The original Baseball Cap was made famous by the Brooklyn Excelsiors who first wore a version of the six panel cap in 1860. Before it was known as the “Baseball cap” it was called the Brooklyn cap. The classic six panel cap is the most famous form of headwear today and the choices are limitless.
Start with the setting and finish you want. Choose the Kentucky Waterproof Oiled Cotton Cap for wet-weather use; choose the Henry Long-Bill Organic Cotton Newsboy Cap for a casual everyday option. Newsboy designs including the Merrik, Brent, and Sinclair offer different fabric-led looks, while the Alfred Herringbone Drivers Cap and French Beret create a more tailored silhouette. Genuine leather brings a distinctive finish in the Amalfi Cap Check each product listing for its available size, since the collection includes Small through XX-Large as well as One Size and adjustable fits. For care, follow the instructions listed for the specific material and product.
Conner's newsboy cap collection combines vintage British heritage with sustainable, handmade craftsmanship. Each cap features the classic 8-panel construction with a rounded, full crown and signature top button—the hallmarks of an authentic newsboy (also called Gatsby, paperboy, or baker boy caps).
Unlike flat caps (which have a sleeker, low-profile design), newsboy caps offer a fuller, more expressive silhouette with visible paneling that creates texture and dimension.
A newsboy cap (also called a Gatsby cap, paperboy cap, or baker boy hat) is a rounded cap with 8 triangular fabric panels sewn together from a center button, creating a full, puffy crown. It features a small, stiff brim and sits higher on the head than a flat cap. Newsboy caps originated in the late 1800s and were popularized by newspaper delivery boys in Britain and the United States.
Newsboy caps have a rounder, fuller crown created by 8 panels meeting at a top button, giving them a baggy, vintage look. Flat caps (also called ivy caps or driving caps) have a sleeker, low-profile design with fewer panels and no top button. Newsboy caps sit higher and looser on the head, while flat caps hug the head closely for a minimalist silhouette.
Conner newsboy caps include styles made from organic cotton and weathered cotton. Organic cotton is grown without synthetic pesticides, while weathered cotton offers a vintage look and durability. Check each product page for the materials used in a specific style.
A newsboy cap should sit comfortably around your head without being too tight or loose. Measure your head circumference just above your eyebrows and ears using a flexible tape measure. Match your measurement to these Conner size ranges: Small (21 1/4-21 5/8 inches), Medium (22-22 3/8 inches), Large (22 3/4-23 1/4 inches), and X-Large (23 1/2-24 inches). The cap's fuller crown allows for a more forgiving fit than flat caps. Two free size inserts ship with every order.
Yes. Newsboy caps can be a stylish choice in 2025. Their vintage-inspired look works for men and women, pairing with everything from casual jeans to tailored coats.
Newsboy caps pair well with smart-casual and vintage-inspired outfits. For men: wear with sport coats, knitwear, denim jeans, and boots for a heritage look. For women: style with tweed jackets, scarves, leather gloves, and autumn layers for a retro-chic vibe. The cap's rounded silhouette complements oval and long face shapes particularly well, while the vintage aesthetic suits both casual strolls and elevated weekend wear.
Yes, if you choose a breathable material. Conner's organic cotton and weathered cotton newsboy caps are lightweight and allow airflow, making them suitable for spring and summer wear. Avoid heavy wool styles in hot weather, as those are better for fall and winter. The cap's brim can provide shade for your eyes and face during outdoor activities.
Care depends on the material. Cotton caps: spot clean with a damp cloth and mild detergent; avoid machine washing as it can deform the cap's shape. Wool caps: brush gently to remove dirt; use a steamer to reshape if needed. Genuine leather caps: wipe with a slightly damp cloth; condition periodically with leather conditioner. Store your cap on a flat surface or hang it to maintain its shape. Never put newsboy caps in the dryer.
Conner's Limited Lifetime Guarantee applies to purchases made at connerhats.com. For a workmanship failure within the first 12 months, Conner provides a free replacement of the same style, size, and color, with shipping paid. After 12 months, a replacement is 40% off, with shipping not included. Material degradation from use qualifies for a 30% off code. If your hat is lost or stolen, you can get 50% off the same hat, with shipping not included.
Yes. The hats in this collection use organic cotton, weathered cotton, water-resistant cotton blends, oiled cotton, Australian wool, wool blends, and genuine leather. The brand runs its original St. Augustine warehouse on 100% solar power (orders now ship from American Fork, Utah), requires its suppliers to pay fair wages, and has worked with trusted factories since 1999. We still maintain our company food forest at the site and have created a hub there for other small businesses to use the location. Conner's commitment to sustainability extends across materials, production, and long-term partnerships.
The Kentucky Waterproof Oiled Cotton Cap is the clearest choice when waterproof construction is your priority. Other caps in the collection use materials such as cotton, wool blends, or genuine leather, so check the individual product description rather than assuming every style has the same weather protection.
Yes. A Hat and Cap Clip for the Wind is included in this collection as a separate accessory. It is useful when you want added security in breezy conditions. Check the accessory listing for its product details and suitability with the cap you plan to wear.
