David Letterman debuts his Santa-esque retirement look: love it or hate it?


This is David Letterman. Seriously!!! David Letterman and his wife Regina Lasko are on vacation in St. Bart’s right now. Dave is a regular in St. Bart’s, he’s been vacationing there for years. But Letterman has been retired for nearly a year, so people are sort of freaking out about seeing his “retirement style” these days. He’s completely bald and he’s got a giant Santa beard! I personally think he looks nice. But then again, I almost always enjoy “retirement beards” and “out of work beards” on men.

Regarding his baldness… there were always rumors that Letterman wore a rug, but many are saying that in these photos, it looks like he’s gotten a buzzcut. I think that’s right – you can see that he’s got some hair growing in, so he’s not completely bald, he just buzzed his hair for his vacation, probably.

Anyway… do you miss Dave? I do a bit, although I’ve never been one to stay up and watch the late shows at any point (I’m a morning person, not a night owl). Still, I miss watching clips of Dave. I think Stephen Colbert is doing a good job, from what I can tell, but people genuinely miss Dave. I don’t think he missed it though.



Photos courtesy of Fame/Flynet.

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73 Responses to “David Letterman debuts his Santa-esque retirement look: love it or hate it?”

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  1. Canadian Becks says:

    **Runs screaming back to mommy.

    • Aliss says:

      Let the man enjoy his retirement in peace.

      • Pix says:

        Seriously. This man wore a suit every night for 20+ years! He’s entitled to look anyway he pleases while on vacation during his retirement. On a side note, I’m kinda loving the scrutiny of a man’s look for a change. The media is conditioned to tear down women if they don’t fit the idea of perfection. It’s refreshing that a man be put on the coals for once.

      • Tonka says:

        Yeah. I can’t even snark on Dave. He’s retired and enjoying time with his family. Good on him. He looks great.

    • Kitten says:

      Honestly, I plan to warmly embrace full-time slob mode when I retire so I cannot judge.

      • Lizzie McGuire says:

        I plan on wearing Hawaiian shirts when I retired so I say carry on David.

      • SusanneToo says:

        I’ve been retired for nine months and currently my fashion is more KStew than Audrey Hepburn, so go for it, Dave.

      • sauvage says:

        I plan on rocking skinny jeans and tattoos until the day I drop dead, and I will be f***ing fabulous. I also plan on being the cool elderly family friend who makes dirty jokes, and who tells her friends’ adolescent kids that it is all right to just be who you are.

        Needless to say, I’m all for David Letterman just being comfortable.

    • GoodNamesAllTaken says:

      I’m with you. You can be relaxed and comfortable without tattooing “I give up” on your head. Awful.

    • stinky says:

      he wore it for an hour tho… to be fair.
      but you make a great point anyway.

    • Lake Mom says:

      As someone who had to dress business professional every day for 30 years, the greatest joy of my retirement is jeans, t-shirts, and no make-up. Enjoy your retirement, Dave! You earned it!

  2. lisa2 says:

    Hell he’s retired.. he dressed up for years.. and kept that look on point for his career. NOW he has left that behind. This is when you do whatever you want; how you want; when you want.

    good for you David.. I can’t wait for retirement.

    • Eleonor says:

      His beard is glorious.

    • Sarah(too) says:

      Yes. Let him enjoy life. He has buzz cut his hair and stopped tinting it. He did this almost the moment he went off the air. He’s been around Indy a couple of times and people were all “Whoa! Letterman is grey!”

    • tealily says:

      It sort of drives home that men as well as women in the industry face a lot of pressure about their physical appearance. Even a guy like David Letterman, who was never a heart-throb looker!

  3. Tash says:

    I can’t hate. Ah, must be nice to be a retiree and vacationing in St. Bart.

  4. Square Bologna says:

    Walter White: The Golden Years! 😀

    • The Other Katherine says:

      I know, right?! My first thought was, “Is David Letterman on the lam? Because he is UNRECOGNIZABLE.” He actually does look more like Walter White.

      • Dinah says:

        My thoughts exactly. I wish him a wonderful, peaceful life with his loved ones. But I have to admit I was stunned when I saw David’s name associated with David’s current face, or should I say what I can make of it.

    • Who ARE these people? says:

      Walter White as ZZ Top.

    • Dangles says:

      Duck Dynasty Dave.

  5. Willa says:

    Kinda love it.

    • Esmom says:

      Yeah, I think he looks great. And up until now that we know it’s him, unrecognizable. A clever way to get out of the spotlight.

      Someone in the NYT commented yesterday that they were amazed the photographer even knew it was him.

      • ichsi says:

        I think that’s the main reason for the look. The guy has one of the most well known faces in the US, there’s hardly a chance he can enjoy his retirement in peace if he keeps looking like he did on the show.

