out, get a pocket square to put in your coat pocket. The square can match either the color of your shirt or tie. If you want to get fancy, get two squares of different colors that match your tie (most ties come in at least two colors), and twist them so they form a swirl when you put them in your coat pocket.
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Belt: Leather is best. Match it with your shoes. This is a must. Some suits come with beltless pants. In that case, no worries.
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Socks: Should either match the shoes or pants.
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Shoes: Again, leather is best. You can never go wrong with black. Brown is more creative, but I’ve seen flame wars over whether brown goes well with a navy or black suit. If you decide on brown, darker is better.
Miscellaneous stuff:
The neat thing about suits is that you can create different combinations by wearing the same coat and pants (the most expensive pieces) with different shirts, ties, belts, and shoes. The Men’s Wearhouse claims you can get a week’s worth of different looks with 1 suit + 2 shirts + 3 ties + 1 belt + 1 pair of shoes within a $500 budget.
I’ve visited the Men’s Wearhouse site many times, which is why I’m using it for examples. Caveat: the MW suits on the dirt-bottom end (the cheapest) is mostly garbage. I’m more of a Joseph Bank guy, and I’ve had no problems with their Business Express line ($200-$300). Brooks Brothers is pricier, but they practically defined the American Suit look, so you can’t go wrong with them.
Here’s a link to buying a suit on a budget. This is from a European perspective by Thomas Mahon, the Saville Row tailor famous for his English Cut website. Of course, if you have the thousands of pounds/euros/dollars to afford bespoke, then go for it. There’s nothing like wearing something made just for you!
Noted, but disagreed with.
I have a nice 3-piece Pierre Cardin light grey that I wear with light brown shoes and belt. It is a great combination and I have received compliments from the ladies on it. Now, I have a charcoal grey that is verbotten to wear brown with, so it does matter on the shade.
As for matching the socks, it does work if you do it correctly. I have many black socks that have a simple red or blue pattern of some sort that works well with similar ties. Flair was the opperative word in that sentence, btw. Actually, matching socks to suspenders for the portly types is a great combo too.
-Tcat
It makes much more sense to buy a good quality suit (check the material, Italian and British woolens are the best), and have it professionally altered (by a good tailor). You will get a perfectly fitted suit for a fraction of the cost of custom-made. And beware the "Hong Kong Tailors’ who set up shop at your local Holiday Inn-you are getting a cheap quality suit, with questionable tailoring.
I picked up a wrinkle-free cotton shirt for my dad the other day at Carson’s for $30. It was a reognizable big name brand but I’ll be damned if I can remember who it was. Is Carson Pirie Scott a national department store or is that just a Chicago thing?
BTW - what is it with y’all against black? Is this a euro-thang that I am part of? Black is the new black here. I’d say 75% of the suits I see are black - I’m one of the few guys in the room with tan, taupe or grey. Navy is OK, but it is so conservative…which is fine, but certainly not my style. I have a navy sport coat in my office with a couple ties tucked in the pockets for dress-down days that turn up a meeting, but that is all.
And white shirts are fine, but again, yawn. We got all types of bold shirts here - stripes, paterns, colors, shiny fabrics, etc. There are some pretty neat shirts for tuxes that are white in the body, but the arms and back can be outrageous - florals, paislys(sp?), colors. Definitely a slavic tradition, but cool.
The one suit that I am so glad is dead here (thank og), is the purple suit. You can occasionally see one on some old commie minister, but mostly they are dead. But sheesh, talk about ugly. Trying to carry on a conversation with someone dressed like that is painful.
-Tcat
Some good advice so far. I wear suits just about every day at work (only occasionally sportcoats). I’ve always been pleased with my Nordstroms, Jos. Bank and Lands’ End suits. I just bought a suit from Chas. Tyrwhit, a London tailor, that is terrific.
I used to have an anti-pinstripe bias, but have learned that pinstripes need not leave you looking like a gangster. Dark gray or navy with a subtle white chalkstripe looks great, IMHO. If you’re just going to get one suit, though, I agree it would be better to get solid navy blue or a dark gray. More classic look, and more flexibility in choosing shirts and ties.
Some of my “rules” for business wear:
- sock color should match or closely compliment pants color
- watchband, belt and shoes should all be the same color, or very close to it
- don’t wear a striped tie with either a striped suit or a striped shirt
- a patterned or striped tie should be worn with a solid-color shirt
- there’s no such thing as a short-sleeved dress shirt. Wear a long-sleeved dress shirt and roll up your sleeves if you need to
- wear bow ties sparingly. I like 'em, but too many people make all the wrong assumptions about them
- a crisp white shirt gives you the greatest flexibility in choosing your suit and tie
If you buy a suit unhemmed, get it dry-cleaned before you have it hemmed or tailored for a more exact fit. There may be some shrinkage during the cleaning, and you’ll then be assured that your suit is just the size it’s going to remain.
I concur. Both Ivylad and Ivyboy have gotten suits as Men’s Wearhouse, and the service and attention to detail are superb.
Look for a high wool content and a little polyester mixed in. Not only will this wrinkle less, the poly component will help keep the moths away. That’s important in a suit that that’s going to hang in the back of your closet for most of the year.