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?

Most sales discount 20 or 25% off.  Sometimes free shipping is dangled out there.  But it’s rare when a 30% off sale hits all three GAP Inc. family brands at once, and they throw free shipping on top if you spend more than $100.

If you’ve been sitting on your hands waiting to upgrade your fall wardrobe, now’s not a bad time to take advantage.  The sale only lasts through Tuesday.  Merch that’s already on sale seems to also be included.  Here’s some decently smart picks to help you take the greatest advantage of this offer:
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B.R:  Merino V-Neck – $41.65 (reg. $59.50) | Wool Stripe Scarf – $41.65 (reg. $59.50)

Usually $126 for the two plus shipping. Now $83.30

First the bad news.  It looks like Banana Republic is phasing out the cotton/silk/cashmere blend v-necks.  Instead they’re bringing in a more expensive cashmere/silk only blend.  And those will cost about $15 more, running $74.50 retail.  No thank you.  Too bad, because that cotton/silk/cashmere blend was one of if not the best v-neck on the market.  A close second is their Merino Wool v-neck.  Slim, warm, and not scratchy, at 30% off one of those will come in just over $40.  Scarf weather is well on its way.  $60 is too much for this navy and orange scarf even though the stripes are dead on.  Knock 30% off, lump it in with the sweater to get free shipping, and all of a sudden those two wool pieces cost you a grand total of $83.30.
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At GAP:  Wool Herringbone Blazer – $68.60 (reg.$98) | Rugby Stripe Socks – $4.19 (reg. $6)

Could look great together. Especially at this price.

Of course that blazer is two bucks under the threshold for free shipping.  It’s like they’ve got an algorithm for this kind of thing.  So to beat the system, drop six bucks more on some on-sale bold rugby socks, and know that since shipping is $7.00… you’re getting a free pair of socks (plus a buck back) even before the 30% discount is applied.  Which by the way, once that discount is applied, total cost shipped is $72.79.  Only drawback is that some sizes on the blazer are on back order.  It’s worth the wait.
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At Old Navy:  Lots… $101 before discount & shipping, $70.70 after with free shipping.

Not bad for $71

Brown Stripe Blazer – $34.65 (reg. $49.50)
Solid V-Neck - $9.80 (reg. sale $14.00)
Rugby Stripe V-Neck - $14.00 (reg. sale $20.00)
Marled Sock - $3.50 (reg. $5.00)
Cable Knit Hat – $8.75 (reg. $12.50)
This took a little prep work so assuming that the sale prices on the sweaters hold, you’re looking at just over $100 total, so free shipping, then the 30% discount with the code drops it to $70.70.  The blazer will need tailoring, but once that’s done it should fit great.  I’ve got two Old Navy blazers in my own closet and they’re my go to for every day at the casual workplace, or headed to the bar for happy hour.  The rugby stripe sweater has already been tried on and reviewed, and hopefully the solid is of the same cut.  You can never have enough socks, and a backup cable knit hat ain’t a bad idea either.

The sale lasts through Tuesday.  Online only.  Must use code: SAVEBIG at checkout.  Free shipping only kicks in after you’ve spent $100 or more.

Dear Bill:

It’s over.  Your stranglehold on the AFC and the NFL is done.  Sure it’s been fading for a good while, but the mud-hole that the Raven’s stomped in your behind on Sunday only secured your fate.  And I’m sorry to say, your hat was not just a sign of your impending demise, but a partial cause.

Only a grown man who has such an overblown ego that he thinks he sh*ts ice cream would wear a hat like that.  And what makes it even worse?  It wasn’t even that cold outside.  Twenty Degrees?  Twenty Degrees and you feel it necessary to wear a hat that only Ralphie’s little brother from A Christmas Story  would wear?  Football is a violent contact sport.  How are the athletes whom you coach supposed to follow your leadership when you look like you aren’t fit to sit at the front of the toboggan?

You suck.  Your opinion of yourself is out of control.  You deserve all the failure that’s coming your way until you get your act together.  You could have worn this hat, or this one… or hell, one of those tall numbers that the Grenadier Guards in England wear.  At least that would have been funny.

The Pom Pom makes you look like a pathetic 1st grader who couldn’t wait to get the game over with so he could run inside and have his Swiss Miss.  We haven’t seen such inappropriate attire for the situation since Matt Lauer turned Afghanistan into a Burberry runway.

Your Quarterback can sometimes dress a little too snooty.  Yet you dress like a homeless man with mental issues.  We’d tell you it’d be best to find a middle ground, but… that would mean we’d like to see you win.  And we don’t.

Have a nice off season!

Signed,

Dappered

P.S. Winter hats with Pom Poms aren’t the only clothes women hate.
Here’s our list of the other things you might be wearing that are killing your chances with members of the fairer sex.

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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