Style Guide|Men’s Designer Hats|What to wear if you have a square face shape

By Clara

Have you ever wondered about how your face shape can affect your choice of hat? What are the most flattering designs if your face shape is square or square-ish?

Here are a few suggestions from Karen Henriksen - expert milliner and designer of distinctive hats for men since 2009.

(If you’re not sure what your face shape is, take a look at this post for some helpful tips.)

Square face shapes : some examples

Karen has picked out sportsmen and celebrities to highlight characteristics of the square face shape. A pronounced jawline is quite typical of the square face shape.

Cricketer Alastair Cook.

Cricketer Alastair Cook.

Footballer Harry Maguire’s face shape could be described as heart-shape square.

Footballer Harry Maguire’s face shape could be described as heart-shape square.

Actor Brad Pitt, whose face shape could be described as long square.

Actor Brad Pitt, whose face shape could be described as long square.

Formula 1 star David Coulthard, his face shape a perfect square in our opinion!

Formula 1 star David Coulthard, his face shape a perfect square in our opinion!

In particular Brad Pitt and Harry Maguire have mid-length hair styles. These hairstyles help to soften the overall outline of their face. A very short haircut would be unflattering - by making their face look even squarer.

Similarly with headwear, you should consider hats that add a rounder, softer shape, and perhaps some asymmetry too. Here are a few examples of hat shapes that would work well for you if you have a square or square-ish face shape.

Distinctive hat designs for square face shapes

  1. Flat caps

Some flat caps of note are the more rounded designs in Karen’s extensive range. Here are our handpicked designer hats for square face shapes.

The ever-popular deep fitting Clive flat cap with its rounded outline.

The ever-popular deep fitting Clive flat cap with its rounded outline.

Bingley flat cap with pleats at the back adding a little width.

Bingley flat cap with pleats at the back adding a little width.

A new design in the range, the Skipton also features pleats and a little asymmetry.

A new design in the range, the Skipton also features pleats and a little asymmetry.

2. Beret-caps and baker boy style caps

With their rounded and softer feel beret-caps and baker boy style caps can be really flattering for men with squarer face shapes. Add a little asymmetry by wearing one of these tipped to one side.

The generously shaped Assa beret-cap in soft grey pure wool.

The generously shaped Assa beret-cap in soft grey pure wool.

Perry is a baker boy-style cap, with a rounded feel and a short peak. A flattering design suited to square face shapes.

Perry is a baker boy-style cap, with a rounded feel and a short peak. A flattering design suited to square face shapes.

Gower beret-cap, a fine hybrid of beret and cap, in a soft grey denim.

Gower beret-cap, a fine hybrid of beret and cap, in a soft grey denim.

Hector, a trilby hat with a softer crown and a little asymmetry in the design.

Hector, a trilby hat with a softer crown and a little asymmetry in the design.

3. Trilby hats

Finally if you’re into trilby hats, have a look in particular at brimmed hat designs with an asymmetric style, or worn slightly tipped. Hector would be a great hat for square face shapes, as the crown has a softer outline and has a little asymmetry.

Have a try and see for yourself

I hope you found these tips useful. The best way to see what fits is still to have a feel, try a design on and see how you like it in the flesh.

All our hats, flat caps and beret-caps are made in-house, in the London studio by Karen herself. Everything is made to order and to size, to ensure the perfect fit. All online orders can be returned for a refund or exchange.