I found it hard to feel good in a hat because of my very short hair and specs. To my eye, hats look better when hair is peeking out from the bottom of the hat, and you don’t have eyewear competing and getting in the way of the silhouette. So yes, I was on Team Hat Averse. 

Yet I need to wear a Winter hat daily in cold weather for dog walking, or when I’m out and about for longer periods of time. It’s AMAZING how effectively an ear-covering hat can reduce earache. So I’ve done lots of hat experimentation to come up with a style that’s fairly flop proof and makes me feel fab. 

Choose a Beret

It’s not the beanie, cloche, fedora or newsboy that looks great on everyone — it’s the beret. Do yourself a favour and try one if you haven’t done so already. They come in an assortment of styles. There’s the classic, dressy and more rigid felted wool version that I’m wearing below, and all sorts of relaxed and floppy knitted silhouettes. I wear both. The collection provides a wide range of examples.

Choose a Low-Contrast Colour

I’ve found that choosing a colour that is low contrast to the colour of your hair works well for two reasons. It creates a more subtle visual effect, which works well when you wear specs or don’t want the hat to stand out in the outfit. A self-colour hat also matches every outfit because it looks like an extension of your hair. Versatile, simple and unobtrusive. 

I have platinum blonde hair, which makes cream, white and tan hats my low-contrast hat colour. Choose any dark colour beret for dark hair, and mid tones when you have medium dark hair. There is no need to stick to neutrals, although they will have the most subtle effect. 

And last, I have a small head, which makes most adult hats a bad fit. Children’s hats fit a whole lot better, and if you look long enough, you’ll find a few sophisticated silhouettes.