Better Played, Kristen Wiig

The bad news:

Gwyneth’s cape is contagious. And few but GOOP can master it.

The good news is:

If it’s okay with Hamm, it’s okay with me. Bonus points for matching your dress to your drink.

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Comments (50):

  1. Victoria

    She reminds me of the gal who played Chloe on “24″ in these pics.

  2. vandalfan

    Does she hate her waist? The rest of the look- color, hair, makeup, handbag, arm candy, is excellent, but her waist is MIA.

    • Mahastee

      I so agree, she is in desperate need of a belt with this.

      Not loving the shoes.

  3. Eliza Bennett

    She really is such a pretty girl. I love that color!

  4. Kat

    What’s sad is, she looked so good (and was friggin’ HILARIOUS) as Cinderella in the Disney Housewives sketch.

  5. La Fifie

    OMG this is dull, dull, dull! She could be a real knockout if she wanted to, but it’s as if she’s going out of her way to look dumpy.

  6. theotherjennifer

    cocktail matching is fun! Love her clutch but hate the baggy dress with the jacket over the shoulders – is she channeling my nana??

  7. Kit

    that dress is a sack! Why is it hanging off her like it’s two sizes too big?

    Oh, wait.

  8. Stefanie


    Does the fact Jon Hamm drinks girly drinks throw anyone else off?

    • Karen


    • Oh Dear

      I’m sure I read once that his favorite drink is some very girly cocktail… and he’s man enough to be proud about it.

      • Anne B

        From what I hear, his “official” drink is “Scotch”.

        But his secret passion is the Midori Sour. Which I find (like everything else about him) absolutely adorable. <3

    • McRathburn

      Srrriously don’t care.

    • Kelly O

      Jon Hamm could drink rubbing alcohol and I would consider its advantages.

      +1 to this dress for not being nude or any variation on that color.

  9. Kate

    Is it just me, or does she always look totally stoned??

  10. TereLiz

    LOL, what’s her left hand in pic 2 doing? ;)

    Great color on her, but yeah, kind of shapeless.

  11. TaraMisu

    Oh the color is fantastic! Too bad it’s a pretty colored sack. Ugh.


  12. Miss Tee

    Those shoes are making me gag.

  13. Sajorina

    This is the same old shapeless sack she always wears… BORING! Dress, jacket, clutch, shoes, hair & makeup are all BLAH & SAD! The only good about this is Jon Hamm!

  14. Designer Clothing

    Great colour!! Love the bag too!

  15. GFY Heather

    She looks hammered in these pics, which I find amusing.

  16. missdove

    I would cut a b!%*# for that jacket or the shoes. The dress doesn’t fit her, but she could save it if she belted it at the waist and bloused the top over. If she did that, we probably wouldn’t be looking at a picture of her with Mr. Hamm though, so well played.

  17. Sandra

    1. That’s not a cape. It’s a white jacket draped over her shoulders. It doesn’t make it any less offensive, but it is not really GOOP-ian.

    2. I swear that dress went down the runway at Bedford Hills Fashion Week.

    3. Ms. Wiig, hair brush. Hair brush, Ms. Wiig. You two run along and have a good long chat.

  18. that girl

    Great color, but she looks like a grandma. That dress desparately needs to have a belt added and about 24″ cut off the bottom. Replace those shoes and possibly burn them.

  19. Nicola

    Ugh, on what planet is this better played? I agree, at least it’s a colour but the shoes are HORIFFIC, the clutch clashes (and not in a good way), the dress is not even a dress. A dress has shape or cut or something. This is a burnt orange mumuu with orthopedic (sp?) shoes.

  20. Alix

    Everything’s better with Hamm.

  21. Anne B


    \#swoons #dies

  22. mary lou bethune

    She needs some satorial help and maybe he’s the one to do it. He looks gorgeous…..

  23. Mitzy Carter-Penley

    Are they dating? Cause that would be kind of awesome and explain why he is on SNL ALL the time. They should just make him a cast member. Maybe he can show her how to buy clothes that fit then.

    • Jessica

      Nope, he’s been with Jennifer Westfeldt for like 12 years.

      • neiges

        Ant that makes him sexier like dating contract girls makes your assistant Clooney creepier.

  24. What what

    At least she’s wearing a color? She’s getting somewhere.

  25. Sophia Loren

    I love this dress and the cool casual style of the girl who wears it. I also like the shoes, but don’t care for them together.

    And the jacket ruins the look of the dress.

  26. neiges

    I am sorry. I have read all the comments but my mind keeps shifting to that Hammmmlishious man. What were we discussing? Oh, grandma dress.

  27. Caroleena Stantonova

    Her adorable tangerine clutch is the only redeeming quality of this ensemble, if you will. Are her mirrors broken?????

  28. Julie

    Is it just my computer or is there a stain on the left side of her dress just below the “neck tie”? Her clutch looks like a plastic hamburger in the second picture. Why was I looking at the clutch when JH is sitting besides her? I have no idea.

  29. Julia

    Those drinks look like Manhattans to me, which seems totally appropriate.

  30. Marisa

    someone really should stop her from wearing her thrifting finds out on the town, save them for those days that you have to do a quick run to safeway or the butcher shop

  31. Jo

    She looks much better as a brunette but sack is a fail tho colour is great.

  32. Girlin

    Hate the jacket on the shoulders and the shoes but the colour is lovely on her and her hair looks good too! =)

  33. Timberlina

    Is there room for Hamm on your staff? Or would Intern George get jealous?
    I think every office should have it’s fair dose of Hamm-related products.

    (I’m not even going to comment on Wiig. It makes me sad that she’s passing up this opportunity)

  34. merciblahblah

    I have a complete girl crush on Kristin Wiig, so I don’t mind the dress – I’m just thankful she’s wearing a COLOR. Also, in the second photo, I looked at the bag in her lap and thought – why does she have a tiny hamburger on her lap? Then I realized it was her clutch. Durrrr. As for Hammmmm? Hammmmina hammmina hammmina……

    • katkin74

      ^ YES! I too thought of a tiny hamburger. hmmm….what does that say about us?

      This girl has a great face but she can’t dress herself to save her life. Everything she wears is blah, straight out of a Newport News Catalog.

  35. Daniela Fuentes

    I don’t watch Mad Men thus I didn’t know who John Hamm was till you started mentioning him. Last night I dreamt I had an affair with him…I think he’s my new crush, and I blame you!