Men’s Straw Trilby by Churchill | Cool Summer Style (Copy)

Classic mid-century summer style with just the right amount of swagger.

Vintage Trilby Details

This 1950s Churchill straw trilby features a warm honey-toned woven straw body with a sharply pinched crown and a narrow brim that curves slightly downward in front. A layered brown striped grosgrain ribbon hatband adds rich contrast and gives the hat that unmistakable vintage lounge-era feel.

The interior retains its original leather sweatband and Churchill label, marked size 7. Lightweight yet structured, this is the kind of hat that looks equally good with linen tailoring, a camp shirt, or worn casually with rolled sleeves and sunglasses on a hot summer afternoon.

Churchill hats were known for quality craftsmanship and refined styling, and this example captures the sleek, easy sophistication that defined men’s fashion in the 1950s.

• 1950s vintage men’s trilby hat.
• Churchill label.
• Honey tan woven straw.
• Brown striped grosgrain ribbon hatband.
• Leather sweatband.
• Size 7.
• Narrow brim upturned in the back.
• Pinched crown.

Why We Love It:
It has that effortless Sinatra-on-vacation energy that never really goes out of style.