Probably one of the most common questions on the clothes discussion forums I read is “does this fit right?”

A typical sequence of answers goes like this (for the sake of your eyes, I’ve omitted the excessive use of smilies that infests all internet boards):

Poster A: Perfect! Looks great! Maybe just a bit more waist suppression!
Poster B: Looks like ass. Take it back and castrate the person who sold it to you.
Poster A: No, it’s just the style of that particular jacket.
Poster B: Nonsense.
Thread Starter: I thought I liked it, but now I’m more confused than ever. Does it look good or not?
Poster C: It’s not bad, but needs some work. I suggest you get it altered if you can, by a competent tailor (there then typically follows an extensive list of alterations required, many of which will cost more than the item is worth, or have dubious chances of success).
Poster B: It’s beyond repair.
Poster D: This is what you get when you buy ready-to-wear. The only solution is to double your budget and go made-to-measure. Or better, quadruple it and go bespoke. I highly recommend my own tailor X (this last sentence is usually to demonstrate to all other thread participants just how wealthy D is)
Poster A: You just don’t get where Thread Starter is coming from; you’re all being neurotic. It looks fine.

And so on, ad infinitum.

The depressing thing is that only rarely does someone point out the real problem: Thread Starter has absolutely no clue what he wants to look like.

Yes, there are some basic rules of fit. These are few in number, and more so if you allow for the fact that sometimes designers wish to deliberately subvert the conventional rules of fit in order to achieve a particular aesthetic effect. But even if you want to, say, get a conventionally-fitting suit, the number of basic rules is few and they tend to be tautological in nature (to get a conventionally-fitting suit, you have to follow the conventions of proper fit).

Beyond that, there is a far more interesting world of interpretation and personal preference, on the part of the designer/tailor and yourself, as well as any other intermediaries involved in the chain of manufacture and purchase ending with you being happy with the jacket on your back.

To competently navigate this world requires knowledge of what you actually want to look like.

Most people have a vague impression of the effect they wish to achieve (“I want to look cool/sexy/businesslike/like James Bond/whatever”) but nothing beyond that. This goes back to my article on style, where I used the example of Agnelli to point out that the man knew himself and exactly what impression he wished to create. Appropriate fit, as well as style, will vary depending on that desired impression.

To get to that stage requires educating and refining your own eye, and understanding your own personality and intention. It starts by actively observing the world around you. Passers-by, colleagues, friends, public figures, magazines, works of art, everything. Make a mental note of what looks good to you and then try to think what it is about the look that appeals. Then compare what you see in the mirror when you get dressed to that idealised image. It won’t match up. Some of that will be down to differences in physique and physiognomy, uncorrectable without either major lifestyle change or extensive cosmetic surgery. Personally, I dislike contemplating both of those options…

Think about what remains; those areas you can do something about. Think about the details that differ and then when you go shopping or go to your tailor, look critically at yourself in a mirror and make note of the bits you don’t like. If you’re shopping ready-to-wear and there are too many differences, shop around more until you find a brand that doesn’t have those deficits when you put it on. If you’re ordering a custom item, ask your tailor if anything can be done about those details. Oh, and don’t try to use lots of tailor-jargon. Just explain it in clear, simple, everyday English. Let them do the hard work of translating that into specific alterations; it’s their job and they will likely be better at it than you.

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