1950s Men’s Straw Trilby by Churchill | Cool Summer Style
$55.00
Shop this 1950s Churchill straw trilby hat.
This 1950s men’s straw trilby is for a smaller head; please check your hat size.
✅ Approx. Hat Size (cm): 7 (20″) Outside Diameter: 11″ (48); Height of Crown: 4.5″ (6); Brim Width: 1.75″ (15).
✅ Condition: Very good.
✅ Era: 1950s.
✅ Mark/Label: Churchill
✅ Only One! Domestic Flat Rate Shipping – Hats: $10.00
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.
VINTAGE CONDITION
SHOP MORE VINTAGE HATS
HOW TO MEASURE YOUR HAT SIZE
HOW TO FIND YOUR HAT SIZE
- Pull a fabric tape measure or length of string around your head just slightly above the ear, across the mid-forehead, completely circling your head.
- Hold the tape firmly, but not too tightly. You are measuring your head exactly where the hat will sit in either inches or centimeters.
- If your measurement falls between sizes, choose the next largest size.
- Then buy a fabulous vintage hat from Madge
SEE OUR HAT SIZING CHART
WHAT IS A TRILBY
What is a Trilby
Most people have heard the term fedora as a style of hat but fewer know its sibling, the Trilby. Very similar to a fedora in shape, the Trilby has a narrower brim in the front with an upturned brim in the back. Trilbies are also sportier, made in a variety of patterned wool felt, including plaid, checks, and tweeds. Fedoras have a wider brim all around the crown with no upturn. Fedoras are also usually plain wool, beaver, or fabric.
ABOUT CHURCHILL HATS
Churchill Ltd. was a maker of men’s hats known for producing refined mid-century styles with quality materials and traditional craftsmanship. During the 1940s and 1950s, Churchill created classic felt and straw hats that reflected the streamlined tailoring and sophisticated casualwear popular in postwar menswear.
HOW TO CARE FOR YOUR VINTAGE HAT
Vintage Hat Care
Always handle vintage hats by the brim, not the crown. Store them in a cool, dry place away from direct sunlight. Keep them in a hatbox or covered with acid-free tissue to prevent dust. Avoid using modern sprays or steam, as these can damage delicate materials and trims. For reshaping or cleaning, it’s best to consult a professional milliner experienced in vintage restoration.
SHIPPING & RETURNS
We ship items within five business days. Occasionally, there might be shipping delays. If this occurs, we will promptly notify you.
Clothing and accessories ship via USPS Priority Mail, UPS, or FedEx, selecting the best option based on price and insurance. Jewelry ships either First Class or Priority. For overseas orders, we use International First Class. Please refer to our Shipping Information for detailed rates.
International buyers are responsible for all customs duties. PLEASE NOTE: Starting July 1, 2021, EU members will incur VAT taxes based on the specific country’s tax rates during importation.
We know you may be wary about buying vintage items. If so, we do offer returns. If you receive vintage pieces and are dissatisfied or if the item doesn’t fit, please inform Madge of your return request within 10 days of receiving the merchandise. You must return the items within 30 days after notifying us.
You can find our complete Return Policy here. If you have further questions after reading, please call or text (404) 850-1757.
SIGN UP FOR SPECIALS & DISCOUNTS
Photos copyright © 2026 Madge’s Hatbox Vintage. Join our Facebook group, Mad About Vintage, for weekly specials.
