Easy and Elegant Life

The Search for Everyday Elegance and the Art of Living Well.

The Way You Wear Your Hat

(Image by Bettman/Corbis and used without permission. Let me know if it has to come down, please.)
Image by Bettman/Corbis and used without permission. Let me know if it has to come down, please.)

Can a man pull off wearing a hat forty-eight years after President Kennedy killed the practice? Do you think we’ll see President Obama taking the victory lap in his topper after taking the oath of office? I doubt he’ll wear the Sox cap with his topcoat, no matter the weather.

Which brings up a point, by hats I mean hats. Not caps, be they baseball or flat. I mean fedoras, trilbys, skimmers, cokes (bowlers), Lord’s, porkpies and Homburgs. After all, you can’t wear a cap with a trenchcoat or a raincoat. It just doesn’t look right.

But hats can be difficult to pull off. Mr. Grant does nothing to detract from his famous mug. He carries his in several scenes from “Indiscreet.”

Yes, hats can be tough. Especially if you, like I, wear glasses. A hat ages me quickly.

But today it was raining. And my dog’s birthday. He deserved a walk regardless of the weather. So on went the Barbour jacket and the faithful Borsalino waterproof, crushable…

… that’s been around the world with me.

France, 1997
France, 1997

I must have a dozen hats, innumerable caps and a helmet or two. I love them all, but they rarely see the light of day. When and how do you wear your hat? Or do you wear a hat at all?

18 thoughts on “The Way You Wear Your Hat

  1. Great post and a tough question. I did a piece on hats a while ago. I have several hats also and find it hard to be the only person wearing one. I do have a straw boater that I wear to church on Easter. The ladies love it! If they are over 70…..


  2. Hats off to you. I adore a man who dons a hat, a cap but not a baseball cap to the side. I loathe that. I love all kinds of hats, especially Straw Hats, and I love collecting hats, vintage hats from the 40’s. I have one with tiny flowers all over.
    I contemplated wearing it on my wedding day.

  3. I am one of the few people I know who routinely wears a hat, partly because I need the protection as I don’t have your bushy head of hair, and partly because I like the way I look in a hat. In the City (I spend weekdays in Manhattan) I regularly wear one in the winter, at least when the thermometer drops below 45 degrees and certainly when I know I will be spending time walking about town. I have several fedoras from crushable to more structured that regularly appear on my head. I tend to prefer the crushable, heavier felt ones since they are not as formal but still quite natty. Weekends in the country I occasionally wear a Tyrolean number with feather and boar’s bristles that I bought years ago while skiing at Cortina, Italy. Its a great favorite of mine and is generally good for a comment from passers by, not always flattering but almost always amusing. In summer I never wear a hat in the city to/fro work for two reasons: one its hot and hats trap heat even if lighter than air, and two for some reasons straw fedoras/panamas seem foppish to me when worn with a suit in the city, and retardataire. I do have a number of quite lovely straw fedoras/panamas that I wear on weekends knocking about and to outdoor parties, and their dandy-ishness works better in such environments I find. I loathe “newsboy” type caps anywhere except the country and even then only find them palatable under particularly tweedy circumstances, and only when worn by other people. Boaters I am afraid should be reserved for musical comedies or the Easter Parade and only worn with appropriate degree of irony, in my view.

  4. I think you look wonderful in the hat. Perhaps it ages you a bit but I think that is because of the formality of it. My theory on hats (and I wear glasses, too) is that it is all a matter of chutzpah, not actual looks. If you have the guts to do it, then stand tall and be proud of the fact that you are wearing what you like and feel is appropriate.

    I can not begin to count the hats I have: handcrafted felt, retro straw cloches from the 40s complete with embroidered veiling, hand-sewn French straw with velvet ribbons that tie under the chin. My grandmother’s velvet beret from the 1920s. I have 10 hatboxes and they only hold the most fragile hats and the largest straw hats.

    I rarely leave the house without a hat — especially if I am meeting friends for breakfast on the weekend and haven’t washed my hair yet. A hat hides a multitude of sins. At my office, I was known for my hats and (I may have mentioned this before), people look for me in a crowd by looking for the person in the hat.

    Of course, I grew up Catholic in the days when women had to have their heads covered and so got into hats at an early age. I have stopped men on the street to compliment them on their hats (my husband rarely wears one except for gardening and when it’s really cold). And I collect embroidered hats from Uzbekistan and some from India. They are purely for display.

    Everything about “Indiscreet” is wonderful esp. that apartment which looks so current I could move in. Best thing about the movie, “Four Weddings and a Funeral”: the women’s hats at the weddings.

  5. I love hats and have a few that I wear regularly. My summer hat is a great straw hat that can be dressed up with a nice ribbon and a pin. My winter hat is a fleece hat, but it’s “tweed” fleeces and it is just warm and cozy. I also have a dressy winter fur hat that’s perfect for freezing nights walking the dog.

