Dear Style Shrink,
I’ve got an anvil-shaped head, which makes it very difficult to wear hats. But I also have very little hair, which means that I have no option but to reach for some insulating headwear when the weather gets less favourable. What would you recommend I go for? Anon, Mill Hill
In your case I would suggest opting for something a little more architectural, which creates the illusion of an elegant head shape but also keeps you warm. London-based hatter Lock & Co does an excellent line in cashmere engineer caps, which are constructed by stitching a top panel to a head wrap, helping to create a less lumpen, more angular shape.
Cashmere cap by Lock & Co Hatters, $252 at lockhatters.co.uk
When it’s really cold, however, you could do worse than opt for an oversized nylon trapper hat, which will draw attention away from that head before you can say, “Fashion!”
For those with rounder heads a beanie can work quite nicely, providing it’s made from chunky cashmere in a statement hue and it hugs the shape of your head without sagging.
Cashmere beanie by Loro Piana, $465 at loropiana.com
Longer face shapes would do well to consider something that creates a sense of balance. A well-considered felt fedora could work well, so long as it aligns with your personal style (a fedora looks great with tailoring, not so much with sportswear).
Fedora by Saint Laurent, $781 at matchesfashion.com
If you’ve got a square face, the hats that tend to look best are those with a wider brim, as demonstrated by Taron Egerton, who regularly wears one in that style. The best to go for, in my opinion, are those in darker shades, however, so not to draw too much attention. Hats can be divisive, after all.
Fedora by Nick Fouque, $1471 at matchesfashion.com
And if you’re Michael Stipe, one of these goatskin skull caps should probably do the trick.