Put This On

Harris Tweed Neckties for $30

You won’t get much wear out of them before the weather turns warm, but you’ll be glad to have them come October.  Hats & caps are quite reasonably priced, as well.

(via &)

Q and Answer: The Non-Douchey Hat

Jacob from Seattle writes: I’ve always been a hat wearing type, but only recently have I decided to make an effort to not dress like a 16 year old (up to this point, it’s been pretty much beanies and baseball caps). I work in an office that lets me wear whatever I want, but some upcoming business trips prompted me to buy some more adult clothes. With this, I’d like at least one somewhat classy men’s hat.

I’m looking for something that will look good with a basic slacks/button up/tie. In other words, something nice but not crazy opulent. Is there something you can suggest? 

I see a lot of nice hats being worn by douchebags these days. I would like to wear a spiffy hat, but would hate to be confused with a douchebag. Is is possible for a young-ish man (I’m 27) to wear a fedora without looking like a douchebag?

The answer to your question is that it is certainly possible to wear a nice hat without looking like a douchebag, even if you’re a young man.  A bigger question, though, is whether you are able to, and whether you should.  That’s a bit murkier.

The fedora (and it’s cousins the trilby, homburg, bowler &etc) is second only to the black duster in the heirarchy of Megadork Garments.  Rare is the Dungeons & Dragons game without one player wearing a fedora he thinks makes him look like Indiana Jones.  The sad fact is that these megadorks have tainted the hat for everyone else.  If you want to wear a hat, you have to: A) have a great reason or B) look really awesome.

I figured I’d find some shots of guys looking great in their hats, and so I headed over to the “What Hat Are You Wearing Now?” thread on The Fedora Lounge, the internet’s home for hat enthusiasts.  Frankly, what I found was disheartening.  Some of the hats looked bad in and of themselves, but the bigger problem was the dudes wearing them.  A profusion of bolo ties, acid-washed jeans, fat-guy goatees and other aesthetic nightmares made it hard to see most of the hats as anything other than Superdork Garb. There were even relatively few of what I had assumed I’d see: Costumey Hats, which in my book are one small step above Superdork Hats.

After looking at a few dozen pages of the thread, I gave up, and decided to post the five pictures above, all of which are at least a solid B.

Here are some points to remember when wearing a hat:

• The best way to wear a hat is as functional headgear.  A nice Panama when it’s hot outside, a nice felt hat when it’s cold or rainy.  A hat rarely looks out of place with a suit, tie and topcoat, set against gray skies.  A more casual hat, like the Western hat on the horse guy above, looks great when working outdoors.  Similarly, a modest Panama can look good whenever the sun is shining brightly.
• Wear a good hat.  Unfortunately, even at a specialty hat store, you’ll find relatively few quality hats on the shelves.  Only a few companies still make hats to the standards of the hat you might have bought in JC Penney in the middle of the 20th century.  Many of the ones that did don’t anymore.  Even if you’re at Optimo Hats in Chicago, who make the good stuff, they’ll be prohibitively expensive.  Like cuff links, a hat is something you’ll definitely want to buy vintage.  Get a sense of what shape and color hat looks good on you, and hit ebay.  For a hundred bucks or so, you should be able to buy a great-quality vintage piece - Borsalino is a good place to start, but there are plenty of other choices - Stetson (especially the Royal Stetson line), Dobbs, Locke and so forth.  Poke around on The Fedora Lounge - those guys do know their hats, even if many of them don’t know their, uhm, every other item of clothing.
• Respect hat etiquette.  Don’t wear it indoors unless you’re on your way in or on your way out.
• Most hats will look best with a coat and tie.  That’s just the reality of the situation.  Certainly there are exceptions, but that’s where you’re starting from.
• A stingier brim will make you look douchier, but will also make you look less megadorky.  For a young guy, I think that’s usually a fair trade-off.  If the rest of your style makes clear that you’re not a douche, the hat won’t tip the scales.
• Be awesome in your hat.  If you don’t look great wearing what you’re wearing, you won’t look good in your hat.  You’ll look like a Megadork.  A hat is a sartorial power move, and should only be attempted with confidence and flair.  It also helps if you’re holding a guitar.

