Panama Hat Styles Guide: Fedora, Trilby, Gambler, and More

One Material, Many Shapes

When most people picture a Panama hat, they see a classic cream-coloured fedora with a dark band. But the toquilla straw tradition has given rise to a wide variety of hat shapes — each with its own character, history, and ideal wearer. Understanding the different styles helps you choose a hat that suits not just your taste, but your face shape and lifestyle.

The Classic Fedora

The most iconic Panama hat shape. Characterised by a medium brim (typically 7–9 cm) and a pinched, creased crown. The fedora is endlessly versatile — it transitions naturally from smart casual to formal summer attire. This is the hat that appeared on the heads of Winston Churchill, Humphrey Bogart, and countless Hollywood icons.

Best for: Most face shapes, particularly oval and oblong. Suits both men and women. The go-to choice for everyday elegance.

The Trilby

A slimmer, more fashion-forward variation on the fedora. The trilby has a shorter brim that turns sharply upward at the back and a more steeply angled front. Originally associated with the literary and bohemian world of the late 19th century (it was named after a character in a popular novel), the trilby experienced a modern revival in the 2000s.

Best for: Longer face shapes. Works well in casual and smart-casual contexts. Pairs particularly well with tailored jackets and open-collar shirts.

The Gambler (Boater)

The gambler features a flat crown and a wide, flat brim — the classic “boater” silhouette associated with Edwardian garden parties and Venetian gondoliers. In toquilla straw, the gambler is a statement piece — sun-protective and undeniably eye-catching.

Best for: Round and square face shapes — the angular brim provides flattering contrast. Ideal for beach and garden events, outdoor weddings, and summer festivals.

The Optimo

The Optimo (also known as the “plantation” style) has a distinctive centre crease running front to back along the crown — like a road dividing the hat in two. This shape was popular in the early 20th century American South and has a relaxed, distinguished quality. Many of the finest Montecristi hats are made in the Optimo shape.

Best for: Oval and oblong face shapes. Suits a slightly more formal or vintage-inspired aesthetic.

The Cuenca (Homburg)

Named after the Ecuadorian city of Cuenca, this style has a single central dent in the crown and a rolled-up brim all around. It has a slightly more formal, structured appearance than the fedora.

Best for: Business casual and smart occasions. Suits most face shapes well.

Wide-Brim and Sun Hat Styles

For maximum sun protection, wide-brim toquilla straw hats — with brims of 12 cm or more — are increasingly popular. These have a more relaxed, resort-style character and are especially favoured by women’s fashion. Many feature looser weaves and decorative bands.

Best for: Beach holidays, outdoor events, garden parties. Excellent sun protection (UPF 50+ in tighter weaves).

Choosing Your Style

Our recommendation: start with the shape that appeals to you visually, then consider your face shape and how you plan to wear it. A classic fedora is the safest choice if you want maximum versatility. A gambler or wide brim makes a stronger style statement. A trilby is the most fashion-forward option.

Browse all styles in our Panama hat collection — every hat available in a range of grades to suit every budget.