  6. I would love to wear a hat and do plan on doing so. I only have two issues. I’m not outside enough (the 20 yard walk from car to lobby doesn’t really warrant the need for a hat) and, I have an enormous head. I have yet to find a hat that does not look like an umbrella. I believe I just need to find a good hatter who can tell me brim size, etc.

  7. No hat for me. I never can seem to insure my hair will withstand the on and offing without taking on a life of its own.

    You, sir, have aged exceedingly well. You make me quite envious.

  8. You look quite Madmen in your hat! Dashing, as usual. I do prefer it I think with the more casual outfit you have shown with your leather jacket. But what does one where in the rain otherwise? It’s perfect for that!

  9. my head is too big to wear hats (they never fit and i look ridiculous) BUT i love love love when men wear hats. it’s so sexy. even just a little wool cap. love. thanks for the reminder!

  10. Hello all and thanks for the feedback (and many compliments.) Ms. Goddard, never underestimate the simple Navy watch cap, it’s a classic.

    Thanks Ms. Finberg, the gentlemen to whom I refer, however, are in a class of their own.

    Fairfax, you’re cracking me up. And I hope it’s one of those Russian numbers that look as if there is an animal curled up on your head. I love those.

    katiedid, I love carrying an umbrella, but the hat is easier when juggling children, packages and the dog.

    theo, I have yet to find the stuff that keeps every hair in place. Hat head is the price to pay when you must tip your hat.

    Turling, crown hiehgt makes all the difference as well. Persevere. Courage!

    Sir Fopling, I am envious. I know you do it justice.

    ELW, I think all women should own a number of hats and employ them to great effect. “Four Weddings” is ample proof, as are you.

    Reggie, a Tyrolean! Excellent. If it was good enough for Der Bingle…. And like Mr. Lane, the boater is an Easter Sunday favourite. A conversation piece at least.

    Mrs. PvE, I, too, have several vintage hats. Very well made and a delight to wear. Or even look at as they rest on the shelf. I’ve always wanted a hat wall on which to hang them here at home.

  11. You look really good in a hat. I have a large cranium so it really isn’t flattering.

    Also, the weather killed me at the Richmond Marathon today. Hot and humid in Nov!!

  12. Hello l2r, hope you enjoyed it nonetheless. If you went down Grace Street on the way back, you passed my house. Somehow, I missed the whole thing today… kids. And yes, 70ºF is a bit above normal. Yesterday I did a few miles in 55ºF and rain.. much easier.

    The trick is finding a hat with the right proportions. Most movie stars are short and have huge heads. Crown height and width of brim make all the difference. It’s like balancing your shoulder width, collar and knot with your head when choosing a jacket or shirt and tie.

  13. You said it. A good looking hat requires balance between head, height, weather, and a host of other elements including your personal coloring.

    I have several, but I only manage to wear them in cities where and when when it’s damn cold and drizzly. When I don the Burberry’s trench, people think I’ve seen Casablanca too many times. I’ve seen many gentlemen look good, others look ridiculous. I’m still working on it, and glad you’re trying too. You’re pulling it off better than me…

  14. In reply to your implied invitation of the suitability of your cranium for hat wearing, it appears to me that in those instances where the hat looks a bit awkward, the problem is not your face or head shape but the glasses shape you’ve selected; the squarer, narrower frames pair quite well with the brim, and don’t hide your face.
    As to my own chapeau-torial shortcomings, I share with the aforevoiced fear of hat-hair; a gentleman doesn’t wear a hat indoors, and one rarely has the luxury of a mirror, a comb and a moment to fix one’s hair as one enters an indoor environment. (Perhaps the disappearance of hall-mirrors led to the disappearance of proper hats, or vice-versa?) I also will admit to the wearing of the ball-cap and visor whilst on the water and when in port; I won’t attempt to defend the practice, as my as the argument would be one of practicality and convenience rather than elegance and there are no doubt classier options.
    That said, I do have a small collection of non-ball-cap hats, among which are a few that I do occasionally wear. The watch cap is of course a cold weather standard, and the tweed “newsie” is a must with heavy sweaters or the barncoat IMHO. More interesting though less frequently put into service is the “panama” (purchased at the source in Cuenca Ecuador) which usually tops a seersucker or linen suit for outdoor summer functions. I have worn my “Tyrolean” (purchased in Merano in Italy’s SudTirol) for upland bird hunting, but I generally prefer my somewhat more mundane but well loved felt fedora (Orvis).
    I applaud the attention to proper and traditional headgear – I’ve caught some buzz about it in sartorial circles for the last couple of years, and I suspect it may fully catch on as a badge of style among those in the know within the next half-decade. Doff ‘em if you’ve got ‘em!

  15. Cap’t, well said. And well done keeping sartorial standards high with your collection of hats. Good point about the hall mirrors… I don’t even carry a comb these days. Strange to think that. I think that the automobile and garage killed the hat. Wear the ballcap! In casual circumstances, they are very useful. I tend to like red or khaki coloured ones since I don’t really follow sports and would hate to be drawn into a conversation about a team.

    I do like my art director glasses, but consider them formal wear for the most part. Hmmm, may have to rethink that.

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