  6. lilacflowers says:

    During this political silly season, I really miss Dave. He could do a great political interview and ask to-the-point, relevant questions and if the candidate responded with canned rhetoric, he would challenge them brilliantly.

  7. Crumpet says:

    Crap, he looks like a garden gnome.

  8. Jacqueline says:

    I bet he is living in relative anynonimity, and quite enjoying it. I never would have recognized him.

  9. mkyarwood says:

    Jennifer Garner, take note: this is how you avoid the paps.

  10. Maggie Grace says:

    What’s with his wife?

  11. Esther says:

    if he wants to stay under the radar its a good look, i wouldnt have recognized him.

  12. LookyLoo says:

    He’s bald. Hair is only growing in on the sides. Good for him for letting it all hang out. 🙂

    • Nic919 says:

      In the first pic you see really short hair on top. It starts midway on his head, but it is there. He always joked about wearing a bad rug, but since he never had super full hair on the show in the later years, it was just his hair slightly longer than it is now. He has blond hair going white and it wouldn’t be possible for him to go bald in a year just with regular aging.

      He probably is wearing the beard to be incognito.

  13. Prairiegirl says:

    I didnt recognize him, TBQH. When you’re done, you’re done, just like Johnny Carson.

  14. AlmondJoy says:

    This cracks me up and I love it! Santa swag on 100.

  15. Mia4s says:

    He seems….relaxed. Seriously though, love Dave. Dave’s father died relatively young so I think it’s great that he seems relaxed and healthy and family focused.

  16. Heather says:

    Wow. His makeup artist/wardrobe people were really holding it together.

    I’m happy he’s happy, though. He made me laugh for decades.

  17. Snowflake says:

    Love it! He probably wants to have some anonymity. Sucks people figured it out and are going to recognize him now. So much for trying to fly under the radar.

  18. Jayna says:

    I guess no one notices it’s David Letterman. LOL He gets his anonymity. He said his wife and son hates it. I can see why. I will always have a soft spot for David Letterman.

  19. canadiangirlgirl says:

    Love it!! Let the man relax and enjoy life!! Good for him!

  20. lucy2 says:

    That’s not an out of work beard, that’s a just woke up from a 6 month coma beard!
    He had a high pressure job for a long time, good to see him enjoy retirement. I was never a huge fan, but I’d imagine he’s missed in late night.

  21. sofie says:

    A minute there thought he was guy on duck dynasty.

  22. Tris says:

    I think he looks fantastic! What a brilliant way to tell Hollywood (or NY) to f-off! Funny, lovely, Dave: enjoy your life!

  23. Dragonlady sakura says:

    Holy crap, I thought that was Randy Quaid!

  24. Dick Move says:

    Bad Santa.

  25. gwen says:

    I miss watching Dave every night. Colbert just isn’t cutting it for me.

  26. Choo says:

    Looks, looks, looks. When *will* people stop being so fixated on them?

  27. Nikki says:

    95% of men over 60 look SO much better when they keep their hair trimmed close and their beards trimmed VERY short. I don’t mind the baldness at all, but the wild beard is very aging, and makes him look like he’s out of the loop. That said, I have always liked David Letterman, and wish him the best.

  28. Velvet Elvis says:

    I personally can’t stand big bushy beards like that. I’m glad that he’s enjoying his retirement and doing wtf he wants but I think he looks gross.

  29. Mrs. Darcy says:

    I mean, it’s one way to avoid being recognized, personally Santa beards, or any beards , are a no no for me! I liked his unruly mop, it softened his grumpiness.

  30. MediaMaven says:

    The man almost died from heart failure, he got a second chance, and he’s living life on his terms. I doubt anyone in St. Barts, upstate NY or Montana (where he splits his time) give a rats ass about what Santa looks like on his off-season. I know Dave doesn’t.

  31. LMS says:

    He looks happy and authentic. I aspire to be like this!

  32. hogtowngooner says:

    He looks like Randy Quaid.

  33. Drs. Fixxie says:

    IT looks sexy, and im not even drunk yet.

    Xxx THE Bday girl

  34. Misery Fox says:

    This made me realise that I REALLY don’t know what David Letterman’s face looks like… Apparently I only recognize him by his teeth and overall look? Which is so weird, since normally I am really good with faces. I did not recognize him AT ALL.

    • Dangles says:

      I once knew a woman named Misty Fox. Apparently she’s a make up artist in show business these days. Any relation?

  35. Ali says:

    Swooooooon. I would still hit it.

  36. Colette says:

    Gosh it would be great to have Letterman on the air right now making jokes about Trump.

  37. Mollie says:

    I miss him but I’m glad he’s happy.