Cold Weather Essentials: How to Wear Wool Hats

When cold temps strike and you're heading outdoors, let your hoodie off the hook and reach for a stylish wool hat instead. Not only does a wool winter hat keep your head warm, but it's also one of the easiest ways to amp up your wardrobe status.

Whether it's a fedora, newsboy cap, baseball cap, beanie, or top hat, most wool hats are versatile enough for both men and women, so you'll never run out of options. But with so many choices, it can get a little overwhelming.

To save you time sifting through all the different styles of wool hats, take a look at our curated list of the coolest styles along with a few styling tips on how to wear them.

But first, make sure you've got your head on straight by consulting our guide on how to determine your hat size.

Wool Fedora

There's something so timeless and alluring about a fedora. It's a classic style that has been captivating the public ever since 1889 when famed French actress Sarah Bernhardt appeared onstage wearing a soft-brimmed hat with a center crease.

Fast forward to today and it's the ultimate accessory for your winter wardrobe that can be dressed up or dressed down for any occasion. Simply put one on and, much like Bernhardt, you're sure to get noticed.

We recommend a fedora with a medium or wide brim, but if you're considering a short-brimmed version, learn the difference between a fedora and trilby so you avoid any fashion faux pas. Find more options in our list of the best fedora hats for her and the most stylish wide-brim fedoras for him.

How to Wear It: Put the finishing touch on a faux fur coat or blazer and button-down with a wide-brim fedora for a can't-miss contemporary look.

Wool Newsboy Cap

Cold Weather Essentials: How to Wear Wool Hats - Newsboy

Extra, extra! When you want a stylish add-on that's not as formal as a fedora but dressier than a baseball cap, it's time to pick up a newsboy cap. Although named after the newsboys who wore this rounded, button-top hat style back in the early 20th century, newsboy caps aren't just for guys anymore — they're just as fashionable for ladies.

Try one in plaid wool or antique leather to add instant sophistication to any outfit. Newsboy caps often get confused with flat caps, which are another great wool hat option. But they're not the same. Read our primer on the newsboy cap vs. flat cap and you'll soon know how to easily spot the difference.

How to Wear It: Layer your newsboy cap with a long-sleeve shirt, cashmere sweater, navy-colored pea jacket, or camel coat for a classic touch.

Wool Beanie

Cold Weather Essentials: How to Wear Wool Hats - Beanie

It might be simple, but it's far from basic. A beanie is one of the most universally flattering and appealing hat styles for men and women any time of year. But a warm wool beanie is a winter-weather essential when you're hitting the mountain slopes or strolling the city streets. Whether you opt for a close-fitting version or a looser style, beanies look good with long hair, short hair, straight hair, curly hair, or no hair!

Because these "sock caps" have such a straightforward silhouette, feel free to get creative with different colors as well as beanie styles — slouchy, cuffed, or pom-poms, perhaps?

How to Wear It: Pair a simple beanie with a brightly patterned scarf and sleek leather jacket for an effortlessly cool look. For more beanie looks, don't miss our guide on picking the best beanies for any season.

Wool Baseball Cap

Chances are you already have at least one baseball cap in heavy rotation, but a baseball cap made from wool should be part of your winter gear. Granted, it might not keep your head as warm as a fur hat or wool beanie, but any head covering is better than none.

Plus, the benefit of a baseball cap — whether it's a snapback, strapback, or fitted — is that it's one of those hat styles that anyone can pull off without trying too hard. Just remember that laidback does not mean messy. Keep your hat clean with these three simple methods.

How to Wear It: Keep it casual with a heavy parka or other winter jacket — just don't wear it backwards or (gasp) sideways. You're a grown-up after all.

Wool Top Hat

No longer for the horse-and-carriage set, the top hat is making a major comeback in mens fashion. With its distinctive tall crown and slightly curved brim, this dramatic headgear has certainly evolved from the Abraham Lincoln toppers of yesteryear.

Whether it's a street-art style splashed with paint to slightly shorter versions in different colors, these modern designs offer daring new twists on an old favorite. By the way, if you don't speak hat, you can brush up on your hat vocabulary with our guide to the anatomy of a hat.

How to Wear It: Forget the tux. You don't need a special occasion to wear a top hat because wearing a top hat is the special occasion. Combine it with an all-black ensemble — blazer, T-shirt, jeans — and a white pair of sneaks for a downtown look that defies tradition.

Woolly Wonderland

When the cold weather hits, there's no better way to keep your head warm and your style cool than a wool hat. From casual baseball caps and beanies to swanky fedoras and top hats, there are plenty of options to suit your personality and lifestyle.

Check out our latest selection of mens wool hats and womens wool hats, plus easy-to-follow tips on how to clean a wool hat so you can enjoy your own season after season.

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