Kate Gosselin’s Kentucky Derby style: hooker-wear or just horrible?


The Kentucky Derby was held this weekend, and that only means one thing: Americans trying to pull off British-style funky hats. In case you actually care about the race, go here to People Magazine to hear about the winner, Animal Kingdom, and his jockey John Velazquez. Apparently, people were rooting for Pants on Fire and his female jockey, Rosie Napravnik. All of this means nothing to me, because I am so overcome with revulsion at the sight of Kate Gosselin’s hideous hat. Some people just can’t pull off a hat – I am one of them. First of all, my head is too big for traditionally sized ladies’ hats. Second of all, I never go any place where I would need to wear a hat. Third of all, I dislike hats. Kate Gosselin thinks she’s a hat person, however. And what she ended up looking like is a day hooker in a budget lampshade. As for the dress… um, lace details AND horizontal stripes?!?



Other celebrities at the Derby… Kate Walsh, who was probably the most successful hat-wearer at the event. I think she looks very chic.


Paula Patton is Exhibit A in “Why Not Every Beautiful Woman Looks Good In A Hat”.


Nick Lachey and Vanessa Manillawhatever. Nick looks nice and appropriate. Vanessa looks like she was at a club and someone drunkenly jammed a novelty hat on her head.


Christopher Meloni and his wife. Meloni looks like a bodyguard. His wife looks… appropriate, I guess.


Ian Somerhalder decided he wasn’t going to let the ladies have all of the fug hat fun! Behold, Ian and his chapeau.


Photos courtesy of WENN.

You can follow any responses to this entry through the RSS 2.0 feed.

78 Responses to “Kate Gosselin’s Kentucky Derby style: hooker-wear or just horrible?”

Comments are Closed

We close comments on older posts to fight comment spam.

  1. DGO says:

    Thank you for this post! I haven’t laughed this hard in a long time. Kate Gosselin hasn’t looked this hideous since her Paparazzi fiasco on DWTS.

  2. Jennifer says:

    I honestly don’t think the dress is that bad. The hat, however, is a crime in and of itself.

  3. mln76 says:

    I love the Derby and the ridiculous hats remember a couple of years ago when the Queen came and there were bets on whether or not she’d have a feather in her hat (LOL)

  4. Rita says:

    With proper care and watering, Kate’s hat should grow into a very nice grass hut in a few years.

  5. Zelda says:

    That dress is so 90s. Also, inappropriate for day time.
    Altogether the look is very “Miss Kitty’s Muppet Brothel”.

  6. Angie says:

    The close up shows that she is as truly ugly on the outside as she is on the inside. Will she never fade into obscurity? Ugly, horrid woman.

  7. Paige says:

    Kate is a disaster. Nevermind the pathetic Whore outfit. Who invited her to my Great State anyway…they should be kicked out of Kentucky. Thanks for the post…hilarious!

  8. dr.bombay says:

    The dress & shoes aren’t bad; the hat and orange two tone hair in addition to the crispy spray tan look tacky.

  9. tmbg says:

    Can anyone attend the Derby, because if not, then how the hell did she get in? I swear I’ve seen a lampshade somewhere that looks exactly like that hat.

    On another note, no one looks particularly good except Kate Walsh. (Manillo’s dress is nice, but the hat is a little off.)

  10. Tiffany says:

    She is hideous from head to toe. Bad hat, bad attitude, bad dress, Snooki orange tan and strappy ugly heels on cankles. Reminds me of a Madam in a brothel look, minus a fishtail skirt. It’s a very complete Fail! A Saloon Madam fail.
    Very Kate, fake from head to toe, including the horsey veneers and fake hair. Ew.

  11. jc126 says:

    Funny. I like to think that whoever styles Kate Gosselin for these things totally hates her, and so tries to make her look as awful as possible.

  12. Alix says:

    @Rita: LOL!

    @Kaiser: I feel ya, honey — I can’t wear hats either — they’re all made for pinheads, if you ask me.

    The real question here, of course, is not what’s on Kate Gosselin’s head but why that wench is at the Derby in the first place (I assume she wasn’t competing).

    Meloni is the HAWTness, even in an incredibly ill-fitting suit. Wifey looks several years older than him…

  13. Amanda says:

    Kate looks ridic in that dress. The horizontal stripes over lace is one of the fugliest things I have seen in awhile.

