Well, hello there. Welcome back to our series on the menswear ‘rules’, where we explain why these conventions exist and as a result how they should be broken. 

The key is not to follow any rule blindly. Instead, see these rules as advice from a well-dressed friend, a well-informed and well-meaning one, but still one you might still happily ignore – because his style is not yours, or because you think he’s just wrong. 

So, socks should match your trousers, eh? Why’s that?

Because if you have mid-grey trousers and a mid-grey sock, ending in a nice elegant shoe, it extends the visual length of your leg. It makes the legs look longer and sort of makes you appear taller. 

It’s also elegant. If you’re dressing classically and smartly, you don’t want high contrast in the sock area. You want subtlety and understatement, and nothing is subtler or more understated than a matching sock and trouser. 

This involves having more colours of socks than just black or navy, so as I wrote years ago, in some ways socks are a good indication of whether you care. And the rule presumes you’re wearing long socks, which as I wrote more recently is only really needed for these kind of smart outfits.  

So you get the look right? Now here are the exceptions.

One. Matching socks and trousers is a smart look but can be a little boring. A coloured sock that harmonises nicely with the rest of the outfit is almost as smart and can be more interesting. 

So a navy suit is lovely with a purple sock, for example, as is a grey suit with forest green. (Above, myself and Bruce Boyer with green and purple options under grey trousers. Of course, colour is more at home with sports jackets like Bruce’s, rather than suits.)

Brown and green suits open up more colour options, and brown tweed is especially nice with rusty orange. These are not my personal style – I’ve worn them in the past, I’ve enjoyed them, but today I prefer something subtler. If I had a friend that dressed like that I’d certainly admire him – I’d take a real, visual pleasure in it – but I wouldn’t dress like him. 

Two. You might be really tall and not want to appear taller. In that case consider breaking up those long lines instead – with turn-ups, belts, and differently coloured socks. 

There’s a little on this point about flattering body shapes in the Guide to Suit Style, though I know we should write more on it.

Three. You might not want to appear that smart. This is probably the biggest caveat, and certainly a reason not to always wear long socks in fine, delicate materials. 

But at the same time, I still wear navy socks with my jeans because it looks nicer than black. Indeed, with mid-blue jeans I particularly like grey socks, because there’s less contrast and grey goes with everything. I also wear charcoal casual socks a lot for the same reason (see above). It’s still worth thinking about socks even if the outlook is casual. 

Four. Pale trousers don’t always look great with matching socks. Pale socks are a little showy, perhaps a little effeminate, and that’s not what everyone wants. 

The solution is to go for the same colour, just a tone or two darker. I have taupe and dark-taupe socks from the Anderson & Sheppard that are particularly useful for this. I also really like the dark-taupe colour as a more interesting partner for grey or charcoal trousers (above). 

Five. Just style. OK this is actually the biggest caveat. Matching socks may not be your style, and you might have strong opinions on colours and combinations that are. 

Like a white sports sock with chinos that you think has nice Ivy connotations, for example. Points of physical flattery, like leg-lengthening, are less important than style.

More advice from that well-informed, well-intentioned friend here, in the Rules section of PS.

If you want to browse a big range of trouser/sock combinations, by the way, there’s no better place than the Mes Chaussettes Rouges site – click into the knee high, cotton category and see dozens of options. Not all of which I would wear, but some great inspiration in there nonetheless.

Let us know what sock and trouser combinations you particularly like. As if you needed the encouragement.