Leelee Sobieski vs. Tilda Swinton, both in Jil Sander: who wore it worse?

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These are some photos of LeeLee Sobieski at last night’s “Night of Stars” event in NYC – the same event where Jessica Biel tried to steal the show in an overblown Valli gown. LeeLee is wearing Jil Sander. I’ve also included photos of Tilda Swinton at the Toyko Spring/Summer show for Jil Sander several days ago – Tilda is also wearing the designer, obviously. Who wore it worst? Is that the wrong question to be asking? I actually admire the severity and extreme editing of the current Jil Sander line. I enjoy simplicity, and I think Jil Sander separates are probably what a lot of working women need to complete their wardrobe. That being said, if the wrong woman wears Jil Sander from head to toe, it can be a train wreck.

LeeLee’s look last night was a disaster, I think. She seems to be trying to work this look straight from the runway, and the result is much, much too severe. My first thought was “Amish”. My second thought was “she’s much too young to be wearing this.” My third thought was “I wouldn’t mind having that skirt, but I would wear it differently – lower on the hips, and with a cute sweater.” My favorite part of the outfit is the pocket detail. My least favorite part is how LeeLee styled it – too blah, too corpsey.

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Now, onto Tilda. She’s so magnificently weird, so when she wears something so incredibly simple – this blah Jil Sander dress – she still stands out and looks so alien-like. Tilda has been a big supporter of Jil Sander for a long time – and Jil Sander did all of the clothes for Tilda in I Am Love.

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Photos courtesy of Fame & WENN.

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32 Responses to “Leelee Sobieski vs. Tilda Swinton, both in Jil Sander: who wore it worse?”

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  1. brin says:

    LOL@”who wore it worse”! I gotta go with Leelee for the strict prairie school marm look.

  2. Victoria says:

    i like the severe school marm look personally. not joking.

  3. Flan says:

    Always like reading about Tilda on this website.

  4. JustJen says:

    blah blah and more blah… To me, if you’re going to spend on designer clothing it should be a wow piece in your closet…that skirt, for example.

    LeeLee looks like a Sister Wife, if the sister wives could afford couture.

  5. gamblea says:

    The should switch outfits, LeeLee is too short bodied for that look.

  6. Diane says:

    Leelee just needs a bonnet to complete this outfit.

  7. gee says:

    Tilda looks nice! And LeeLee needs a softer shirt or skirts. Too severe paired together.

  8. Sweetpea says:

    I genuinely love this look on Tilda. It’s simple, but understated sexy. I like the shoes, too. But it’s a rather unfair comparison: Tilda has 25 years (give or take) and a ton of experience on Leelee. She has the gravitas to pull off this kind of outfit. Leelee doesn’t.

  9. Jessica says:

    I swear Leelee and Helen Hunt could be related!!

  10. Eve says:

    My first thought was “Amish”.

    Mine too.

  11. podzol says:

    The answer to every question in the universe is: Tilda. You’re spot-on, Sweetpea.

    And thanks for this post Kaiser :): it’s always more fun to muse about genuinely interesting characters rather than boring starlets such as Lively, Biel and their like.

  12. MJ says:

    Wow, if this can make a super-thin girl like Leelee look dumpy and kinda chunky, then I suppose it’s not for anyone. And what is with that janky tailoring at the waist? Did she do that herself while wearing it in the car on the way to the event?

    Tilda’s dress is pretty. She is so striking that something this simple really makes her stand out, rather than blend in as it would on a more conventionally pretty woman.

  13. Sasha says:

    I didn’t even have to look at the pictures to know the answer, because Tilda can do no wrong!

  14. Rhiley says:

    Oh lawd, somebody should just put a wave in Leelee Sobieski’s hair and stick her on the Yearning for Zion Ranch and let’s call it a day. That outfit is tragic. And I am confused how you would wear the skirt lower on your hips, Kaiser, cause it has already eaten her feet. Leelee gets the Bitch Please! slap of the day.

  15. ladybert62 says:

    Wow – those are like clothes I would wear to work (when I was still wearing dresses/skirts – a very long time ago).