    I don’t care that much for Vanessa and Nick, but wow- they both look great (hat aside). She has awesome legs and I’m jealous!

  14. SRM says:

    @Rita, I was thinking the exact same thing. Looks like she took the roof off of some mini tiki hut and thought, “hey, this would make a great Derby hat, so elegant and graceful!”

  15. TeeTee says:

    Thanks I needed the laugh, Mother’s day is always kinda sad for me since I lost my mom..

    I laughed really hard on this post.

    uh, no to Kate. she tries so hard though. smdh

    Vanessa, a huge NO, with the clown hat

  16. the original bellaluna says:

    Actually Kaiser, I think she looks more like the budget hooker you’d find trollin’ the ho stroll in an alley in NOLA after Mardi Gras. Or some tropical island she can’t afford to work herself back home from when a trip abroad goes terribly awry. Or Sesame Street, but why would she want a hat made of Muppet?

    And I mean that in the nicest possible way.

    @ Tee Tee – I’m sorry about your mom.

  17. Crash2GO2 says:

    Ian Somerhalder looks so much like Rob Lowe it scares me.

    Good call on Kate’s hat Rita. lol!

    Happy Mother’s Day to all the moms!!!

  18. JuJuBee says:

    Ugh, leave it to C and D-list celebrities to turn the Kentucky Derby into a red carpet event now. Kate is really desperate for celebrity, isn’t she?

  19. HotPockets says:

    @ JUJU

    That was my first thought, my god, this woman is so desperate to be relevant and famous. She wants so bad to be a legitimate celebrity. I actually respect John because compared to her, he looks sane.

    My head is so big! One size does not fit all.

  20. Marjalane says:

    Have these women in the black dresses and hats never been to Kentucky in May?! They look like they’re going to a funeral wearing an ugly hat. Kate Walsh’s dress was great, but I still hate black hats at the derby! That grisly Gosselin woman ALWAYS looks like she just missed the stylish train. I’m sure she picked that outfit out ALL BY HERSELF!

  21. Green Is Good says:

    Way to scare the horses, Kate. Yikes!

  22. DoMaJoReMc says:


  23. Aly says:

    The first think that popped into my head: She won a leg lamp from A Christmas Story.

  24. Kiska says:

    Kate looks like a cheap hooker from “Gunsmoke”

  25. wtf? says:

    this women thinks she is all that and in reality she is not.

    go home, be a mom again to your 6 very confused children and stay away from the cameras.

  26. original kate says:

    LMAO at kiska! you’re right, though – all she needs is some guy playing the piano and a set of swinging saloon doors.

  27. SoCal says:

    Wow, I thought Kate was Beyonce for a minute…

  28. girlygirl410 says:

    I am ready for the shots…

    I like Kate, she does not give up.

    She looks bad and needs a stylist, the hat sucks. Her body is great, make-up is good for the party/dress.

    She has a ton of kids and needs to make money. I like that she puts herself out there to provide for the kids.

  29. wunderkindt says:

    Hey Kate, you’re a bit late for that Royal Wedding!

  30. heb says:

    Kate’s dress would look a lot better without those fug stripes. Her face is looking pretty beat these days, he he.

    It annoys me when people 1) wear hats that don’t match their outfits and (Paula Patton) and 2) wear black to the Derby (Vanessa!!!! come on!!! plus it looks bad next to Nick’s suit!)

  31. bluhare says:

    I love hats and I wish that they were more fashionable. I can wear hats, and I would die a happy woman if I had an event to go to where I could wear one of those fascinator thingys. It would involve a black dress, netting, lace hanky, and dead rich husband.

  32. Lisa Turtle says:

    I feel very sad for Vanessa Milano. Even if she and Nick have a great relationship, it will always be overshadowed by 98 Degrees & Newlyweds & Jessica Simpson. The fact of the matter is nobody cares who Scott Baio ended up with, Joanie <3s ChaChi 4Ever.

    Yes, to close friends and family it won’t matter… That’s what they will tell themselves.

    But everytime they meet someone new it will come up. Inevitably. The questions will be asked. Maybe not right away, and not always to their face, but the whispers will always come back to one topic. They will spend their lives in the shadow of Nick’s baggage. And that is very sad.