A lot of style isn’t about a single item of clothing, it’s about the overall picture.  If someone looks at you and thinks, “that guy’s got his act together,” you can pull off a lot.  Including hats.  If they look at you and think, “this guys a goofus,” you’ll fail.  One item of clothing won’t, generally, be the make-or-break.

I’m a big hat booster - I’ve always loved them, and now that my hair’s starting to thin, they’ve become quite functionally important as well - but they’re a difficult thing to pull off.  They take guts and panache to wear well, and they also require a man who can inspire trust in his audience.  Or just a man who’s super, super handsome.

Q and Answer

Jason writes from frozen Albany to ask:

OK, it is officially really fucking cold. What can the well dressed man put on his head to avoid loosing it to frostbite?

We’re big believers in keeping it simple.  Let’s go with a simple watch cap.

The one above comes from the Billings Army-Navy store, is 100% wool, made to US Navy specs, and costs a grand total of $6.95.  If it is good enough for the deck of a battleship, it’s good enough for your head.  And we like navy blue over black, generally speaking.  The advantage of ordering it from the good people in Billings is that once you’ve got them on the phone, you can ask them to throw in a union suit ($29.95), a brass bugle ($39.95), and a Vintage European Wheelbarrow ($199.95).

Of course, if you’ve got sensitive ears, you could also go with this ladies’ watch cap from Lands’ End, which is 100% cashmere and only $29.63 at the moment.  A little less heavyweight, but a L/XL should fit a pretty sizable man head, and will be nice and soft.  If you’re too embarassed to buy something from the ladies’ section, you can keep your eyes peeled after Christmas as retailers mark down winter accessories pretty dramatically.  My two cashmere watch caps were about $15 each from Banana Republic.

All I Want For Christmas: Jimmy Pardo

In our continuing series All I Want For Christmas, we ask me we like what they’d like to get as a gift.

More than just a comedian, Jimmy Pardo is a gentleman.  No comic has ever staked more of his reputation on the wearing of “a nice pant” and “a hard shoe.”  He spends his days working for The Tonight Show (in a suit, folks) and his nights and weekends as the host of the hilarious podcast Never Not Funny.  In fact, Never Not Funny is hosting a live 9-hour podcast marathon tonight (Friday), starting at 9PM pacific.  They’ll be raising money to repair cleft palates in the third world, so be sure to tune in and donate.  But what does the gentleman’s gentleman want for Christmas?

“Ever since George Michael sang ‘a white cool cat in a trilby hat’ in Wham Rap! (Enjoy What You Do), I’ve wanted one. The only problem? I look horrible in hats. Maybe this one will cure my ills.”

Vintage Trilby, $54 from A&J Esoterica

Trouble in Cooperstown

For many years, I’ve been a customer of The Cooperstown Ballcap Company.  There’s no more quintessential American accessory than the baseball cap, and nobody does it better than these guys.  Their hats are hand-made to your specifications (bill length, crown depth) with almost any logo in the history of organized baseball, not to mention beautiful wool felt and a leather sweatband.  I own four and would be happy to own more - they are a dramatic step up from the New Era stuff at the mall.

But I just got some bad news in my inbox — it appears things are changing in Cooperstown.  They’ll be producing their typical huge variety of custom caps until the end of the year.  Then they’ll be largely shutting down their custom business (making only 20 custom caps a week), and offering only a selection of pre-1960 logos.  They say this is due to a combination of the impending retirement of their head of production and legal issues.

So what can I say?  Make someone’s Christmas dreams come true right now, even if they’re your own.

This is a hat made by fashion types for a mass-market retailer, and it will be purchased by numerous douchebags.  That does not mean it is not lovely.

An aside: this type of short-brimmed, pinch-front hat is called a trilby.

via Selectism