    But – they seem wrong for a red carpet.

    Does Ms. Tilda EVER wear any mascara? She has beautiful skin and I love short hair but she needs something on her face – she always looks like she has no eyelashes!

    But at least she is not the usual hollywood type with big boobs, big butt, long hair down to her waist etc etc. She is certainly unique!

  16. ocean says:

    wow thats ugly clothing

  17. Maritza says:

    Tilda looks much better because the dress is well fitted. Leelee’s outfit looks like something Amish ladies would wear.

  18. CindyBman says:

    @ Victoria – I’m with you.

    Mock me if you will (I’m ready for it!) but I love the look! I love what Tilda’s wearing, especially.

    Maybe it’s because I am of an age (ahem) that I am old enough to remember when this was in style (high waisted, slim lines, kinda’ preppy, 80’s).

  19. Nanea says:

    SWINTON!

    That said, I like how Raf Simons stays true to the peculiarities of the JS brand. I have a dress designed by JS back when she was still the owner, and it’s similar in its simplicity. It doesn’t look dated at all, unlike ruffles, patterns, garish colors…

    Leelee looks like she made an unfortunate decision.

  20. Trek Girl says:

    I agree with Victoria and CindyBman; I like this style of clothing. I think they both look great. I especially love Leelee’s outfit.

    For the average celebrity, dresses like this would look ridiculous on them, but Tilda and Leelee have the right faces, bodies, and personalities to pull it off. They wear the clothes, the clothes don’t wear them. I think it would be the other way around for most other celebrity women, and would look like costumes to boot.

  21. Sumodo1 says:

    Tilda is pulling off the Jil Sander, while Leelee is swimming in it. Didn’t Jil Sander buy back her rights to the name? I am confused.

  22. sasa says:

    Tilda looks beautiful, I love it when she does total simplicity. Leelee is overwhelmed by her clothes.

  23. Bernice says:

    The skirt Leelee is wearing looks like a high school home ec project gone bad. Look at the side clasp on the waistband and the horrid darting or pleating of the skirt. Horrible. I like Tilda’s dress but would have liked accessories – a small narrow leather belt in an interesting colour or texture with coordinating shoes. Or some sort of jewelry – necklace and or earrings and bracelet(s). The dress as currently (un)styled is very Tildaish. Stark, severe, other-worldly.

  24. Trek Girl says:

    Something I forgot to mention in my first post is that I don’t think Leelee’s clothes are harsh looking at all. They are actually quite delicate to me. To me they don’t swallow her up or overwhelm her. I think the fit of the clothes is just right, and as Jill Sanders intended it to be. Not everything is meant to hug the body, or, on the other end of the spectrum, drape around the body like some grecian garment.

    I also must say that I like that Tilda and Leelee aren’t wearing accesories. I think any accesories would take away from the clothes and the women, and instead of enhancing the look and the beauty, would detract from them. Accesories aren’t necessary for every outfit, and it seems that Tilda’s outfits are, on a regular basis, complete without them. To add accesories to these looks would be gilding the lily.

  25. Gwen says:

    THE SWINTON works for Jil Sander. I’m not sure many other people could wear this sort of clothes and look even close to good (except for models but they don’t count).

  26. Lalala says:

    Tilda’s dress is kind of boring for her, no? Like upscale J. Crew.

    LeeLee is a disaster, but an interesting disaster. Props to her for taking a risk even if she didn’t pull it off.

  27. april says:

    Yuk. Definitely looks Amish.

  28. RuddyZooKeeper says:

    Looks like Tilda is on her way to church.

  29. DrM says:

    On Tilda it looks good…on LeeLee it does not…

  30. munchies says:

    what tilda worn is too simple for her fashion taste, something Jolie would wear actually.

  31. Angi says:

    Tilda looks really lovely. She looks very classy and understated.

  32. Hamster says:

    Give Leelee a break! I honestly liked it on her better, even if it did look a little old fashioned.

    I think maybe it was because Leelee has a prettier face and looks very young, much younger than Tilda.

    Leelee looks stunning in anything.