The Business of Wearing Hats

There is an excellent guide to buying and wearing hats in the new issue of GQ. Interesting to see that Manhattan’s JJ Hat Center was featured prominently. You may remember back in June when CBS Sunday Morning did a segment on hats and featured the same store and incidentally, the exact same salesman. The handy guide from GQ basically breaks down everything you need to know to wear a hat without looking like you just got off a flight from LAX. Much respect to GQ for making the guide without including pictures of Justin Timberlake or Brad Pitt.

My good friend Mark wears a hat frequently with a suit and ends up looking very smart. When well done, there is no better accessory. Take a look at Don Draper if you don’t believe me.

Comments on “The Business of Wearing Hats

    mho119 on September 16, 2008 12:55 PM:

    I’m all for hats but don’t really like this article. My father always used to wear a hat to his office but I have to say that they work so much better when dressed down.
    As great as Don Draper is- and I think he is unparalleled- you’re probably never going to look like he does. That goes especially if you’re reading blogs about hats, because lets face it, the last thing Don Draper would ever do would be to research how to make a hat look good on himself. He really wouldn’t care, and that’s half the reason he is the man.
    When it comes down to it, the guys in the suits and hats in the GQ article just come off looking like they’re trying too hard while Andre Benjamin and the guys dressed down come off looking much better.

    Ryan on September 16, 2008 1:06 PM:

    I agree abit with that ^

    I think Andre and Mr. Depp are a some of the best hat wearing men out there. I prefer the dressed down look myself as well, unfortunately none of those hats look very good on me. I have to resort to speech to make a statement…

    Michael Williams on September 16, 2008 1:57 PM:


    I appreciate the comments and your thoughts, but I have to respectfully disagree. I think Don Draper can pull off a hat because he has confidence in his look. Same goes for my friend Mark who routinely wears a hat with a suit. He has confidence in his own style, so wearing a hat doesn’t look out of place or like he is “trying too hard.” Getting back to Draper, no he wouldn’t do research on a “blog,” his father would have taught him how to dress or he is just conforming to social norms (as most professional men in the early sixties wore hats with suits). To me, wearing a hat is more about chutzpah than your personal style, dressed up or down.


    Charles Bixx on September 16, 2008 3:05 PM:

    I think men have forgotten how good we can look in hats. Once we remember how masculine a hat can look, perhaps we’ll wear them without outside prompting.

    Charles Bixx

    Edward on September 16, 2008 5:22 PM:

    No love for noted hat aficionado Mos Def?

    angelo on September 16, 2008 7:23 PM:

    Although I’ve no qualm with this, I’m waiting for the menswear fervor surrounding Mad Men to quell. Let’s look to the young, not the old.

    chris on September 16, 2008 8:28 PM:


    I think the point you were making is that anyone who has enough confidence (or chutzpah?) to successfully pull off wearing a hat either dressed up or down would not be researching the ‘right’ way to wear said hat. The hot, confident guy would just wear the hat- and not because a fashionisto instructed him on the fierce way to do so. Bottom line- if you are googling ‘how to look cool in hat’, chances are you will not. Agree with that point. However- have to say that I personally prefer hats dressed up.

    Michael Daddino on September 16, 2008 9:50 PM:

    Much as I love them, I am a little perturbed by the recent hotness of hats: their deployment seems to be too narrow. Perhaps out of natural perversity, I’ve been gravitating towards as-yet uncool choices: cowboy hats, for one. And I definitely want to get a bowler.

    Michael Williams on September 16, 2008 10:21 PM:

    Chris — did you just say “fierce”? Seriously? That is uncalled for.


