Leelee Sobieski, Sept. 1999
At this point, Leelee -- here at the Emmys -- was a nominated actress for Joan of Arc, and had done Never Been Kissed and Eyes Wide Shut. She was only 17 years old, which may explain why her dress looks like a magic carpet. I always thought Leelee looked like Helen Hunt, but if you imagined this dress all black, don't you see a little bit of a pointier Jennifer Lawrence? I swear to God, she would've been in the Katniss mix if Hunger Games had been an older book, and that would've probably annoyed me, because to me her acting was kind of cardboard. Anyway. That is neither here nor there.
Leelee Sobieski, July 2003
What do you do when you are three years removed from Here On Earth, and Joy Ride and My First Mister and The Glass House all sort of flopped and you don't know where you're going? Three little words: camisole, bra, cape. And then five more words: tiny little blue barbell earrings. And then one more word: Yikes.
Leelee Sobieski, January 2004
I would love to share a story about how I remember when this was really in, but unfortunately, I cannot confirm that this was EVER in. I mean, I guess v-neck sweaters were, and so were throw pillows, and dust ruffles, but very rarely TOGETHER unless you were really bad at doing laundry.
Leelee Sobieski, April 2004
Two things: First, Leelee wore this to a Heatherette fashion show, and yet this is about 99 percent more coverage than anything Richie Rich has ever designed, to the point where he might mistake her for a throw rug. And second, that scarf has a neckhole. It is a poncho-scarf-blanket hybrid. A poncharflet. A blanchosca. A scarponket. And it matches EVERYTHING. It's like she was auditioning for Pan Am seven years too early.
Leelee Sobieski, July 2004
She was really into hybrid outfits, apparently, because this has some kind of neckerchief. And lest you think otherwise, I BELIEVE the "straps" on the dress are actually her bra, which she is trying to pass off as part of the outfit. Nice try, Leelee. You almost had me fooled.
Leelee Sobieski, January 2005
What rodeo is THIS for? The Association for American Newsreaders Who Like Roping Stories and Steers?
Leelee Sobieski, June 2005
We've learned now, twice, that Leelee has a fetish for making sure you can see her bra. This is the first time we learned she also believes you need to understand her panties. She looks like a seriously ... altered... Coachella picnic.
Leelee Sobieski, October 2006
This is at least a little more fun. I'm especially intrigued at how her Mary Janes remind me of bowling shoes.
Leelee Sobieski, October 2006
You know, you don't have to dress up for the Sound of Music tour, but it's sort of a fun idea I suppose. How do I break it to her that they don't let people leap across the gazebo benches like Liesl did because some old lady fell and broke her hip?
Leelee Sobieski, Februrary 2007
HELLO. By this point, even though she was working, most people had lost track of her, since there was no need for a Young Helen Hunt anymore. Apparently somebody decided it was time to ring our bells. At least her hair and makeup, for once, are totally working.
Leelee Sobieski, February 2007
I kind of like this, although I wish she'd put a little more effort into shoes that hipped it up. Those look like she bought them at Brass Plum in Nordstrom -- which is FINE, unless you are a movie star at the Oscars, in which case you get someone to borrow you something from the Saks shoe floor.
Leelee Sobieski, June 2007
I remember when I first saw this outfit. I was pretty sure it was mankind's most hideous idea. HA. Oh, how little I knew. How innocent I was. How pre-Gaga, pre-Perry, pre-Amber Rose... I'm sure the fine people at Playtex were like, "Wait, what? We make outerwear now?"
Leelee Sobieski, September 2007
Okay, this dress is fine, but this girl is back to being in dire need of a hot-oil treatment and some Ponds.
Leelee Sobieski, April 2008
Hmm. It's sort of half-biker, half-Medieval-flavored chastity belt. I don't hate it, but maybe that's because she spent more than thirty seconds on her hair.
Leelee Sobieski, April 2008
For $20, she'll make you a seriously kick-ass love potion. The extra side of pink bra is free.
Leelee Sobieski, April 2008
Wow, from studded skirt to demi-robes to a fedora. I suppose we should be glad she didn't try to wear them all together.
Leelee Sobieski, September 2008
At this point, I am thinking, "Where WERE WE when she was wearing all this stuff?" Seriously, did I just develop a blind spot that was Leelee-shaped? Her sleeve is bandaged to her thumb! She is wearing a ringmaster's tiny jacket! And I want her shoes! Why was I not busy working through these strange feelings back in 2008?
Leelee Sobieski, October 2008
Apparently this was Leelee's Sharon Stone phase, where her hair looked like she molded it out of post-sex hay she grabbed from a soap-opera set. But I'm more intrigued that she glued her giant shirt tails together to create a large vaginal-style opening that reminds you of all your, er, basic instincts. Like, say, the basic instinct that wearing a shirt like this is really stupid because getting in and out of it must be annoying, and also, you don't need to put crotch windows into your clothes.
Leelee Sobieski, October 2008
Raise your hand if you know how to find a cropped pea-coat with a HOOD, and matching bermuda shorts. ... Yep, thought so. If Pat Field costumed a remake of Oliver, this would be the Artful Dodger.
Leelee Sobieski, November 2008
Caftantastic! Maybe those last two outfits -- plus most of the others -- were all just leading up to a time when she desensitized us enough that we'd accept her caftanic yens.
Leelee Sobieski, December 2008
I suddenly desperately wish someone had done a Golden Girls prequel.
Leelee Sobieski, May 2010
We took a wee pregnancy break, and then Leelee came back in a really cute, summery, bright skirt. The shoes might not be right with this, but I like the basic outfit -- I mean, it's certainly enough to distract you from the fact that the poster implies she had to get snuggly with Jamie Kennedy, who looks perpetually like he just rolled out of electroshock therapy and into three breakfast burritos.
Leelee Sobieski, October 2010
To me this says, "LOOK. REMEMBER ME? I LOST MY BABY WEIGHT AND I'M ALL GROWED UP AND I NEED A MULLIGAN ON BASICALLY THE LAST EIGHT YEARS. Maybe nine. Or even ten, because frankly, Never Been Kissed was kind of infuriating."
Leelee Sobieski, December 2010
This is a wee bit leggy, but she can certainly pull it off -- it's a very sophisticated look, right down to actual awesome makeup. I suspect someone came back from her baby break with an entirely new team. That, or her son was born with a LOT of really fast-developing skills in the facial arts.
Leelee Sobieski, May 2011
The makeup gods giveth, the makeup gods taketh away.
Leelee Sobieski, May 2011
I really like this, too. It's caftan-adjacent, but also graceful and flattering. She's so TALL. I never really paid attention before because she was too busy begging for us to stare at her bra.
Leelee Sobieski, May 2011
Remember the Sling Dress? It made the rounds in 2008, on Lucy Liu and Amber Heard and Katie Holmes. I'm still sort of lukewarm on the concept -- like, unless you are smuggling a keg or triplets, what is the need? -- but I do like the booties Leelee paired with it. Shoes can be a girl's best friend.
Leelee Sobieski, June 2011
This, though, I really love. A slightly more true-red or dark red lip might've been more striking with it, a la all the other ladies who copied Michelle Williams from that Oscar year, but the haircut is tremendous. She's come a long way from magic carpet bodices and Playtex pantsuits and see-through blankets that appear to have lived through a thousand hallucinatory funks. I like where this has gone; let's see now where else it goes.