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If styled right, a cap is a wonderfully useful accessory.

Not as formal as a fedora, yet not as casual as a beanie, it can bridge a greater range of outfits than any other hat.

When the temperature is in single figures, and your lack of hair makes a hat a necessity, this makes a good cap extremely valuable.

But as with many hats, they require some thought as to shape, proportion and colour in order to suit the wearer.

suede-eight-piece-cap

The basics are similar to buying a good fedora or trilby: you want something that echoes the proportions of your face (and to an extent your overall body shape).

So if you have a large, round face, you need a larger, rounder cap.

Of course, caps don’t have the same number of permutations as a hat - brim width, crown height, crown taper. But the way the body of the cap is cut makes a surprisingly big difference.

For example, I always used to think that eight-piece caps, as I’m wearing here, were too big and floppy for me.

The vast majority are, but they don’t have to be. You can still make an eight-piece model that is relatively trim, it’s just that most aren’t made that way.

I happened to try this cap at Lock & Co last year (the Indie suede model) and noted that it suited my face better than most - particularly with the brim enthusiastically bent and rounded.

Unfortunately, they had just sold out of my size (59) so it wasn’t until last month that I was able to buy one. They also made it in a slightly darker shade of suede this year, which is much more versatile.

how-to-wear-a-cap-with-tailoring2

The other cap I have is a navy Wigens cashmere model from Trunk. The fact it’s dark makes it more versatile than the suede, and it’s Storm System-treated which makes it a lot better in the rain.

It is a classic flat-cap style, made with a single piece to the body. And yet the proportions are very similar to the Lock & Co eight-piece: rounded around the top of my head, but not flopping over to one side or the other.

I find the other Wigens caps too narrow and small in the head for me, so it’s not even a case of a particular brand being of one type - just the model.

suede-cap-lock-co

As mentioned, body shape is also somewhat relevant.

A larger or taller man will find it easier to wear a larger hat of any sort; smaller or shorter men may be better with something neater. But consider face shape first.

In terms of style, anything that makes a cap seem more personal and worn-in will help - like that rounded brim.

And try to keep the formality of the outfit roughly in line with the cap. A hairy Harris tweed is not going to work with a worsted suit.

Finally, I would say that as with much of what we discuss on Permanent Style, this is how to master the basics: how to dress subtle, simply and elegantly.

A short man with a thin face can look great in a big, floppy newsboy cap. But it will be a question of fashion and character.

If he’s still wearing that style in five years, credit to him. But it’s unlikely.

how-to-wear-a-green-scarf

Elsewhere in this outfit:

  • Cashmere overcoat by Cifonelli tailors, Paris. (Perhaps my favourite ever bespoke piece.)
  • Green cashmere scarf by Loro Piana.
  • Cream trousers in super-heavy wool by Elia Caliendo (from the Holland & Sherry Pardessus bunch)
  • Suede chukka boots by Saint Crispin’s. (More on those separately.)
  • Peccary gloves from Lavabre Cadet.

Photography: Jamie Ferguson @jkf_man