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

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?

(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 created these sketches of some famous faces to highlight characteristics of the square face shape. A pronounced jawline is quite typical of the square face shape. As you can see, Brad Pitt’s face is not as obviously square as the others, but could simply be described as angular. Angular face shapes will suit many styles, but hats with a softer outline will often be the most flattering.

Cricketer Alastair Cooke

Formula 1 Driver David Coulthard

Footballer Harry Maguire

Actor Brad Pitt

Slightly longer hairstyles can help to soften the overall outline of the face. A very short haircut tends to emphasise a square face shape.

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 angular 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 and angular face shapes.

The Gregory flat cap has a round outline, with shallow fit at the front and depth at the back.

The popular deep fitting Clive flat cap suits many different face shapes, including angular ones.

The Selby flat cap has become a bestseller, with its close-fitting design. The back features two small darts which give a little squareness, but the front is quite rounded.

The Jake style has quite a traditional look, and will suit most face shapes but particularly more angular ones.

The Casey design has a rounded outline with a small pleat at each side.

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

2. Beret-caps and baker boy style caps

With their rounded and softer feel beret-caps and baker boy or newsboy 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.

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

The Jack newsboy style - although the shape has a certain squareness, the outline is softened by the fabric. This design will suit angular faces, although perhaps not the more pronounced square faces.

Gower beret-cap, a fine hybrid of beret and cap, with an unusual but flattering asymmetry..

The generously proportioned Assa beret-cap is great for square and angular faces.

3. Trilby hats

Finally if you’re into trilby hats, have a look at brimmed hats with an asymmetric style, or with a little shaping in the crown.

The Edgar design has a slightly waisted crown and gently sloping brim which add softness to the overall effect

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

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.