Friday, February 15, 2019

Reader Question: What are Preppy Hats? (Real, not Cosplay)


A question:
Avid reader of SWNE, thanks for all you do. 
My question is thus: 
I am wondering what male headwear is most appropriate for preppy dress? In the winter I generally wear a tweed flat cap and in the summer a "dad hat" baseball cap but they always seem a bit off. What would the community recommend? 
Thanks!

26 comments:

  1. In the winter I wear a collection of Irish Tweed hats from Hanna Hats, I find they are stylish, go very well with my overcoats and are very warm. for summer its usually one of my golf hats.

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  2. Very funny, I was wearing a tweed Borsalino flat cap for the commute to and from the office today, and now presently wearing a "dad hat" at the library lol. I personally think the "dad hat" is fine if of good quality, and extra points for emblems denoting clubs, associations, alma matter, etc.

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  3. What would you like the hat to do? Keep you warm? Keep you dry? Keep you shaded? Cover your bald spot? Show off your membership(s)? Appropriate is as appropriate does - apologies to Forrest Gump.

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  4. I agree with Fred, above. I wear an Irish Tweed hat in the winter, with a suit or casual clothes. In spring and summer, I wear a bucket hat (with my club emblem).

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  5. I have at least 12 tweed flat caps. In Texas, they are about as preppy and different as you can get.

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  6. Anything you want that is appropriate to the level of formality of your clothes, the activity, and the weather, so long as you wear it with the front in the front. If your wife says you can't wear it, don't wear it.

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  7. Winter: Trilby, tweed flat cap, “Stormy Kormer”, various knitted ski hats
    Summer: Panama, Tilley

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  8. Sorry to say that if you're talking preppy, it's the baseball cap hands down. In all sorts of weather. Maybe a sailing/sun hat, a la Gill or Musto or Tilley. I would classify stuff like tweed caps to be more classic or traditional or Ivy but not so much preppy.

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  9. "Gentleman's Gazette" on Youtube has at least six videos on hats. I would suggest you start with "How to Get The Right Hat for Your Face Shape & Body Type - Fedora, Panama Hats, & Felt Hats For Men" as it is based on vintage drawings and information that people just don't know anymore. My husband found it very helpful to narrow down what looked the best for him when ordering online.

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  10. Wear whatever suits the situation, but take it off inside. A gentleman never wears his hat indoors. The hat itself is utilitarian.... the doffing of it to a lady, the removal of it when speaking to an older person, a person of distinction, or someone of higher rank will show your breeding. (ie. knowledge of dress code.). I would argue it is not the hat that is preppy, because a prep is going to wear whatever hat needs to be worn, but rather that you deal with which ever hat you happen to be wearing in a gentlemanly manner.

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  11. A Red Sox cap or a cap of your "hallowed alma mater."

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  12. I'm not preppy in any way but cannot understand why adult men would wish to wear baseball caps. Those with logos on the front are especially hideous.

    In winter, I wear Garforth tweed and corduroy flat caps from Cordings. I also have a Harris tweed trilby from James Lock in St James's, London.

    In summer, I wear generally linen flat caps. A cotton or linen Trilby is the automatic choice for the club and social occasions. For sport, sailing and on the beach, a Tilley gives unbeatable protection.

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    1. Baseball caps do for the rest of us exactly what they do for baseball players: keep the sun out of our eyes and the rain off our glasses. One of the best stupid photos I ever saw was of a man with both hands cupped above his eyes at his eyebrows to keep the sun out of his eyes, while he wore his baseball cap backwards.

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    2. Do you think that those who watch other outdoor sports in summer don't need to keep the sun out of their eyes? You seem to advocate wearing baseball caps simply because they are better than nothing, a bizarre argument to say the least. A linen flat cap and trilby will do the job equally well but with much more style and panache. A linen hat will keep your head and forehead cooler.

      Cricket players still wear flat caps but, sadly, tennis players and golfers have switched to baseball caps. Baseball caps now rule simply because they are much better for advertising sponsors' garish logos. Can you imagine Walter Hagen, Gene Sarazen, Sam Snead or Ben Hogan wearing baseball caps on the course? I can't.

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    3. Sorry, but the smaller brims on flat caps are not nearly as effective as the larger brims of baseball caps either for keeping the sun out of your eyes or for keeping the rain off your glasses. They aren't even close. Fashion vs function appears to be the choice.

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    4. Dave, I can also testify that driving a convertible top-down calls for the longer bill of a ball cap. I tell people that the scar on my nose is from a hang-gliding accident, rather than the skin cancer cutting.

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    5. Are you aware that it's possible to buy flat caps with brims that are as long as those on baseball caps? It's also possible to buy linen and cotton fedora's that provide even better protection, especially for the ears. Then there are the Australian cattleman hats and safari hats, not just Tilley's, that provide great protection in the bush and desert.

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    6. Best hat for all around sun and weather protection is probably a cowboy hat, if that were the question. I expect that is the reason cowboys lived in them. Like an awning on your head. But preppy? Not up north I don't think.

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  13. No hats at all here, with two exceptions: (1) hiking (for which a boonie hat is it) and (2) winter (whatever fits the weather, usually a watch cap).

    That's it.

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  14. I'm a visor-wearer in the deep South. Much cooler than a baseball cap. And I'm referring to the thin tennis visor, not a golfers giant Tour Pro visor.

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  15. In a word....: Tilley

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  16. No baseball caps please. To the office in the fall and spring I wear a grey fedora with a black headband. In the summer I wear a straw fedora or a boater.
    In the really cold winter I will wear a black knit cap to cover my ears. Always take your hat off when inside.

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  17. Dave, that backward baseball cap story - Hilarious! :-)

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  18. Can't go wrong with a Master's Golf cap the ones with the date! College caps SEC schools a plus! They're known for great football! Any Ivy league schools also! Please no MAGA hats they're vulgar!

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  19. Good old bucket hat such as Spalding wore in Caddy Shack, or a Filson bucket in cooler/wet weather.

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  20. Winter hat: a red "watch cap" with a PENN logo that I can pull over my ears for walking in the city (comb in pocket to recover). Tweed "riding" cap from Orvis when it's not all that cold. A PENN or Hinckley baseball cap to keep the sun out of my eyes or reversed when sculling to keep from getting a sunburned neck.Usually no cap or hat at all in warm weather.

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