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Style Guide: Winter Hats For Men

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Style Guide: Winter Hats For Men

You promised yourself that you would start wearing a winter hat to avoid the overwhelming discomfort of going without when in the frosty winter cold. However, upon mentioning to the store's sales associate that you want a "winter hat," you weren't exactly prepared for the onslaught of related questions: "What type of fabric?" "What style?" "For work or play?"

While many winter hats are one-size-fits-all, this is most certainly not a one-hat-works-for-every-man scenario. Rest assured, however, your ideal winter hat awaits:

Are You Looking For A Winter Dress Hat?

Walking into the office with the hot orange beanie you picked up from the convenience store in a desperate attempt to warm up last Saturday – it’s going to garner some uncomfortable stares. Whether you’re on your way to work or a special dinner date, a winter dress hat is in order.

  • Fedora: The classic hat you’d expect to see in a Humphrey Bogart film.
  • Stingy Brim Fedora: Just like your classic fedora, but 1.5 inches or less of a brim that rolls up and often snaps in place.
  • Wool Porkpie: Prepsters, hipsters, artists and jazz club enthusiast types will love the cool wool version of this round classic.
  • Flat Cap: Made in corduroy, leather or wool, seek out this cap with a built-in underbrim.

Do You Need Protection From Daily Chilly Weather?

When you’re running errands or taking part in other general daily experiences that do not require any particular snazzy attention to your look, opt for a more casual approach to keeping your cranium nice and cozy. No matter your personal style, the classic winter solution (which works whether your style leans toward a classic, prepster vibe, laid-back California wear, urban street style or anything in between) is the beanie.

Granted, you may call it a toboggan or some other name, but whatever title you assign to it, this hat is a knit cap that is meant to fit tightly near its brimless hem. You may have a particular image in mind; likely a hat composed of wool with a bottom that folds up once or twice. However, when choosing a beanie to fit your aesthetic, you will find a surprisingly diverse selection to fit your specific wants.

Fabric Options:

Appearance Options:

Do You Need Heavy-Duty Warmth?

  • Working Outside All Day? If you’re working outside all day or enjoying time spent outdoors in cold weather, you’re most concerned about your comfort and literally protecting yourself from issues like hypothermia and frostbite. You’re in need of a hat constructed specifically for low temps.
  • Protect Your Ears: And about those ears – if they tend to get extra chilly, start with a trapper hat for easy-to-wear flaps that cover your ears when you need them and tie up when you don’t. Beanies made with twice (or more) the material or Sherpa lining offer a great deal more warmth than their lighter weight forms.
  • For Severe Winter Weather: If you’re really in need of serious protection from winter weather, there’s always the balaclava (also known as a ski mask), which essentially covers everything but your eyes – sort of like a hat and scarf all in one piece.

Do You Usually Wear Hats For Extra Sun Protection?

When it becomes clear you can no longer wear your favorite baseball cap because it’s doing nothing to keep you cozy, go for a winter beanie with a visor. You’ll still have a similar look (and the extra eye protection from the sun that you’re accustomed to), without having to shiver in the name of your personal style.

Do You Want To Avoid Helmet Hair?

Maybe you’ve got a pretty fantastic head of hair and the idea of smashing your stylish coif with a hat is extremely frustrating. Or, perhaps you’ve got the winter dress hat all sorted out, but your ears are still subjected to the winter chill. This is when ear covers come in handy. You have a few different options depending on your needs:

  • Earbags: These babies are not connected. You simply slip one over each ear to keep them nice and warm.
  • Ear Warmers: Much like the classic earmuffs, which are two warmers connected with a headband, the modern versions are more utilitarian and made to be worn behind the head rather than over it. Your ‘do will remain intact, and you can typically wear these beneath a hat.
  • Headbands: A single band of material, these will potentially mess up your hairstyle but are easily worn beneath a hat for extra ear coverage.

When that blustery breeze kicks up and you make it through surprisingly warm and unscathed, smile and find yourself feeling just a little bit sorrier for that guy in the baseball cap, holding his gloved hands up over his bright red ears.

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