    Cator Sparks on September 16, 2008 11:52 PM:

    ACL- This first post I think I will ever disagree with!
    Mostly because of JJ Hats. I am all about classic, traditional and Americana but I see men wearing such hats on the street and it just looks like a costume from a gangster movie. I’ve always thought Jared Paul Stern looked so silly sporting a wide brimmed drab hat around town.
    I also have to admit that you mentioned the two men who have made the hat industry popular today- Justin and Brad, who are also clients of my house mate Rod Keenan.
    Andre Benjamin is also a client.
    Rod is the only man in America making custom made, hand sewn hats, an amazing craft in itself. Not sure the designers at JJ touch every hat that comes out of their shop, not to say I am not find of some of their styles.

    I have been wearing hats for 10 years now, almost on a daily basis and if you know your personal style you dont think twice about sporting one with jeans, a suit or off to the beach.

    And for Chris- yes he makes bowlers and cowboy hats!

    Michael Williams on September 17, 2008 12:02 AM:

    I’m not saying that you can’t wear a hat and be dressed casually. I am merely making the point that I prefer a hat with a suit. And Cator, we are indeed in disagreement. I’m not a fan of the Pitt / Timberlake style or lack there of.

    This just illustrates my point:

    That is not cool.

    retep tterrab on September 17, 2008 1:47 AM:

    Wow, wow, thank you, well played; and how ever you want to say it: Hats are a grand endeavor to any man’s wardrobe. And any advice to wear then properly is an admirable public service.

    I’ve been told that I have a head for hats (and a face for masks) and much appreciate any guidance – to men at large – in these matters.

    My current favorite is a bright red cycling cap made from felted cashmere. It is a product of the Vanilla workshop in Portland, OR. and at 70 dollars is an absolute bargain for its quality and construction.

    Peter Barrett

    Cator Sparks on September 17, 2008 10:38 AM:

    Friendly fire as they call it! I see your point, but a Rod hat will always be my pick over JJ.

    Chris on September 17, 2008 10:55 AM:

    Yes, yes I did. Just trying to drive home fashionisto point. Won’t happen again.

    lefty on September 18, 2008 9:35 AM:

    Check out for plenty of hat info.

    Greg in Tennessee on September 18, 2008 10:46 AM:

    If Mr. Otsuka has a “round compact face” I am a monkeys’ uncle… makes the rest of the article somewhat suspect, IMO.
    In some parts of the world (notably vast swaths between NYC & LA) hats never went away. Looks as though the poser brigade has latched on to them for their flavor of the month, swell.

    Steven on September 18, 2008 7:14 PM:

    Any article that encourages men to wear hats is great. We have been in business for 60 years in Brooklyn and are seeing a major revival in hat wearing among young men today.

    PAN on September 23, 2008 5:41 AM:

    Surprised Still Life NYC in Manhattan’s lower east side didn’t get a nod…sick collection of custom, hand-crafted crowns (soon to be opening its own millinery factory in Red Hook, Brooklyn).

    Still Life’s owner, Frenel Morris was featured in one of this month’s GQ Rules segments as well…

    abh1wordpress on December 6, 2008 1:25 PM:

    It’s great that the hat has come back.

    A hat makes a man look taller. It hides thinning hair. It imparts gravitas and authority to its wearer.

    It protects your face from the sun. It may make one look older, but it keeps one from getting older quicker (wrinkles).

    Rob J on May 10, 2009 1:14 PM:

    A very good article. I have been wearing hats for many years, and recently found a mint condition homburg in a second hand shop. I haven’t seen anybody wearing one for many years, but I cannot wait to see the reaction of my friends when I do.
    One thing your article did not point out, the fairer
    sex always compliment a man in a nice hat. Take it from me, it’s true.
    And now that the superb “Mad Men” series has just evoked that style of bespoke suits plus a decent hat, just watch the fashion industry start to prick up their ears for future tips…..
    As FS may have said once said “It’s a gas !”
    By the way, much has been said about Sinatra, the women, fights, the Mob etc, but little is ever mentioned about his epic battles against racism, at a time when it was very dangerous. Check out the YouTube footage of FS with Satchmo from 1957, and Ella from the same year. Nobody had the guts to perform with African American entertainers with such ease. Civil Rights came to FS, and not the other way around.

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