    This is probably how it is for any minor celebrity who dates someone exceptionally famous. Even Chris Martin says its embarassing to always be compared to Brad Pitt. Even Chris Martin feels shadowed!

    But this is what it is to be a celebrity, you sell a little piece of yourself – a photograph, a video, a story – and now people know that about you. It’s part of the popular consciousness. When all the consumers of pop culture see someone who had their flicker in the spotlight, they can’t help but wonder “Hey, what was it like to be married to Jessica Simspon?”

  33. Chrissy says:

    Kate’s hairstylist must hate her … that color looks AWFUL under the hat! Perhaps she was trying to cover a really bad dye job??

  34. flounder says:

    lol, I love kaiser’s comments on every photo. Just hilarious.

  35. Magsy says:

    I thought hats were to be worn by the women, not the horses.

  36. truetalk says:

    kate gosselin looks like she has a small creature
    perched on her head;maybe a porcupine?

  37. Amy says:

    wait… what is that? It vaguely reminds me something a French marquis would wear… or something out of the 3 Musketeers! Some member of European aristocracy.

  38. Cheyenne says:

    I can’t stand hats and never wear them but I want Kate Walsh’s and Vanessa whats-her-face’s shoes.

  39. Nanea says:

    Hooker wear, hooker nails, fake tan, fake smile, ugly demeanor – I had totally forgotten that one was still around.

    Her poor kids, they must be scarred for life with such a mother.

  40. Blue says:

    Lmao @ Magsy

    I don’t think the dress is awful ( i’ve seen worse). That hat is beyond words. Yuck

  41. DetRiotgirl says:

    I think it’s hilarious that the title of this article asks if she looks like a day shift hooker or if she looks horrible as though looking like a day shift hooker is the better of the two options. Haha, that hat… Thanks for the laugh!

  42. beebeedoom says:

    Wow @ Lisa, you’ve really put a lot of thought into that huh? I doubt these couples care as much as you.

  43. bagladey says:

    Kate Gosselin – UGH!

  44. harfang says:

    Oh. dear. GAWD. To me this is actually a bit sad, because when done right, the dark-lace/flowers/whatever-over-mauve thingy (you can see it, looking somewhat cheap but relatively unadulterated by prison stripes, on Gosselin’s ta-tas) is a fun Victorian/nouveau motif that can be sexy or just nicely vintage.

    That skirt needs an enema.

    I respectfully disagree with you, Kaiser, about Patton; but of course I agree about the Man-Fug and the Millivanilli lady.

  45. Anastasia says:

    Ug, I had totally forgotten about that woman. Let’s go back to that, shall we?

  46. kc says:

    Kate is beginning to look like Dina Lo.

  47. Amanda G says:

    Kate’s dress is okay, but the hat is awful. I like Vanessa’s dress a lot. Ian used to be hot, what happened?

  48. SassyOne says:

    Head to toe fail.

    When will she ever go away?

  49. skilo says:

    Ugh. I can’t stand Kate Gosselin. That dress is awful on it’s own though, so is the ridiculous hat that reminds me of a bad lamp shade.

  50. Maritza says:

    Everyone looks fabulous! I love the hats and outfits, very appropriate and pretty.

  51. Abby says:

    I am from Lou and attended Derby. On Friday (Oaks day at the races) everyone you have pictured here looked much better. Hats are huge at the races here, I know these may look bad to most, but there are some ridiculous hats worn.

    Marissa Miller looked awesome if you can find a pic of her both days. Of course she would look great in a potato sack too. Vanessa looked very pretty as well IMO and very approachable and sweet.. They’re were some major hot guys there this year too!!

    I was actually surprised how pretty Kate G is in person, I don’t like her, or what she represents….but she is very pretty in person.

  52. sandip says:

    Please make Kate go far far away. I think Paula Patton looks cute.

  53. Samigirl says:

    Kate looks terrible. That hat is absolutely terrible, but I can’t believe nobody has said anything about that thing under Paula Patton’s armpit…it looks like a teensy vagina.

  54. Debsa says:

    Horrible inside and out.

  55. cannonball says:

    I’m a star.
    I’m a star. Just look at me in these star clothes with a huge star hat! I did it.

