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Wednesday, January 22, 2025

A Question for the Community: Who are the television characters with the preppiest wardrobes?

 A question for the community:

During this winter storm, I was rewatching some Cheers episodes and had forgotten how great Sam Malone's (Ted Danson's) wardrobe was.  Boat shoes, blue boat shoes, striped surcingle belts, khakis, rugby shirts, argyle socks, tweed jacket with leather patches, bright green Shetland crewneck, even what looks like a Sero shirt.  

Which all begs this question for the community.  Who are/were the preppiest TV characters? Or at least had the preppiest wardrobes?

 

  



 

  

85 comments:

  1. Most of the actors from Midsomer Murders and Murder She Wrote.

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    1. Midsomer Murders? I've watched all of the episodes with John Nettles as Tom Barnaby and the repeats but can't recall a Preppy character.

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    2. Not preppy per se, but tons of English country attire in those episodes....tattersall shirts, Shetland sweaters, Barbour vests and jackets, corduroy pants, etc,

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    3. You could say that about several British crime series - Poirot, Miss Marple, Foyle's War, Shetland, Inspector Morse etc. The best dressed character, for me, was Hugh Fraser as Captain Hastings in Poirot. Another style hero was Sir Alec Guinness as George Smiley in the Tinker, Tailor, Soldier, Spy television series. Traditional British clothing was stylish long before Peter York’s invention of the Sloane Ranger and “Preppy".

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    4. Excellent comment about Hugh Fraser as Captain Hastings, "battler" as his chums joked about him, as in "battler of Hastings".

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  2. The “Great White Sammy”, love it. Personally would vote for Frazier. Maybe even Norm who had great collar role.

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  3. It is funny this was mentioned. I watched Cheers in their original and in repeats and always thought the same about how Ted Danson dressed. I thought it did not project the image the show was trying to project. I am not sure what I expected. Maybe his dress was a node to his high school alma mater. Good question and I am looking forward to the responses. I do not watch much TV so I can not contribute.

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  4. Sam Waterston as Nick Carraway in the 1974 version of The Great Gatsby'. Sam was a Groton alumnus.

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  5. Two a bit dated, but… The Patty Duke Show and Fred MacMurray in My Three Sons.

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  6. Otter and Boone in Animal House.

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  7. Wow, I never noticed, but Sam Malone is a great call. I'd argue Seinfeld's George Costanza is a stealth style icon. His style isn't preppy per se, but it definitely has Trad and Ivy cues. Lots of button down collars, khakis, plaid shirts, Earth-tone odd jackets, knit ties, Barbour-style coat, cardigans, etc. As the kids might say, "morning mist" is a vibe (IYKYK).

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  8. Well you would have to include Woody's wife Kelly. The preppiest of all

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    1. Also, the greatest sitcom song of all time "Kelly, Kelly, Kelly, Kelly, Kelly, Kelly, Kelly, Kelly, Kelly, Kelly, Kelly, Kelly, K-E-L-L-Y. Why? Because you're Kelly, Kelly, Kelly, Kelly, Kelly, Kelly, Kelly, Kelly, Kelly, Kelly, Kelly, Kelly, Kelly, Kelly, Kelly of mine. Mine, mine, mine, mine, mine, mine, mine, mine, mine, mine, mine, mine, mine, mine, mine, mine, mine."

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  9. The Friends sextet... well maybe the guys not as much.

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  10. I'd definitely say Spenser in Spenser: For Hire.

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    1. Spenser: for Hire was filmed in Boston and during that period Robert Urich (Spenser) lived in a home on the edge of the Phillips Andover Campus.

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  11. And also Jack McCoy (Sam Waterston) in Law & Order. That Barbour! I once ran into him in NYC and he was wearing the same Barbour he did in the series--clearly his own.

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  12. My immediate thoughts were Martin Sheen as President Bartlett and Rob Lowe as Sam Seaborne in The West Wing. But they wore point collars rather than button downs.

    For a movie character, Matt Damon as Tom Ripley was very Preppy. Clint Eastwood dressed Preppy as Dirty Harry but his character was anything but!

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    1. I think Freddie Miles from "Ripley" was even preppier than Tom.

