How to Wear an Ivy Cap, Plus the Best Picks for Your Style

They’ve been around for centuries, but if you ask the average person what an ivy cap is, they might respond with a perplexed look. That's because unlike baseball hats, an iconic American wardrobe essential, ivy caps have remained a bit under the radar…at least in the States.

Also referred to as a flat cap, crook cap, or driving cap, an ivy cap is a classic style that dates back to 14th century England with similar subsequent versions found throughout Scotland and Ireland. In the late 19th century and throughout the 20th century, the flat cap became a more common sight in America, but it never took off like it did in the U.K.

So what exactly is an ivy cap? It's a rounded cap with a low profile and a small, stiff brim. Another common name used for ivy caps is newsboy cap, but that's a mistake. The most noticeable distinction between the two styles is that newsboy caps are rounder and puffier. Most often constructed from tweed or cotton, ivy caps are ideal for cold weather (London fog, anyone?) and have long been a staple of winter wardrobes across the pond.

However, in more recent years, this flat hat has been making fashion waves right here in the USA from NYC to Hollywood. Thanks to celebrities such as British import David Beckham, LL Cool J who has been rocking Kangol caps for decades, and Pharrell who always keeps things fresh, the ivy cap is experiencing a fashion renaissance.

Originally a mens hat, today's ivy caps are worn by men and women alike. The flat cap style is proving popular as a sporty yet stylish alternative to other styles — it's a less formal hat than a fedora, but not as casual as a baseball hat. Before you head out to your local hatshop or go shopping online, let our guide help you find the ivy cap that's right for you.

(Psst. if any of these hat terms are new to you, check out our post: "the anatomy of a hat.")

Flat Cap Checklist

Great Ivy Caps You'll Love

How to Wear an Ivy Cap, Plus the Best Picks for Your Style - Leather cap

Traditionally made of tweed, modern ivy caps come in a variety of colors, patterns, and fabrics that include cotton, wool, cashmere, silk, leather, linen, and synthetic materials such as polyester and acrylic. For the full spectrum of ivy caps, be sure to check out our selection of the best ivy caps. Here are some of our favorites we think you'll love.

A True Classic

Leather done right turns an outfit into a statement. Make your statement this winter with the Sabre leather ivy cap by Stetson. Made of weathered leather, the Sabre ivy cap by Stetson features full lining to keep you comfortable, especially during those chilly fall and winter months.

Low-Key Luxury

Fall golf days are perfect for wool flat caps. The Radcliffe ivy cap by Stetson is made with a wool blend, complete with a plaid print, and will make you feel like the links are never too far away. This cap is a fantastically fashionable cool-weather option. Understated, lightweight, and supremely versatile, you can dress it down with a T-shirt and shorts or step it up with a button-down and khaki pants.

It's In The Details


Sometimes your wardrobe needs a little something unexpected. That's why the Onassis leather ivy cap by Stetson, an all-weather lamb leather ivy cap with plaid lining, should be your next purchase. It's a classic style with a modern feel, and it suits your getup no matter the occasion.

Cool and Casual

How to Wear an Ivy Cap, Plus the Best Picks for Your Style - Cambridge

The Cambridge ivy hat by Stetson is the perfect pick when you want the comfort and feel of a baseball cap with a more refined sense of style. Made with a water-repellent cotton blend, the Cambridge is simple, durable, and great for splashing around in the California sun as well as protecting your head on those grey rainy days.

Understated Elegance

You don't need to be in the English countryside to look like a dapper gentleman (or gentlewoman). The Greystone ivy cap by Stetson is all about quality and comfort — you'll love the Flat caps turn any spring weekend event into a wedding-like affair. This polyester ivy hat is just another reminder that the right piece can take your day from here … to here.

A New Essential

Whether you're a newbie to the flat hat craze or a longtime fan, the bottom line is that wearing an ivy cap is a fun and fashion-forward way to expand your wardrobe and mix things up. Now that you know more about what an ivy cap is, where they came from, and how to best wear one, it's time to get in on the action. No matter the time of year or your personal taste, you can be sure that there is an ivy cap to suit your own style.


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