A lot of the old school tailors operating in the west end of London wear cream silk handkerchiefs in their breast pocket. This is rather contra to the consensus that linen or cotton is best with a business suit, as the matte surface contrasts with the smooth texture of a silk necktie.
I am part of that consensus in one respect: I don’t like cream silk handkerchiefs, they always look a little louche. But I disagree in another, more important respect: this is a rule that needs to be understood to be applied, and balance isn’t necessarily always achieved with a linen square.
Assuming you don’t wear silk shirts, there are three factors at play here: suit, tie and handkerchief. Contrasting their textures is certainly the aim for a sophisticated ensemble. But there is a lot of variation is suits. Modern worsteds are often very smooth, even shiny, and flannel is closer to many current tweeds in texture. It is often recommended that one wear a silk handkerchief with tweed, to contrast with the rough cloth. So the argument applies to some extent to flannel. Plus, a tweed jacket will often be worn with a woollen or at least knitted tie. The argument this time is one of harmonisation with the suit rather than contrast.
In an outfit one needs to balance both harmony and contrast, in texture in the same way as pattern. A worsted suit, silk tie and linen handkerchief are certainly a good example of that. So are a tweed suit, woollen tie and silk handkerchief. But on texture alone there’s no reason you can’t swap the accessories between those two suits.
The other consideration, of course, is formality. A linen hankie and tweed suit might both be of relatively rough cloth, but the former is a lot more formal than the latter. This is the reason that the worsted combination above is the most common for business dress. Equally, a silk hankie and silk tie are both smooth, but apart in suggestions of formality. Hence why silk and wool with a tweed suit are usually worn in a hankie and tie respectively.
However, if you are not a lawyer or a banker – or for other reasons are more interested in experimenting with your dress while retaining intelligence in your ensembles – formality can be de-prioritised. A cashmere tie with a worsted suit can be a lovely combination. And I would argue it can just as well be worn with a silk hankie as a linen one. The former creates greater contrast.
Of course not all men today like to wear a tie, and a handkerchief can be a nice way to accessories while being open-necked. In that case, a silk handkerchief is just as valid as linen. Contrast with the texture of the suit perhaps. Or take into consideration other parts of the outfit – if you want to wear suede shoes, pair them with a silk handkerchief to get that contrast.
Whatever you’re wearing, just remember to consider both texture and formality. And avoid cream silk hankies.