My relationships with my tailors over the years have proved to be slightly exaggerated reflections of my romantic life. There was that post-collegiate fling with a temperamental Neapolitan that ended in a costly parting; a friends-with-benefits situation involving a buddy’s fledgling bespoke service that lasted for just one blue blazer; a Beverly Hills I-just-can’t-quit-this-fling with a showbiz icon. Finally, I settled into a mature, drama-free relationship with a Savile Row tailor almost two decades ago. I have not looked back.

Mastering the world of custom-made things can be an expensive education. Decisions are myriad, and it requires a certain type of imagination to be able to picture how the final result will look. It is one thing to try on a mass-produced and finished suit and know whether it works for you. It is another to make a leap of faith. So, in the interest of making the neophyte feel comfortable, we’ve put together a few rules of the road on how best to emerge from the chrysalis of bespoke as a resplendent, worsted butterfly.

Most great tailors can work in more than one style, but some of the more established ones have developed house styles over the years. Like the brushstrokes of Old Masters, these signatures, such as the way the Attolini family of tailors produce a jacket with a roped shoulder (ie, a slightly raised bump where the sleeve meets the body of the suit), are not for everyone. A broad-framed, athletic man might prefer a more natural-shouldered coat similar to what Mr Anthony Sinclair designed for Mr Sean Connery in the early Bond films.

So before you set up an initial consultation with a new tailor, see how his style and yours match up. If you want to look like an insouciant Italian industrialist checking into Hotel Il Pellicano, don’t visit a Savile Row tailor who has been dressing Coldstream Guards since the Crimean War. “You don’t want to go to a sushi chef and ask him to cook you a hamburger,” says Mr Thom Whiddett, who came of age in the back rooms of London’s best tailors before partnering with Mr Luke Sweeney to form Thom Sweeney, a house that offers traditionally constructed suits with a modern twist.

When you arrive for your first appointment with your tailor (sometimes called a consultation), there will be a number of decisions that you will have to make. So have a think about what you like and when you will be wearing the suit. Ask yourself: do I prefer a suit with a single- or double-buttoned front? Will this suit be for the hottest summer days or are you after what is known as a three-season (autumn, winter, spring) weight? How about the trouser width? Even as the fashion pendulum is swinging to a slouchier look, do you prefer to cling to your skinny-legged, Mod roots? To make sure your initial consultation goes well, consider bringing an inspirational image with you. (MR PORTER’s Style Icons page is a great place to start.)

“One of the first things that we ask a new customer is what he likes (or does not like) about suits that he already owns,” says Mr Whiddett. “In general, we come across two types of client: those who have definite opinions and those who leave it to you. My job is to steer you in the right direction.”

There are certain topics that a client can (and should) assert himself on, such as the length of a jacket, but then there are topics that he should defer to his tailor on; fabric being one of them. It is hard for most of us to visualise how a piece of material not much larger than an iPhone will look and feel when it is covering our entire body. You’ll hear tailors talk about how a particular fabric will “make up”, meaning how it will look when the suit is finished. Listen to them, because each fabric has its own properties. A flannel, for instance, may look loungey, while a woollen fabric made from a high-twist yarn will not crease easily and would be ideal for a crisp-looking travel suit.

One of the first decisions that you’ll have to make is what pattern of fabric you’re after. Start with simple blue and grey suits – ones in which the subtle tailoring, rather than the baroque patterns, are what catches the eye. Even if one aspires to dress like Mr Lapo Elkann, it is important to remember that his arsenal probably exceeds 100 suits, while yours is (probably) smaller. “If you have a bold-check suit, it very quickly becomes a signature look of yours and everyone knows that suit,” notes Mr Whiddett. “But a plain navy is more versatile.” A good benchmark for a well-tailored suit is not someone saying, “Great pinstripe!” but rather, “Have you been on holiday? Cut your hair? New personal trainer? What’s different with you?”