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    2. Dustin Hoffman as Benjamin Braddock in The Graduate. Art Garfunkel as Sandy and Jack Nicholson as Jonathan in Carnal Knowledge.

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  13. I may be in the wrong ball park here as it's not anything to do with New England or even the USA but Brideshead Revisited with in particular Anthony Andrews as Sebastion Flyte. Very preppy in my opinion

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  14. Stephanie, played by Julia Duffy on NEWHART (Vermont.)

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  15. Hope Lange in The Ghost & Mrs. Muir.

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  16. Preppy on screen? watch old movies. The Philadelphia Story, a classic. almost anything with Cary Grant, Grace Kelly, Katherine Hepburn. A little more modern, quite a few characters Paul Newman played. Other movies: The Paper Chase, Metropolitan, Trading Places (Winthorpe went less prep as he descended). TV...Mad Men, Bob Benson in particular, but Pete Campbell and Don Draper were still often very preppy.

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  17. Anything by Whit Stillman.

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  18. Are you all kidding? The OBVIOUS and CORRECT answer is: Thurston Howell III !!! [ But not his wife, Lovey ... ]

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    1. No, that’s dressing like Palm Beach. Far far from preppy.

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    2. Wait, are you implying that a sitcom caricature of the "wellborn" is not the "real" preppy??? Well, I'll be damned... And, thank you, sir!!!

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    3. Logan Huntzberger is that YOU??? Finn? Colin?

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  19. Television person, not character, but let me suggest The Reverend Fred "Mister" Rogers. HIs iconic sweaters were made by his mom, and one can quibble his fondness for tab collars/tie bars, but...Dartmouth and Rollins. The canvas shoes he changed into at each episode start were Sperrys. Otherwise, classic, high-quality, unassuming, non-attention-grabbing tailored clothing... and he long kept a home on Nantucket. The essence of stealth prep. And, yes, character-wise, Newport's own Thurston Howell III!

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  20. I see in the comments that not everyone has the same definition of "Preppy". Some people see "preppy" with a British tweed accent, close cousin of the American "Ivy Style" and his younger brother "New England Prep". I put the Sam Malone character in the "New England Prep" bracket since he never wears a suit. If he had to, maybe he would wear a wool blazer from his Dad's closet with a flannel shirt, no tie, boat shoes and khaki's. If we are talking about "Preppy" in film, the prep that I grew up with, Preppy as in the "Official Handbook", then the film that most embodies this aesthetic would be the 1988 Rob Lowe/Meg Tilly film "Masquerade". Fans of the "Official Handbook" should watch the film and see how many times it references the book. "Masquerade" should be the "Official Preppy Movie".

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  21. Sam Waterston as Assistant D. A. Jack McCoy on "Law and Order".

    Pure style.

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  22. George Constanta in Seinfeld was totally preppy although he did not have a preppy physical shape.

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    1. hadn't thought of him that way, but really a great call on your part.

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  23. Cheers again: Shelley Long's Diane Chambers comes close. Fresh out of Bennington & BU; a touch of Locust Valley Lockjaw; waitressing for Sam Malone et al.

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  24. I cast my vote for most of the characters on The Dick Van Dyke Show in the 1960s.

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  25. How about noted sixties ad executive Don Draper?

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    1. The whole show was about self-invention of Don Draper - Pete Campbell and Ken Cosgrove were born to it, Don Draper learned how to exploit it.

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  26. Leslie from Newhart!

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  27. Jami Gertz as Muffy Temperman in Square Pegs. Although, her character was a bit over the top, her clothes were beautiful and classic.

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  28. All Creatures Great and Small. The recent series.

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    1. Typical pre-war British country clothing - decades before Preppy.

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  29. Most of the cast of the West Wing, and Carlton Banks in Fresh Prince definitely deserve an honorable mention :-).

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  30. Alex P. Keaton from the sitcom Family Ties.

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  31. What are "television characters"? ???

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  32. I would say none. Television does not understand preppy. Most of those named above require a real stretch. Certainly not Ted Danson in Cheers -- remember, that series began at the tail end of the preppy era when some of that clothing was (for a time) in the mainstream. He may have worn some preppy clothing but more or less by accident -- and certainly not in a preppy way. (The hair alone rules him out.)

