From the Mailbag:

Hey Joe,

Winter is doing its thing where I live, and the temperature is rather chilly to say the least (the high last Wednesday was 4 degrees).  I’m all set, with my heavy pea coat, gloves, scarves, etc.  However, my head remains, in a word, freezing.  Do you have any ideas for headgear other than a standard beanie?  Something that combines fashion and function, or should I just wear my beanie with pride?

- Aaron

Thanks to Aaron for writing in, and I wish I had a better answer.  You gotta wear your winter hat with pride.  Yes they mess up your hair and yes they make you look, from the neck up, um… phallic.  But the alternatives just aren’t acceptable.

The first problem with other options like driving caps or fedoras is that on most (but not all) men, they look forced.  The second problem is that they all leave your ears unprotected.  And if your ears are stinging because it’s that bitter cold out?  Your hat ain’t doing its job.  It’s got to keep you warm, and that’s why you also need to go with wool and not cotton.

Unlike cotton, wool will still keep you warm even if it gets wet.  And wet things seem to fall from the sky this time of year.  Here’s three basic styles to consider:

Ribbed Watch from Woolrich. Italian cashmere blend. Under $40.

#1. The Watch Cap:  Ralph Lauren Merino Wool – $35.00

Knit with a flip up bottom, watch caps were designed to keep the heads of soldiers or sailors warm when they’re on watch.  Usually they’re dark and match the wearer’s coat (most often a peacoat).  But since Camel is huge this year, flip the script on buying a new camel coat and get a camel/light brown hat instead.  Like this one.  100% merino wool.  Wear it with your black peacoat and it’ll stand out in a good way.  There’s also your local Army/Navy Surplus.

#2. The Cable Cap: J. Crew Wool Mix – $48.00

Cable knits are just more expensive.  But they do offer a little more bulk, warmth, and if you keep it dark, subtle texture.  Women look best in cable knit.  Especially sweaters.  Guys can still pull off a cable knit cap.

#3. The Fair Isle Cap:  Banana Republic Fair Isle Wool Mix Beanie – $29.50

Throwin’ a bone to the Fair Isle fans here.  I’m not a fan of the Fair Isle pattern when it thunders over a sweater like an invading horde.  But if it’s done lightly, in a similar shade, and it’s on something you take off when you come inside like a hat… well then have at it.  Oh, and I’m gonna guess that the hat you see above isn’t made in Scotland.  (Thanks to our pals at TheNextBarStool for the link)

Too boring or minimalist?  Would you wear something like this?  Or this?  What’s your go-to hat?

Face it guys, women wear red better.

(see example above, and below…  Blake Lively at the 2009 Emmy Awards)

Bright Red always looks a little too Christmasy on guys.  Women wear it and they’re stunning.  Guys wear it and they look like they’re gearing up for another bad sweater party.

That’s why a bright red winter hat actually works.  You’ll only be wearing it a few times every year, and it’ll be during the holidays.  Keep it solid (no white snowflakes) and you’ll look, well… festive… but not so festive that you might be ready to launch into Good King Wenceslaus.

That, and the black winter hat and black overcoat combo makes you look like you’re about to rob a bank.

T-shirts and other under layers can look great in dark red.  One of my favorite t-shirts is a solid dark red.  It’s often under other shirts or worn on the weekends around the house.

Use red sparingly, and encourage women to use it often.

(More pics of Blake in her Red Dress can be found here.)

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