If you’re working with a proper tailor, you should have at least two fittings before you receive your finished suit. During the first fitting (often called “the basted fitting”), you’ll find yourself wearing a rough draft of your suit that is only loosely stitched together. This is the moment to say things such as, “In the winter, I tend to pile on a few pounds. Could you leave me a little room in the seat?” If the jacket is tight in the shoulders, the jacket will not fix itself over time. Tell your tailor, and together you should be able to reason out a compromise where you give up a little bit of the slender silhouette in exchange for the ability to, say, raise your arm to hail a cab.

The second fitting is more about getting the details – such as trouser and sleeve length – right. There’s no bigger drag in bespoke than ending up with a suit that isn’t comfortable to wear. You won’t wear it, and that’s money down the drain. A good tailor should be able to deliver a suit that looks and feelsgreat.

Over time, you and your tailor should develop the same shorthand that you enjoy with a trusted colleague. I have worked with my tailor, Mr Stuart Lamprell, for more than 15 years. When he is in New York, I have him round to my club for a game of squash and a pint. Many suits into our partnership, we know each another well – well enough that he put a dark-green lining into one of my blue suits because it reminded him of the leather couches in my club’s locker room. He knows that I love rules – grammatical and sartorial – so if the tie that I wear with my tuxedo is grosgrain, so should the facing on the lapels of my tuxedo jacket be. He is also quite good at saving me from myself.

Swept up by the “statement topcoat” trend we all saw coming at last winter’s men’s shows, I approached him in spring about working on something that would have been a tragic amalgam of Joseph’s Amazing Technicolor Dreamcoat and Withnail’s 19th-century riding coat. As I held up a series of green-and-red tweed swatches one morning in his shop on Sackville Street and prattled on about the raglan sleeve, he said, “Well, that’s a look.” The point was well-taken. I tend to lunch with writers, photographers, designers and web developers. I am not often asked to portray Nicely-Nicely Johnson, the aggressively attired gambler from Guys and Dolls. My old covert coat would do for another season.

Like many professions, tailors have their own argot. For example, always say, “coat” because “only potatoes have jackets,” as the Savile Row Bespoke Association helpfully points out on its website. Here are some other terms one may encounter during a fitting.

• Balance

The balance refers to the relationship between the length of a jacket at the front and the length at the back. These ought to look the same. 

• Basting

The loose stitch used to assemble a garment for a first fitting. Don’t be shocked if your tailor whips out a small knife and removes your coat sleeves while you’re still inside it.

• Button Stance

Where the buttons on the front of a coat sit.

• Lapel (Notch vs Peak)

The lapel is the fold of fabric on the front of a coat that runs from the collar to the buttons. On a suit coat, the two most common styles of lapel are a notch and a peak. The former features a notch where the collar meets the lapel. The latter is more of a statement with the edges pointing upward towards the shoulder.

• Kissing Buttons

Most bespoke suit coats have “working buttons” – or buttons that open. A mark of precision on a bespoke suit coat is having three or four sleeve buttons that just touch and overlap on the edges. These are often called “kissing” or “waterfall” buttons.

• On The Cod

Savile Row slang for being at the pub.

• Patch Pocket

Lacking a flap or closure, this feature is considered a more casual look appropriate for a blazer or a summer-weight suit.

• Pattern

This is the blueprint, sketched on a man-sized piece of paper that reflects not just a client’s measurements, but also how he stands and any other physical quirks. Some tailors start with a standard outline for, say, a 40 regular coat and then personalise, while others employ…

• Rock of Eye

A form of artistry possessed by the finest tailors. This is the ability to cut a pattern freehand, using only a tape measure and some chalk as a guide.

• Slash Pocket

A pocket that slashes on a coat’s diagonal as opposed to sitting on a more traditional horizontal.

• Ticket Pocket

This is the smaller pocket above a coat’s regular pocket. It is called a ticket pocket because it is designed to hold… well, you guessed it. A handy place to keep one’s Oyster or Metrocard.