    Wrt to movies (not that you asked), Whit Stillman's are the only that present authentic preppy characters and clothing. The clothing in many of Woody Allen's films is beautiful; not preppy, but classic, and much to be admired.

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    1. Concur with Stillman. Interesting pedigree, especially Charles Stillman, South Texas.

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  33. "Dobie Gillis", but it was the 1950's, so that was the "in" style.

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    1. Certainly NOT Sam on Cheers. Can't believe I have to say this here of all places, but wearing a costume does not make a preppy. Dobie Gillis is a good answer.

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  34. Charlie Sheen and John McGinley in Wall Street. Early in the movie Sheen’a character sports a great wardrobe. As he gets drug further into Gordon Gekko’s world his clothes become a little more slick

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  35. The preppiest character on TV that I recall is the presenter of the old Mousterpiece Threaer—George Plimpton

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  36. Anyone but Ed Norton of The Honeymooners. Ralph wore a tie.

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    1. You’re probably right. But might not Ed’s hat be labeled “shabby chic” prep?

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  37. “The Chief”, Ed Platt from Get Smart. OCBDs, rep or paisley ties, 3/2 roll jackets, often in a tweed.

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  38. Jason Bateman, David Hogan (The Hogan Family)

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  39. Replies
    1. Dr Seth Hazlit was always Ivy League but not preppy.

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  40. Brantford Winstonworth, https://www.youtube.com/watch?v=Nqg01Nk3SYI

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  41. "Do I get chicks? yes. Do I play lacrosse? yes. Do i get chicks because i play lacrosse? No. I'm very affluent". Brantford Winstonworth 2009.

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  42. Replies
    1. Finally! That was true preppie. Hell, it was his nickname!

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  43. The Drummond Family from Different Strokes Sitcom

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  44. More recent one...Alan, Jon Cryer from "Two and Half Men", polo shirts, plaid button down oxfords...

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  45. "YEH BRO I WAS GONNA PLAY ON THE D1 TEAM BUT THAT'S MAD WORK" Bradford Winstonworth 2008

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  46. Cheers was before my time so I can’t comment much there. I agree with others that mentioned George “Can’t Stand Ya” and Jack McCoy as well as much of the cast of West Wing. Many of the law based shows have at least one character (ie Carey from The Good Wife.

    I think if I had to pick one though it would be Richard Gilmore from Gilmore Girls. He’s often seen in a Yale Alum Sweatshirt or ballcap when not in a proper suit.

    JM, VA

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    1. Yes! I was reading this list and thought - dare I mention that many of the characters on Gilmore girls are very prep? Logan, Emily, Rory(ish). And of course the iconic Richard.

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  47. Henry Francis on Mad Men. Sheriff Andy Taylor on weekends, Capt. Frank Furillo on Hill Street Blues, Richie Cunningham on Happy Days, and yes, Steve Douglass on My 3 Sons. JDV

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  48. I think that some, if not most, of you may be confusing "preppy" with "clean cut." Furthermore, Sam Malone was handsome and charismatic and an ex baseball player, but sorry, not preppy. George Costanza??? AHAHAHA ... a neurotic and anxious nebbish and the antithesis of preppy. I mean my god ... do you remember his parents? The apple does not fall far from the tree .... :: sighs ::

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    1. The question is with regards to preppy wardrobes not necessarily WASPY characters

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  49. "My housekeeper in Darian and her housekeeper in Rye were sisters. I mean, its a small world." Bradford Winstonworth 2009

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  50. Ryan O’Neal in Peyton Place

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  51. There was a scientist on the SETI team in the film "Contact" that I recall was quite preppy to the point of wearing what appeared to be a proper BB 'Go to Hell' ocbd. I wish I could online search better to provide a link to images.

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  52. Dr. Richard Kimble (David Janssen) of '60s tv series The Fugitive: A Cornell grad, Kimble always reverted to a herringbone tweed jacket, khakis, and a white OCBD with a perfect collar roll, probably picked up at charity shops, when on the road.

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  53. The professor on Gilligan’s Island

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  54. Not preppy but certainly Tweedy- both the new and old versions of All Creatures Great and Small.

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