In the world of tailoring, much like in any specialised field, there’s a certain level of insider knowledge. Reputations travel and people who work in the rag trade are often in the best position to know who’s doing good work. If you’re searching for a reliable tailor and have yet to find one, a good strategy is to ask recommendations from several high-end clothing stores, particularly those selling premium suits, as they typically require more intricate alterations. (Or, if you live in the UK, you could look into MR PORTER’s FIT & FIX service, which pairs you with a tailoring expert in your local area.) Even stores with in-house tailors usually know other reputable tradespeople in the vicinity. A name that emerges repeatedly in your inquiries is likely a tailor with an excellent reputation.

When working with a new tailor, start with a simple task. Instead of having them overhaul an expensive suit jacket, opt for a less costly item and a less complicated adjustment such as hemming a pair of chinos or customising a shirt. Once you receive the altered item, scrutinise the workmanship. Check if it fits correctly and whether the sewing is neat and meticulous. As your trust in the tailor grows, you can gradually entrust them with more complex and valuable pieces.

Effective communication with your tailor is crucial. It’s important to clearly convey your expectations and desired outcome, but avoid over-directing their work. A competent tailor won't require step-by-step guidance on how to execute their job, and a less skilled one isn’t likely to improve with detailed directives from someone who doesn’t even know how to sew. Instead, convey your visual goals, using photographs to illustrate the look you want, and allow the tailor to devise the best technical solutions. Overly precise instructions can sometimes lead to suboptimal results, so it’s best to trust your tailor’s skills and judgement.

Almost anything from T-shirts to overcoats can be tailored, but much depends on the garment’s material, construction, and detailing.

Material: while a general alterations tailor can manage a wide range of tasks, some items require a specialist's touch. Knitwear, for example, requires a knitwear specialist; leather items require someone who has the right equipment to sew through the thicker material. When deciding whether something can be altered, make sure you’re using someone who has worked with that kind of item before.

Construction: the simpler the garment, the easier it is to tailor. T-shirts, for example, can be almost entirely recut. But a suit jacket or sport coat will be made from many layers of haircloth, canvas, and padding, which are sewn together using specialised techniques such as pad stitching. When shopping for a suit or sport coat, make sure the jacket fits well across the shoulders and around the chest, as these areas will be harder to alter.

Similarly, if you find something that fits a little too snug in some areas, peer inside the garment and look for something called “seam allowance”. This is tailoring terminology for the excess material left at the seams. Higher-end garments, though pricier, often have more seam allowance, providing flexibility for future size adjustments. This may be useful down the line if you gain weight.

Detailing: finally, when considering off-the-rack items for alteration, be mindful of design elements such as zippers, ribbing and pockets, which may limit alteration possibilities. Unique linings or unconventional panel cuts also add complexity.

Tip: when deciding what to tailor, consider pinning the garment to see how it might look post-operation. For example, if you’re unsure whether you should shorten an overcoat (a relatively easy job), pin the hem up so you can visualise the effect.

Although a tailor can do almost anything, you probably want to avoid total reconstructive surgery, as major jobs come with higher tailoring bills and some risk. Think of it as akin to purchasing a car. You could theoretically transform a sedan into a convertible, but it’s more cost-effective and simpler to buy a convertible outright. The fewer and less complex the alterations, the better.

As a general rule of thumb, it’s easier to alter the bottom half of a garment than the top. Hemming trousers or tapering them from the knee down is straightforward, but adjusting the hips or thighs can be more complex due to constraints such as back pockets. Similarly, you can easily shorten the sleeves on a dress shirt or nip the waist, but it’s more challenging to change the armhole, shoulders and chest.

Additionally, it’s always easier to take something in than let it out. If you are having difficulty finding clothes that fit well off-the-rack, fit the largest area of your body and see if a tailor can trim the other areas down. For instance, if you have large thighs and a prominent backside, find trousers that fit these areas comfortably first. Limiting your alterations to the easier areas, and making sure your tailor is only having to take things in, will make sure you’re not knocked over by the tailoring bill in the end.

Sometimes, trying on a different size or garment model is easier than trying to alter one that doesn’t fit. If you try on trousers and see the side pockets flaring out like a charging elephant’s ears, the trousers might be too tight around the hips. While a tailor could probably adjust this by letting out the hips, a more straightforward solution might be to just get a larger size. Similarly, if you try on a suit jacket and see divots on the upper sleeves, the jacket might be too tight across the upper back. A tailor can rectify this by letting out the centre back seam, but this could lead to misaligned stripes or plaids in patterned fabrics (ugly, but not as ugly as divots). Again, trying a larger size or a different jacket model might be the simpler choice.

Many of us have items in our closets that no longer fit quite right, especially those ultra-slim garments from a decade ago that seem to have shrunk over time. A tailor’s role isn’t limited to adjusting new acquisitions; they can also breathe new life into existing wardrobe pieces. So, what to do about those excessively slim outfits?

For a tailored jacket, like a suit jacket or sport coat, there’s typically about an inch of leeway to expand the body using seam allowances at the sides and back. If the armhole feels restrictive or tight at the front, a half-inch adjustment might be possible, though this depends on the construction of the sleeve head and armhole, as they are interrelated. High-quality trousers often have ample fabric at the waist to allow for letting out, but the legs might only accommodate an expansion of half to three-quarters of an inch. Beyond these, your options are limited. Shirts that are too tight are generally beyond help. Similarly, tight shoulders or sleeves on a suit jacket are usually irreparable, and if the seat of your trousers is snug, little can be done.

Ultimately, looking good in clothes is about cultivating an eye for detail, identifying your unique fit challenges and finding a tailor who can help you make the necessary adjustments. Not everything has to go to a tailor – the trend towards looser, fuller clothing over the past few years is mercifully more forgiving than the slim-fit era of the early 2000s. But it helps to know what a tailor can do for you and how to use their services best.