  56. Um. . . shouldn’t she be spending mother’s day with her kids?

    I mean, I’m not begrudging moms a day off every now and again – but when you make millions of dollars selling an image of yourself as an ideal parent (to say nothing of selling your children!). . .
    Just seems strange, is all.

  57. Ronobo says:

    Who is this person? Why should I care about their hat?

  58. jill says:

    the age is showing in the neck. can’t hide those wrinkles.

  59. Vicki. says:

    She’s not pretty enough to pull off a hat, or the over the shoulder smolder or the dress. Well you get my point. Spray tan & highlights does not make one pretty. Oh the snob in me…..

  60. neelyo says:

    When I saw the header photo, I thought it was Lindsay Lohan which I guess is a compliment to Kate Gosselin.

  61. dorothy says:

    Why on earth is this woman even on this website? Is she famous? no. Is she popular? no. Is she a celebrity in any right? no. Again…why is she featured here?

  62. ladybert62 says:

    Wow a living breathing “surry with the fringe on top!” HIDEOUS!

  63. Sheigh says:

    A festival of laughs!

  64. Samigirl says:

    There is another picture of her at the gifting suite. The new hat/dress combo is better, but she’s wearing the exact same fug shoes. Whatever. She isn’t relevant. And I agree with @missyaggravation. I certainly hope she jetted back home in time to spend mothers day with her children. I had to use legal action to get my son on Mother’s Day, so to see a woman not caring about it would truly piss me off.

  65. TXCinderella says:

    And why is Kate Gosselin still relevant as a celeb? Her 15 minutes were over when she split with Jon. No one cares anymore! Vanessa needs to get a clue. That dress is too short for the KY Derby.

  66. Judy says:

    For anyone interested, there’s a video on Radar of Kate and loverboy Steve at the Airport yesterday morning.

  67. bondbabe says:

    I thought the headshot photo of Kate was actually Chelsea Davey!!!! (Which is bad for both of them….)

  68. Testarosa says:

    I vote hooker wear AND just horrible. Am sorry to say, though, that Kate could probably only get a gig as a Madame. Not aging gracefully, that one.

  69. Kim says:

    First off what in the world was she doing there. Second she looks like a cheap Atlantic City hooker. Totally inappropriate for a daytime event (or any event for that matter). This woman can not dress but ill give her a pass since she isnt a celeb and has no dresser/dresses herself. She just has terrible taste unfortunately.

  70. anne_000 says:

    whenever i see kate gosselin in something or someplace expensive, i think “poor kids. there goes your college funds.”

    there’s no way in hell kate is going to be able to use that hat somewheres else. it’s a one-time use hat.

  71. sharon says:

    She looks like a $3 hooker. She is a classless, tasteless, grifter, who is reviled by millions of people. People need to stop watching these reality shows and making people like her celebrities….The dumbing down of America, making a sorry-assed Mother of 8 rich. She has nannies, maids and housekeepers keeping the kids while she runs around with her ‘bodyguard’ acting like she’s a star. What a farce.

  72. fritanga says:

    Hilarious. Gosselin actually thinks she’s a great celebrity whom everyone admires and envies. To call her delusional is just too obvious. And she’s outdone herself here – in a sea of D-listers, she’s the no-class, tasteless champeen.

  73. cakester says:

    Okay, in that second picture, Kate looks exactly like my super-skanky stepsister. *shudder*

  74. Just Me says:


  75. Pia says:

    Kate looks horrific. Her hair, skin, make-up… just ewww. And as brutal as the hat may be, wearing that ghastly frock –in the daytime no less– is beyond the beyond.

  76. Deb says:

    @Pia: The makeup is horrendous! Her lip, cheek, and eye color practically the same shade as her spray tan. Rather then accentuate her features, she gave herself a wrinkled mannequin face.

  77. cash says:

    Heya i?m for the first time here. I came across this board and I to find It truly helpful & it helped me out much. I hope to present one thing again and help others such as you aided me.

  78. aviation says:

    It’s perfect time to make a few plans for the long run and it’s time to be happy. I’ve read this post and if I may I wish to recommend you some fascinating issues or suggestions. Perhaps you could write subsequent articles relating to this article. I wish to learn more issues about it!